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result sql = New biomarkers for monitoring the levels of isothiocyanates in humans.
New biomarkers for monitoring the levels of isothiocyanates in humans.
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char = i;code = 105
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char = a;code = 97
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char = e;code = 101
char = s;code = 115
char = .;code = 46
char = ;code = 32
char = U;code = 85
char = r;code = 114
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char = n;code = 110
char = a;code = 97
char = r;code = 114
char = y;code = 121
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char = e;code = 101
char = t;code = 116
char = a;code = 97
char = b;code = 98
char = o;code = 111
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char = i;code = 105
char = t;code = 116
char = e;code = 101
char = s;code = 115
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char = m;code = 109
char = i;code = 105
char = g;code = 103
char = h;code = 104
char = t;code = 116
char = ;code = 32
char = p;code = 112
char = r;code = 114
char = o;code = 111
char = v;code = 118
char = i;code = 105
char = d;code = 100
char = e;code = 101
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char = t;code = 116
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char = e;code = 101
char = ;code = 32
char = e;code = 101
char = x;code = 120
char = p;code = 112
char = o;code = 111
char = s;code = 115
char = u;code = 117
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = h;code = 104
char = i;code = 105
char = s;code = 115
char = t;code = 116
char = o;code = 111
char = r;code = 114
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 = l;code = 108
char = a;code = 97
char = s;code = 115
char = t;code = 116
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char = 2;code = 50
char = 4;code = 52
char = ;code = 32
char = h;code = 104
char = ,;code = 44
char = ;code = 32
char = i;code = 105
char = f;code = 102
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = u;code = 117
char = r;code = 114
char = i;code = 105
char = n;code = 110
char = e;code = 101
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
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char = f;code = 102
char = u;code = 117
char = l;code = 108
char = l;code = 108
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char = n;code = 110
char = e;code = 101
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char = d;code = 100
char = a;code = 97
char = y;code = 121
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char = i;code = 105
char = s;code = 115
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char = c;code = 99
char = o;code = 111
char = l;code = 108
char = l;code = 108
char = e;code = 101
char = c;code = 99
char = t;code = 116
char = e;code = 101
char = d;code = 100
char = .;code = 46
char = ;code = 32
char = H;code = 72
char = o;code = 111
char = w;code = 119
char = e;code = 101
char = v;code = 118
char = e;code = 101
char = r;code = 114
char = ,;code = 44
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = i;code = 105
char = s;code = 115
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char = i;code = 105
char = s;code = 115
char = ;code = 32
char = n;code = 110
char = o;code = 111
char = t;code = 116
char = ;code = 32
char = f;code = 102
char = e;code = 101
char = a;code = 97
char = s;code = 115
char = i;code = 105
char = b;code = 98
char = l;code = 108
char = e;code = 101
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char = i;code = 105
char = n;code = 110
char = ;code = 32
char = l;code = 108
char = a;code = 97
char = r;code = 114
char = g;code = 103
char = e;code = 101
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char = e;code = 101
char = p;code = 112
char = i;code = 105
char = d;code = 100
char = e;code = 101
char = m;code = 109
char = i;code = 105
char = o;code = 111
char = l;code = 108
char = o;code = 111
char = g;code = 103
char = i;code = 105
char = c;code = 99
char = a;code = 97
char = l;code = 108
char = ;code = 32
char = s;code = 115
char = t;code = 116
char = u;code = 117
char = d;code = 100
char = i;code = 105
char = e;code = 101
char = s;code = 115
char = .;code = 46
char = ;code = 32
char = F;code = 70
char = u;code = 117
char = r;code = 114
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = r;code = 114
char = m;code = 109
char = o;code = 111
char = r;code = 114
char = e;code = 101
char = ,;code = 44
char = ;code = 32
char = t;code = 116
char = h;code = 104
char = e;code = 101
char = ;code = 32
char = m;code = 109
char = e;code = 101
char = r;code = 114
char = c;code = 99
char = a;code = 97
char = p;code = 112
char = t;code = 116
char = u;code = 117
char = r;code = 114
char = i;code = 105
char = c;code = 99
char = ;code = 32
char = a;code = 97
char = c;code = 99
char = i;code = 105
char = d;code = 100
char = s;code = 115
char = ;code = 32
char = o;code = 111
char = f;code = 102
char = ;code = 32
char = I;code = 73
char = T;code = 84
char = C;code = 67
char = ;code = 32
char = a;code = 97
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = n;code = 110
char = o;code = 111
char = t;code = 116
char = ;code = 32
char = s;code = 115
char = t;code = 116
char = a;code = 97
char = b;code = 98
char = l;code = 108
char = e;code = 101
char = .;code = 46
char = ;code = 32
char = T;code = 84
char = h;code = 104
char = e;code = 101
char = r;code = 114
char = e;code = 101
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = e;code = 101
char = ,;code = 44
char = ;code = 32
char = s;code = 115
char = t;code = 116
char = a;code = 97
char = b;code = 98
char = l;code = 108
char = e;code = 101
char = ;code = 32
char = b;code = 98
char = i;code = 105
char = o;code = 111
char = m;code = 109
char = a;code = 97
char = r;code = 114
char = k;code = 107
char = e;code = 101
char = r;code = 114
char = s;code = 115
char = ;code = 32
char = a;code = 97
char = r;code = 114
char = e;code = 101
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char = n;code = 110
char = e;code = 101
char = e;code = 101
char = d;code = 100
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = t;code = 116
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char = a;code = 97
char = t;code = 116
char = ;code = 32
char = r;code = 114
char = e;code = 101
char = f;code = 102
char = l;code = 108
char = e;code = 101
char = c;code = 99
char = t;code = 116
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char = a;code = 97
char = ;code = 32
char = l;code = 108
char = a;code = 97
char = r;code = 114
char = g;code = 103
char = e;code = 101
char = r;code = 114
char = ;code = 32
char = t;code = 116
char = i;code = 105
char = m;code = 109
char = e;code = 101
char = ;code = 32
char = s;code = 115
char = p;code = 112
char = a;code = 97
char = n;code = 110
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 = I;code = 73
char = T;code = 84
char = C;code = 67
char = ;code = 32
char = e;code = 101
char = x;code = 120
char = p;code = 112
char = o;code = 111
char = s;code = 115
char = u;code = 117
char = r;code = 114
char = e;code = 101
char = ;code = 32
char = h;code = 104
char = i;code = 105
char = s;code = 115
char = t;code = 116
char = o;code = 111
char = r;code = 114
char = y;code = 121
char = .;code = 46
char = ;code = 32
char = W;code = 87
char = e;code = 101
char = ;code = 32
char = d;code = 100
char = e;code = 101
char = v;code = 118
char = e;code = 101
char = l;code = 108
char = o;code = 111
char = p;code = 112
char = e;code = 101
char = d;code = 100
char = ;code = 32
char = a;code = 97
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char = m;code = 109
char = e;code = 101
char = t;code = 116
char = h;code = 104
char = o;code = 111
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char = t;code = 116
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char = d;code = 100
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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
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char = s;code = 115
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char = a;code = 97
char = b;code = 98
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char = e;code = 101
char = ;code = 32
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char = t;code = 116
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char = c;code = 99
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char = s;code = 115
char = t;code = 116
char = e;code = 101
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char = n;code = 110
char = e;code = 101
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char = d;code = 100
char = u;code = 117
char = c;code = 99
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char = s;code = 115
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char = ;code = 32
char = r;code = 114
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char = a;code = 97
char = c;code = 99
char = t;code = 116
char = i;code = 105
char = o;code = 111
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char = p;code = 112
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char = o;code = 111
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char = u;code = 117
char = c;code = 99
char = t;code = 116
char = s;code = 115
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char = o;code = 111
char = f;code = 102
char = ;code = 32
char = I;code = 73
char = T;code = 84
char = C;code = 67
char = s;code = 115
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 = l;code = 108
char = b;code = 98
char = u;code = 117
char = m;code = 109
char = i;code = 105
char = n;code = 110
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char = a;code = 97
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char = d;code = 100
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char = h;code = 104
char = e;code = 101
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char = i;code = 105
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char = i;code = 105
char = n;code = 110
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char = h;code = 104
char = u;code = 117
char = m;code = 109
char = a;code = 97
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char = s;code = 115
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char = a;code = 97
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char = d;code = 100
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char = m;code = 109
char = i;code = 105
char = c;code = 99
char = e;code = 101
char = .;code = 46
char = ;code = 32
char = <;code = 60
char = b;code = 98
char = >;code = 62
char = W;code = 87
char = E;code = 69
char = ;code = 32
char = R;code = 82
char = E;code = 69
char = A;code = 65
char = C;code = 67
char = T;code = 84
char = E;code = 69
char = D;code = 68
char = ;code = 32
char = A;code = 65
char = L;code = 76
char = B;code = 66
char = U;code = 85
char = M;code = 77
char = I;code = 73
char = N;code = 78
char = ;code = 32
char = W;code = 87
char = I;code = 73
char = T;code = 84
char = H;code = 72
char = ;code = 32
char = T;code = 84
char = H;code = 72
char = E;code = 69
char = ;code = 32
char = I;code = 73
char = T;code = 84
char = C;code = 67
char = S;code = 83
char = :;code = 58
char = ;code = 32
char = <;code = 60
char = /;code = 47
char = b;code = 98
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char = ;code = 32
char = b;code = 98
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char = y;code = 121
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char = i;code = 105
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char = c;code = 99
char = y;code = 121
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char = (;code = 40
char = B;code = 66
char = I;code = 73
char = T;code = 84
char = C;code = 67
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char = ,;code = 44
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char = p;code = 112
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char = e;code = 101
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char = h;code = 104
char = y;code = 121
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char = ;code = 32
char = i;code = 105
char = s;code = 115
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char = h;code = 104
char = i;code = 105
char = o;code = 111
char = c;code = 99
char = y;code = 121
char = a;code = 97
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char = a;code = 97
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char = e;code = 101
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char = P;code = 80
char = E;code = 69
char = I;code = 73
char = T;code = 84
char = C;code = 67
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = s;code = 115
char = u;code = 117
char = l;code = 108
char = f;code = 102
char = o;code = 111
char = r;code = 114
char = a;code = 97
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char = h;code = 104
char = a;code = 97
char = n;code = 110
char = e;code = 101
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char = (;code = 40
char = S;code = 83
char = F;code = 70
char = N;code = 78
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = a;code = 97
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char = d;code = 100
char = ;code = 32
char = a;code = 97
char = l;code = 108
char = l;code = 108
char = y;code = 121
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char = i;code = 105
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char = o;code = 111
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char = i;code = 105
char = o;code = 111
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char = e;code = 101
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char = (;code = 40
char = A;code = 65
char = I;code = 73
char = T;code = 84
char = C;code = 67
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char = .;code = 46
char = ;code = 32
char = A;code = 65
char = f;code = 102
char = t;code = 116
char = e;code = 101
char = r;code = 114
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char = e;code = 101
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char = z;code = 122
char = y;code = 121
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char = a;code = 97
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char = c;code = 99
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char = g;code = 103
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char = u;code = 117
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char = g;code = 103
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char = L;code = 76
char = C;code = 67
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char = S;code = 83
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char = S;code = 83
char = .;code = 46
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char = <;code = 60
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char = <;code = 60
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char = <;code = 60
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char = H;code = 72
char = E;code = 69
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char = I;code = 73
char = D;code = 68
char = E;code = 69
char = N;code = 78
char = T;code = 84
char = I;code = 73
char = T;code = 84
char = Y;code = 89
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char = O;code = 79
char = F;code = 70
char = ;code = 32
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char = H;code = 72
char = E;code = 69
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char = A;code = 65
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char = D;code = 68
char = U;code = 85
char = C;code = 67
char = T;code = 84
char = S;code = 83
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char = W;code = 87
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char = C;code = 67
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char = F;code = 70
char = I;code = 73
char = R;code = 82
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char = Y;code = 89
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char = C;code = 67
char = O;code = 79
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char = P;code = 80
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char = R;code = 82
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char = G;code = 71
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char = H;code = 72
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char = S;code = 83
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char = W;code = 87
char = I;code = 73
char = T;code = 84
char = H;code = 72
char = ;code = 32
char = S;code = 83
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char = N;code = 78
char = T;code = 84
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char = E;code = 69
char = T;code = 84
char = I;code = 73
char = C;code = 67
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char = S;code = 83
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char = A;code = 65
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char = D;code = 68
char = A;code = 65
char = R;code = 82
char = D;code = 68
char = S;code = 83
char = :;code = 58
char = ;code = 32
char = <;code = 60
char = /;code = 47
char = b;code = 98
char = >;code = 62
char = ;code = 32
char = N;code = 78
char = (;code = 40
char = 6;code = 54
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char = -;code = 45
char = [;code = 91
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char = b;code = 98
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char = b;code = 98
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char = l;code = 108
char = y;code = 121
char = s;code = 115
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char = n;code = 110
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char = (;code = 40
char = B;code = 66
char = I;code = 73
char = T;code = 84
char = C;code = 67
char = -;code = 45
char = L;code = 76
char = y;code = 121
char = s;code = 115
char = );code = 41
char = ,;code = 44
char = ;code = 32
char = N;code = 78
char = (;code = 40
char = 6;code = 54
char = );code = 41
char = -;code = 45
char = {;code = 123
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char = (;code = 40
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char = p;code = 112
char = h;code = 104
char = e;code = 101
char = n;code = 110
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char = l;code = 108
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char = S;code = 83
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char = l;code = 108
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char = A;code = 65
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char = T;code = 84
char = C;code = 67
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char = L;code = 76
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char = .;code = 46
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char = s;code = 115
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char = s;code = 115
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char = I;code = 73
char = T;code = 84
char = C;code = 67
char = -;code = 45
char = [;code = 91
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char = 1;code = 49
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char = );code = 41
char = (;code = 40
char = 1;code = 49
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char = );code = 41
char = N;code = 78
char = (;code = 40
char = 2;code = 50
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char = N;code = 78
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char = c;code = 99
char = e;code = 101
char = t;code = 116
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result sql = Isothiocyanates (ITCs) found in cruciferous vegetables have demonstrated cancer preventive activity in animals, and increased dietary intake of ITCs has been shown to be associated with a reduced cancer risk in humans. ITCs exert their cancer chemopreventive action by multiple mechanisms, for example, by modulating the activities of phase I and phase II drug metabolism enzymes, by inhibiting the cell cycle and histone deacetylase, and by causing apoptotic cell death. In cells, protein adducts account for most of total cellular ITC uptake at 4 h after treatment. The time course of this protein binding correlates well with the inhibition of proliferation and the induction of apoptosis. Animal studies have shown that glutathione conjugates are the major products of ITCs. The major urinary excretion products of ITCs in human are N-acetyl cysteine conjugates. Urinary metabolites might provide the exposure history of the last 24 h, if the urine of the full next day is collected. However, this is not feasible in large epidemiological studies. Furthermore, the mercapturic acids of ITC are not stable. Therefore, stable biomarkers are needed that reflect a larger time span of the ITC exposure history. We developed a method to determine stable (not cysteine adducts) reaction products of ITCs with albumin and hemoglobin in humans and mice. WE REACTED ALBUMIN WITH THE ITCS: benzyl isothiocyanate (BITC), phenylethyl isothiocyanate (PEITC), sulforaphane (SFN), and allyl isothiocyanate (AITC). After enzymatic digestion, we found one major product with lysine using LC-MS/MS.

THE IDENTITY OF THE ADDUCTS WAS CONFIRMED BY COMPARING THE ANALYSES WITH SYNTHETIC STANDARDS: N(6)-[(benzylamino)carbonothioyl]lysine (BITC-Lys), N(6)-{[(2-phenylethyl)amino]carbonothioyl}lysine (PEITC-Lys), N(6)-({[3-(methylsulfinyl)propyl]amino}carbonothioyl)lysine (SFN-Lys), and N(6)-[(allylamino]carbonothioyl]lysine (AITC-Lys). The adduct levels were quantified by isotope dilution mass spectrometry using the corresponding new ITC-[(13)C(6)(15)N(2)]lysines as internal standards. The applicability of the method was tested for biological samples obtained from different experiments. In humans consuming garden cress, watercress, and broccoli and/or in mice exposed chronically to N-acetyl-S-{[(2-phenylethyl)amino]carbonothioyl}-l-cysteine, albumin and hemoglobin adducts were found. BITC-Lys, PEITC-Lys, and SFN-Lys released after enzymatic digestion of the proteins were quantified with LC-MS/MS. This new method will enable quantification of ITC adducts in blood proteins from large prospective studies about diet and cancer. Protein adducts are involved in the chemopreventive effects of ITCs. Therefore, blood protein adducts are a potential surrogate marker for the effects of ITCs at the cellular level. This new technique will improve the assessment of ITC exposure and the power of studies on the relationship between ITC intake and cancer.

Publication: Chem. Res. Toxicol. 2010 Apr 19 ;23(4)::756-65. :doi: 10.1021/tx900393t.
Publication Date: 2010 Apr 19
Study Author(s): Kumar, Anoop;Sabbioni, Gabriele;
Institution: Department of Environmental Health Sciences, School of Public Health and Tropical Medicine, Tulane University, 1440 Canal Street, Suite 2100 (SL-29), New Orleans, Louisiana 70112, USA.
Shortcut link to this study:
Isothiocyanates (ITCs) found in cruciferous vegetables have demonstrated cancer preventive activity in animals, and increased dietary intake of ITCs has been shown to be associated with a reduced cancer risk in humans. ITCs exert their cancer chemopreventive action by multiple mechanisms, for example, by modulating the activities of phase I and phase II drug metabolism enzymes, by inhibiting the cell cycle and histone deacetylase, and by causing apoptotic cell death. In cells, protein adducts account for most of total cellular ITC uptake at 4 h after treatment. The time course of this protein binding correlates well with the inhibition of proliferation and the induction of apoptosis. Animal studies have shown that glutathione conjugates are the major products of ITCs. The major urinary excretion products of ITCs in human are N-acetyl cysteine conjugates. Urinary metabolites might provide the exposure history of the last 24 h, if the urine of the full next day is collected. However, this is not feasible in large epidemiological studies. Furthermore, the mercapturic acids of ITC are not stable. Therefore, stable biomarkers are needed that reflect a larger time span of the ITC exposure history. We developed a method to determine stable (not cysteine adducts) reaction products of ITCs with albumin and hemoglobin in humans and mice. WE REACTED ALBUMIN WITH THE ITCS: benzyl isothiocyanate (BITC), phenylethyl isothiocyanate (PEITC), sulforaphane (SFN), and allyl isothiocyanate (AITC). After enzymatic digestion, we found one major product with lysine using LC-MS/MS.

THE IDENTITY OF THE ADDUCTS WAS CONFIRMED BY COMPARING THE ANALYSES WITH SYNTHETIC STANDARDS: N(6)-[(benzylamino)carbonothioyl]lysine (BITC-Lys), N(6)-{[(2-phenylethyl)amino]carbonothioyl}lysine (PEITC-Lys), N(6)-({[3-(methylsulfinyl)propyl]amino}carbonothioyl)lysine (SFN-Lys), and N(6)-[(allylamino]carbonothioyl]lysine (AITC-Lys). The adduct levels were quantified by isotope dilution mass spectrometry using the corresponding new ITC-[(13)C(6)(15)N(2)]lysines as internal standards. The applicability of the method was tested for biological samples obtained from different experiments. In humans consuming garden cress, watercress, and broccoli and/or in mice exposed chronically to N-acetyl-S-{[(2-phenylethyl)amino]carbonothioyl}-l-cysteine, albumin and hemoglobin adducts were found. BITC-Lys, PEITC-Lys, and SFN-Lys released after enzymatic digestion of the proteins were quantified with LC-MS/MS. This new method will enable quantification of ITC adducts in blood proteins from large prospective studies about diet and cancer. Protein adducts are involved in the chemopreventive effects of ITCs. Therefore, blood protein adducts are a potential surrogate marker for the effects of ITCs at the cellular level. This new technique will improve the assessment of ITC exposure and the power of studies on the relationship between ITC intake and cancer.
PMID: 20131755

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