char = R;code = 82
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = e;code = 101
char = r;code = 114
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ,;code = 44
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = -;code = 45
char = s;code = 115
char = c;code = 99
char = a;code = 97
char = v;code = 118
char = e;code = 101
char = n;code = 110
char = g;code = 103
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = c;code = 99
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = e;code = 101
char = u;code = 117
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = -;code = 45
char = r;code = 114
char = e;code = 101
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = s;code = 115
char = .;code = 46
result sql = Radical generation, radical-scavenging activity, and cytotoxicity of eugenol-related compounds.
Radical generation, radical-scavenging activity, and cytotoxicity of eugenol-related compounds.
char = T;code = 84
char = o;code = 111
char = ;code = 32
char = c;code = 99
char = l;code = 108
char = a;code = 97
char = r;code = 114
char = i;code = 105
char = f;code = 102
char = y;code = 121
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = p;code = 112
char = o;code = 111
char = s;code = 115
char = s;code = 115
char = i;code = 105
char = b;code = 98
char = l;code = 108
char = e;code = 101
char = ;code = 32
char = l;code = 108
char = i;code = 105
char = n;code = 110
char = k;code = 107
char = ;code = 32
char = b;code = 98
char = e;code = 101
char = t;code = 116
char = w;code = 119
char = e;code = 101
char = e;code = 101
char = n;code = 110
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = c;code = 99
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = e;code = 101
char = u;code = 117
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = -;code = 45
char = r;code = 114
char = e;code = 101
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = m;code = 109
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = s;code = 115
char = y;code = 121
char = n;code = 110
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = s;code = 115
char = i;code = 105
char = z;code = 122
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = f;code = 102
char = r;code = 114
char = o;code = 111
char = m;code = 109
char = ;code = 32
char = e;code = 101
char = u;code = 117
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = ;code = 32
char = (;code = 40
char = 4;code = 52
char = -;code = 45
char = a;code = 97
char = l;code = 108
char = l;code = 108
char = y;code = 121
char = l;code = 108
char = -;code = 45
char = 2;code = 50
char = -;code = 45
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = -;code = 45
char = p;code = 112
char = h;code = 104
char = e;code = 101
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = b;code = 98
char = u;code = 117
char = t;code = 116
char = y;code = 121
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = h;code = 104
char = y;code = 121
char = d;code = 100
char = r;code = 114
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = a;code = 97
char = n;code = 110
char = i;code = 105
char = s;code = 115
char = o;code = 111
char = l;code = 108
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = B;code = 66
char = H;code = 72
char = A;code = 65
char = );code = 41
char = ;code = 32
char = (;code = 40
char = 2;code = 50
char = -;code = 45
char = t;code = 116
char = -;code = 45
char = b;code = 98
char = u;code = 117
char = t;code = 116
char = y;code = 121
char = l;code = 108
char = -;code = 45
char = 4;code = 52
char = -;code = 45
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = p;code = 112
char = h;code = 104
char = e;code = 101
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = );code = 41
char = ;code = 32
char = o;code = 111
char = r;code = 114
char = ;code = 32
char = M;code = 77
char = M;code = 77
char = P;code = 80
char = ;code = 32
char = (;code = 40
char = 2;code = 50
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = -;code = 45
char = 4;code = 52
char = -;code = 45
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = p;code = 112
char = h;code = 104
char = e;code = 101
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = );code = 41
char = ;;code = 59
char = ;code = 32
char = b;code = 98
char = i;code = 105
char = s;code = 115
char = -;code = 45
char = E;code = 69
char = U;code = 85
char = G;code = 71
char = ;code = 32
char = (;code = 40
char = 3;code = 51
char = ,;code = 44
char = 3;code = 51
char = ';code = 39
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = -;code = 45
char = 5;code = 53
char = ,;code = 44
char = 5;code = 53
char = ';code = 39
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = -;code = 45
char = 2;code = 50
char = -;code = 45
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = p;code = 112
char = e;code = 101
char = n;code = 110
char = y;code = 121
char = l;code = 108
char = -;code = 45
char = 1;code = 49
char = ,;code = 44
char = 1;code = 49
char = ';code = 39
char = -;code = 45
char = b;code = 98
char = i;code = 105
char = p;code = 112
char = h;code = 104
char = e;code = 101
char = n;code = 110
char = y;code = 121
char = l;code = 108
char = -;code = 45
char = 2;code = 50
char = ,;code = 44
char = 2;code = 50
char = ';code = 39
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = o;code = 111
char = l;code = 108
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = b;code = 98
char = i;code = 105
char = s;code = 115
char = -;code = 45
char = B;code = 66
char = H;code = 72
char = A;code = 65
char = ;code = 32
char = (;code = 40
char = 3;code = 51
char = ,;code = 44
char = 3;code = 51
char = ';code = 39
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = -;code = 45
char = t;code = 116
char = -;code = 45
char = b;code = 98
char = u;code = 117
char = t;code = 116
char = y;code = 121
char = l;code = 108
char = -;code = 45
char = 5;code = 53
char = ,;code = 44
char = 5;code = 53
char = ';code = 39
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = -;code = 45
char = 1;code = 49
char = ,;code = 44
char = 1;code = 49
char = ';code = 39
char = -;code = 45
char = b;code = 98
char = i;code = 105
char = p;code = 112
char = h;code = 104
char = e;code = 101
char = n;code = 110
char = y;code = 121
char = l;code = 108
char = -;code = 45
char = 2;code = 50
char = ,;code = 44
char = 2;code = 50
char = ';code = 39
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = o;code = 111
char = l;code = 108
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = b;code = 98
char = i;code = 105
char = s;code = 115
char = -;code = 45
char = M;code = 77
char = M;code = 77
char = P;code = 80
char = ;code = 32
char = (;code = 40
char = 3;code = 51
char = ,;code = 44
char = 3;code = 51
char = ';code = 39
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = -;code = 45
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = -;code = 45
char = 5;code = 53
char = ,;code = 44
char = 5;code = 53
char = ';code = 39
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
char = -;code = 45
char = 1;code = 49
char = ,;code = 44
char = 1;code = 49
char = ';code = 39
char = -;code = 45
char = b;code = 98
char = i;code = 105
char = p;code = 112
char = h;code = 104
char = e;code = 101
char = n;code = 110
char = y;code = 121
char = l;code = 108
char = -;code = 45
char = 2;code = 50
char = ,;code = 44
char = 2;code = 50
char = ';code = 39
char = -;code = 45
char = d;code = 100
char = i;code = 105
char = o;code = 111
char = l;code = 108
char = );code = 41
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = s;code = 115
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = d;code = 100
char = e;code = 101
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char = e;code = 101
char = r;code = 114
char = m;code = 109
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = u;code = 117
char = s;code = 115
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = s;code = 115
char = a;code = 97
char = l;code = 108
char = i;code = 105
char = v;code = 118
char = a;code = 97
char = r;code = 114
char = y;code = 121
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char = g;code = 103
char = l;code = 108
char = a;code = 97
char = n;code = 110
char = d;code = 100
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char = t;code = 116
char = u;code = 117
char = m;code = 109
char = o;code = 111
char = r;code = 114
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char = c;code = 99
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char = l;code = 108
char = l;code = 108
char = ;code = 32
char = l;code = 108
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = H;code = 72
char = S;code = 83
char = G;code = 71
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = o;code = 111
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char = a;code = 97
char = l;code = 108
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char = s;code = 115
char = q;code = 113
char = u;code = 117
char = a;code = 97
char = m;code = 109
char = o;code = 111
char = u;code = 117
char = s;code = 115
char = ;code = 32
char = c;code = 99
char = e;code = 101
char = l;code = 108
char = l;code = 108
char = ;code = 32
char = c;code = 99
char = a;code = 97
char = r;code = 114
char = c;code = 99
char = i;code = 105
char = n;code = 110
char = o;code = 111
char = m;code = 109
char = a;code = 97
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char = c;code = 99
char = e;code = 101
char = l;code = 108
char = l;code = 108
char = ;code = 32
char = l;code = 108
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = H;code = 72
char = S;code = 83
char = C;code = 67
char = -;code = 45
char = 2;code = 50
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char = ;code = 32
char = a;code = 97
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char = d;code = 100
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char = h;code = 104
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char = a;code = 97
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char = p;code = 112
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char = e;code = 101
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char = i;code = 105
char = c;code = 99
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char = l;code = 108
char = e;code = 101
char = u;code = 117
char = k;code = 107
char = e;code = 101
char = m;code = 109
char = i;code = 105
char = a;code = 97
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char = c;code = 99
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char = l;code = 108
char = l;code = 108
char = ;code = 32
char = l;code = 108
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = H;code = 72
char = L;code = 76
char = -;code = 45
char = 6;code = 54
char = 0;code = 48
char = );code = 41
char = .;code = 46
char = ;code = 32
char = A;code = 65
char = ;code = 32
char = p;code = 112
char = a;code = 97
char = r;code = 114
char = a;code = 97
char = b;code = 98
char = o;code = 111
char = l;code = 108
char = i;code = 105
char = c;code = 99
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char = r;code = 114
char = e;code = 101
char = l;code = 108
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
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char = s;code = 115
char = h;code = 104
char = i;code = 105
char = p;code = 112
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char = b;code = 98
char = e;code = 101
char = t;code = 116
char = w;code = 119
char = e;code = 101
char = e;code = 101
char = n;code = 110
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = c;code = 99
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = l;code = 108
char = o;code = 111
char = g;code = 103
char = ;code = 32
char = P;code = 80
char = ;code = 32
char = (;code = 40
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = o;code = 111
char = c;code = 99
char = t;code = 116
char = a;code = 97
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char = o;code = 111
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char = a;code = 97
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char = e;code = 101
char = r;code = 114
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char = a;code = 97
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char = i;code = 105
char = t;code = 116
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char = o;code = 111
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char = c;code = 99
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char = f;code = 102
char = f;code = 102
char = i;code = 105
char = c;code = 99
char = i;code = 105
char = e;code = 101
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char = t;code = 116
char = );code = 41
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char = w;code = 119
char = a;code = 97
char = s;code = 115
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char = o;code = 111
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char = s;code = 115
char = e;code = 101
char = r;code = 114
char = v;code = 118
char = e;code = 101
char = d;code = 100
char = ,;code = 44
char = ;code = 32
char = s;code = 115
char = h;code = 104
char = o;code = 111
char = w;code = 119
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = b;code = 98
char = o;code = 111
char = t;code = 116
char = h;code = 104
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char = B;code = 66
char = H;code = 72
char = A;code = 65
char = ;code = 32
char = a;code = 97
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char = d;code = 100
char = ;code = 32
char = b;code = 98
char = i;code = 105
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char = M;code = 77
char = M;code = 77
char = P;code = 80
char = ,;code = 44
char = ;code = 32
char = w;code = 119
char = i;code = 105
char = t;code = 116
char = h;code = 104
char = ;code = 32
char = a;code = 97
char = ;code = 32
char = l;code = 108
char = o;code = 111
char = g;code = 103
char = ;code = 32
char = P;code = 80
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = 3;code = 51
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char = 4;code = 52
char = ,;code = 44
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = m;code = 109
char = o;code = 111
char = s;code = 115
char = t;code = 116
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = c;code = 99
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = y;code = 121
char = t;code = 116
char = o;code = 111
char = t;code = 116
char = o;code = 111
char = x;code = 120
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = 2;code = 50
char = -;code = 45
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = v;code = 118
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = s;code = 115
char = ,;code = 44
char = ;code = 32
char = e;code = 101
char = u;code = 117
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = ,;code = 44
char = ;code = 32
char = M;code = 77
char = M;code = 77
char = P;code = 80
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = b;code = 98
char = i;code = 105
char = s;code = 115
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char = M;code = 77
char = M;code = 77
char = P;code = 80
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = g;code = 103
char = a;code = 97
char = i;code = 105
char = n;code = 110
char = s;code = 115
char = t;code = 116
char = ;code = 32
char = H;code = 72
char = S;code = 83
char = G;code = 71
char = ;code = 32
char = c;code = 99
char = e;code = 101
char = l;code = 108
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = s;code = 115
char = i;code = 105
char = g;code = 103
char = n;code = 110
char = i;code = 105
char = f;code = 102
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = n;code = 110
char = t;code = 116
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = e;code = 101
char = n;code = 110
char = h;code = 104
char = a;code = 97
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = b;code = 98
char = y;code = 121
char = ;code = 32
char = v;code = 118
char = i;code = 105
char = s;code = 115
char = i;code = 105
char = b;code = 98
char = l;code = 108
char = e;code = 101
char = -;code = 45
char = l;code = 108
char = i;code = 105
char = g;code = 103
char = h;code = 104
char = t;code = 116
char = ;code = 32
char = i;code = 105
char = r;code = 114
char = r;code = 114
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ,;code = 44
char = ;code = 32
char = p;code = 112
char = o;code = 111
char = s;code = 115
char = s;code = 115
char = i;code = 105
char = b;code = 98
char = l;code = 108
char = y;code = 121
char = ;code = 32
char = d;code = 100
char = u;code = 117
char = e;code = 101
char = ;code = 32
char = t;code = 116
char = o;code = 111
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = i;code = 105
char = r;code = 114
char = ;code = 32
char = h;code = 104
char = i;code = 105
char = g;code = 103
char = h;code = 104
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = d;code = 100
char = o;code = 111
char = x;code = 120
char = ;code = 32
char = p;code = 112
char = o;code = 111
char = t;code = 116
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = a;code = 97
char = l;code = 108
char = .;code = 46
char = ;code = 32
char = E;code = 69
char = l;code = 108
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = s;code = 115
char = p;code = 112
char = i;code = 105
char = n;code = 110
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = s;code = 115
char = o;code = 111
char = n;code = 110
char = a;code = 97
char = n;code = 110
char = c;code = 99
char = e;code = 101
char = ;code = 32
char = (;code = 40
char = E;code = 69
char = S;code = 83
char = R;code = 82
char = );code = 41
char = ;code = 32
char = s;code = 115
char = p;code = 112
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = r;code = 114
char = o;code = 111
char = s;code = 115
char = c;code = 99
char = o;code = 111
char = p;code = 112
char = y;code = 121
char = ;code = 32
char = i;code = 105
char = n;code = 110
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = t;code = 116
char = ;code = 32
char = e;code = 101
char = u;code = 117
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = ;code = 32
char = a;code = 97
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char = d;code = 100
char = ;code = 32
char = B;code = 66
char = H;code = 72
char = A;code = 65
char = ;code = 32
char = a;code = 97
char = l;code = 108
char = o;code = 111
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = d;code = 100
char = u;code = 117
char = c;code = 99
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = r;code = 114
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = s;code = 115
char = ;code = 32
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = e;code = 101
char = r;code = 114
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char = a;code = 97
char = l;code = 108
char = k;code = 107
char = a;code = 97
char = l;code = 108
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = n;code = 110
char = d;code = 100
char = i;code = 105
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = s;code = 115
char = ;code = 32
char = (;code = 40
char = p;code = 112
char = H;code = 72
char = ;code = 32
char = >;code = 62
char = ;code = 32
char = 9;code = 57
char = .;code = 46
char = 5;code = 53
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = a;code = 97
char = n;code = 110
char = d;code = 100
char = ;code = 32
char = e;code = 101
char = u;code = 117
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = o;code = 111
char = l;code = 108
char = ;code = 32
char = m;code = 109
char = o;code = 111
char = s;code = 115
char = t;code = 116
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char = e;code = 101
char = f;code = 102
char = f;code = 102
char = i;code = 105
char = c;code = 99
char = i;code = 105
char = e;code = 101
char = n;code = 110
char = t;code = 116
char = l;code = 108
char = y;code = 121
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char = s;code = 115
char = c;code = 99
char = a;code = 97
char = v;code = 118
char = e;code = 101
char = n;code = 110
char = g;code = 103
char = e;code = 101
char = s;code = 115
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char = r;code = 114
char = e;code = 101
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
char = ;code = 32
char = o;code = 111
char = x;code = 120
char = y;code = 121
char = g;code = 103
char = e;code = 101
char = n;code = 110
char = ;code = 32
char = s;code = 115
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char = e;code = 101
char = c;code = 99
char = i;code = 105
char = e;code = 101
char = s;code = 115
char = ;code = 32
char = (;code = 40
char = O;code = 79
char = 2;code = 50
char = -;code = 45
char = );code = 41
char = .;code = 46
char = ;code = 32
char = A;code = 65
char = n;code = 110
char = t;code = 116
char = i;code = 105
char = o;code = 111
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char = i;code = 105
char = d;code = 100
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = e;code = 101
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char = r;code = 114
char = e;code = 101
char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = v;code = 118
char = i;code = 105
char = t;code = 116
char = y;code = 121
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char = o;code = 111
char = f;code = 102
char = ;code = 32
char = e;code = 101
char = u;code = 117
char = g;code = 103
char = e;code = 101
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char = o;code = 111
char = l;code = 108
char = -;code = 45
char = r;code = 114
char = e;code = 101
char = l;code = 108
char = a;code = 97
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char = e;code = 101
char = d;code = 100
char = ;code = 32
char = c;code = 99
char = o;code = 111
char = m;code = 109
char = p;code = 112
char = o;code = 111
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = s;code = 115
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = t;code = 116
char = e;code = 101
char = r;code = 114
char = m;code = 109
char = i;code = 105
char = n;code = 110
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = b;code = 98
char = y;code = 121
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char = m;code = 109
char = e;code = 101
char = a;code = 97
char = s;code = 115
char = u;code = 117
char = r;code = 114
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
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char = i;code = 105
char = n;code = 110
char = h;code = 104
char = i;code = 105
char = b;code = 98
char = i;code = 105
char = t;code = 116
char = i;code = 105
char = n;code = 110
char = g;code = 103
char = ;code = 32
char = p;code = 112
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = o;code = 111
char = d;code = 100
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = A;code = 65
char = I;code = 73
char = B;code = 66
char = N;code = 78
char = ;code = 32
char = (;code = 40
char = 2;code = 50
char = ,;code = 44
char = 2;code = 50
char = ';code = 39
char = -;code = 45
char = a;code = 97
char = z;code = 122
char = o;code = 111
char = b;code = 98
char = i;code = 105
char = s;code = 115
char = i;code = 105
char = s;code = 115
char = o;code = 111
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char = u;code = 117
char = t;code = 116
char = y;code = 121
char = r;code = 114
char = o;code = 111
char = n;code = 110
char = i;code = 105
char = t;code = 116
char = r;code = 114
char = i;code = 105
char = l;code = 108
char = e;code = 101
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char = /;code = 47
char = M;code = 77
char = M;code = 77
char = A;code = 65
char = ;code = 32
char = (;code = 40
char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = y;code = 121
char = l;code = 108
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char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = a;code = 97
char = c;code = 99
char = r;code = 114
char = y;code = 121
char = l;code = 108
char = a;code = 97
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char = e;code = 101
char = );code = 41
char = ;code = 32
char = p;code = 112
char = o;code = 111
char = l;code = 108
char = y;code = 121
char = m;code = 109
char = e;code = 101
char = r;code = 114
char = i;code = 105
char = z;code = 122
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
char = n;code = 110
char = ;code = 32
char = s;code = 115
char = y;code = 121
char = s;code = 115
char = t;code = 116
char = e;code = 101
char = m;code = 109
char = ,;code = 44
char = ;code = 32
char = a;code = 97
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char = d;code = 100
char = ;code = 32
char = t;code = 116
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char = e;code = 101
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char = u;code = 117
char = m;code = 109
char = b;code = 98
char = e;code = 101
char = r;code = 114
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char = f;code = 102
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char = o;code = 111
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char = e;code = 101
char = s;code = 115
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char = o;code = 111
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char = ;code = 32
char = p;code = 112
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char = r;code = 114
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char = i;code = 105
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char = p;code = 112
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char = s;code = 115
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char = e;code = 101
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char = a;code = 97
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char = t;code = 116
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char = h;code = 104
char = e;code = 101
char = n;code = 110
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char = s;code = 115
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char = s;code = 115
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char = o;code = 111
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char = i;code = 105
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char = e;code = 101
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char = r;code = 114
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char = f;code = 102
char = a;code = 97
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char = t;code = 116
char = o;code = 111
char = r;code = 114
char = ,;code = 44
char = ;code = 32
char = n;code = 110
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char = .;code = 46
char = ;code = 32
char = I;code = 73
char = t;code = 116
char = ;code = 32
char = w;code = 119
char = a;code = 97
char = s;code = 115
char = ;code = 32
char = f;code = 102
char = o;code = 111
char = u;code = 117
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char = t;code = 116
char = h;code = 104
char = a;code = 97
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char = t;code = 116
char = h;code = 104
char = e;code = 101
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char = v;code = 118
char = a;code = 97
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char = u;code = 117
char = e;code = 101
char = s;code = 115
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char = o;code = 111
char = f;code = 102
char = ;code = 32
char = e;code = 101
char = u;code = 117
char = g;code = 103
char = e;code = 101
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char = o;code = 111
char = l;code = 108
char = ;code = 32
char = a;code = 97
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char = d;code = 100
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char = M;code = 77
char = M;code = 77
char = P;code = 80
char = ;code = 32
char = w;code = 119
char = e;code = 101
char = r;code = 114
char = e;code = 101
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char = a;code = 97
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char = p;code = 112
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char = x;code = 120
char = i;code = 105
char = m;code = 109
char = a;code = 97
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char = e;code = 101
char = l;code = 108
char = y;code = 121
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char = e;code = 101
char = r;code = 114
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char = a;code = 97
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char = t;code = 116
char = h;code = 104
char = o;code = 111
char = s;code = 115
char = e;code = 101
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char = o;code = 111
char = f;code = 102
char = ;code = 32
char = B;code = 66
char = H;code = 72
char = A;code = 65
char = ;code = 32
char = >;code = 62
char = 2;code = 50
char = ,;code = 44
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = g;code = 103
char = g;code = 103
char = e;code = 101
char = s;code = 115
char = t;code = 116
char = i;code = 105
char = n;code = 110
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char = ;code = 32
char = t;code = 116
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char = a;code = 97
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char = ;code = 32
char = e;code = 101
char = u;code = 117
char = g;code = 103
char = e;code = 101
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char = o;code = 111
char = l;code = 108
char = ;code = 32
char = a;code = 97
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char = d;code = 100
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char = M;code = 77
char = M;code = 77
char = P;code = 80
char = ;code = 32
char = u;code = 117
char = n;code = 110
char = d;code = 100
char = e;code = 101
char = r;code = 114
char = g;code = 103
char = o;code = 111
char = ;code = 32
char = d;code = 100
char = i;code = 105
char = m;code = 109
char = e;code = 101
char = r;code = 114
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char = z;code = 122
char = a;code = 97
char = t;code = 116
char = i;code = 105
char = o;code = 111
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char = t;code = 116
char = h;code = 104
char = r;code = 114
char = o;code = 111
char = u;code = 117
char = g;code = 103
char = h;code = 104
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char = r;code = 114
char = a;code = 97
char = d;code = 100
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = -;code = 45
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result sql = To clarify the possible link between radicals and cytotoxicity of eugenol-related compounds, dimeric compounds were synthesized from eugenol (4-allyl-2-methoxy-phenol), butylated hydroxyanisole (BHA) (2-t-butyl-4-methoxyphenol) or MMP (2 methoxy-4-methylphenol); bis-EUG (3,3'-dimethoxy-5,5'-di-2-propenyl-1,1'-biphenyl-2,2'-diol), bis-BHA (3,3'-di-t-butyl-5,5'-dimethoxy-1,1'-biphenyl-2,2'-diol), and bis-MMP (3,3'-di-methoxy-5,5'-dimethyl-1,1'-biphenyl-2,2'-diol). The cytotoxic activity of these compounds was determined using a salivary gland tumor cell line (HSG), oral squamous cell carcinoma cell line (HSC-2) and human promyelocytic leukemia cell line (HL-60). A parabolic relationship between the cytotoxicity and log P (the octanol-water partition coefficient) was observed, showing that both BHA and bis-MMP, with a log P of 3-4, were the most cytotoxic. The cytotoxic activity of the 2-methoxy derivatives, eugenol, MMP and bis-MMP, against HSG cells was significantly enhanced by visible-light irradiation, possibly due to their high redox potential. Electron spin resonance (ESR) spectroscopy indicated that eugenol and BHA alone produced radicals under alkaline conditions (pH > 9.5), and eugenol most efficiently scavenges reactive oxygen species (O2-). Antioxidative reactivity of eugenol-related compounds was determined by measuring the inhibiting periods of the AIBN (2,2'-azobisisobutyronitrile)/MMA (methyl methacrylate) polymerization system, and the number of moles of peroxy radical trapped by moles of the relevant phenols (stoichiometric factor, n). It was found that the n values of eugenol and MMP were approximately 1, whereas those of BHA >2, suggesting that eugenol and MMP undergo dimerization through radical-radical couplings through quinone methides, whereas BHA undergoes the competitive interaction with poly-MMA radicals after oxidation by AIBN-peroxy radicals. BHA was an efficient peroxy radical-scavenger, but possibly reacted with polymer radicals of the lipid, thus mediating the cytotoxicity. The n value of bis-BHA was two, whereas those of bis-EUG and bis-MMP were 1.6-1.7, suggesting that the latter were further oxidized. The enthalpies of phenoxyl radical formation were determined using the semi-empirical PM3 quantum-mechanical method and the possible link to redox potential was discussed.

Publication: In Vitr Mol Toxicol 2000 Winter ;13(4)::269-80.
Publication Date: 2000 Winter
Study Author(s): Fujisawa, S;Atsumi, T;Satoh, K;Kadoma, Y;Ishihara, M;Okada, N;Nagasaki, M;Yokoe, I;Sakagami, H;
Institution: Department of Oral Diagnosis, Meikai University School of Dentistry, Saitama, Japan. [email protected]
Shortcut link to this study:
To clarify the possible link between radicals and cytotoxicity of eugenol-related compounds, dimeric compounds were synthesized from eugenol (4-allyl-2-methoxy-phenol), butylated hydroxyanisole (BHA) (2-t-butyl-4-methoxyphenol) or MMP (2 methoxy-4-methylphenol); bis-EUG (3,3'-dimethoxy-5,5'-di-2-propenyl-1,1'-biphenyl-2,2'-diol), bis-BHA (3,3'-di-t-butyl-5,5'-dimethoxy-1,1'-biphenyl-2,2'-diol), and bis-MMP (3,3'-di-methoxy-5,5'-dimethyl-1,1'-biphenyl-2,2'-diol). The cytotoxic activity of these compounds was determined using a salivary gland tumor cell line (HSG), oral squamous cell carcinoma cell line (HSC-2) and human promyelocytic leukemia cell line (HL-60). A parabolic relationship between the cytotoxicity and log P (the octanol-water partition coefficient) was observed, showing that both BHA and bis-MMP, with a log P of 3-4, were the most cytotoxic. The cytotoxic activity of the 2-methoxy derivatives, eugenol, MMP and bis-MMP, against HSG cells was significantly enhanced by visible-light irradiation, possibly due to their high redox potential. Electron spin resonance (ESR) spectroscopy indicated that eugenol and BHA alone produced radicals under alkaline conditions (pH > 9.5), and eugenol most efficiently scavenges reactive oxygen species (O2-). Antioxidative reactivity of eugenol-related compounds was determined by measuring the inhibiting periods of the AIBN (2,2'-azobisisobutyronitrile)/MMA (methyl methacrylate) polymerization system, and the number of moles of peroxy radical trapped by moles of the relevant phenols (stoichiometric factor, n). It was found that the n values of eugenol and MMP were approximately 1, whereas those of BHA >2, suggesting that eugenol and MMP undergo dimerization through radical-radical couplings through quinone methides, whereas BHA undergoes the competitive interaction with poly-MMA radicals after oxidation by AIBN-peroxy radicals. BHA was an efficient peroxy radical-scavenger, but possibly reacted with polymer radicals of the lipid, thus mediating the cytotoxicity. The n value of bis-BHA was two, whereas those of bis-EUG and bis-MMP were 1.6-1.7, suggesting that the latter were further oxidized. The enthalpies of phenoxyl radical formation were determined using the semi-empirical PM3 quantum-mechanical method and the possible link to redox potential was discussed.
PMID: 11319278

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