char = M;code = 77 char = e;code = 101 char = c;code = 99 char = h;code = 104 char = a;code = 97 char = n;code = 110 char = i;code = 105 char = s;code = 115 char = m;code = 109 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 = d;code = 100 char = i;code = 105 char = f;code = 102 char = f;code = 102 char = e;code = 101 char = r;code = 114 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = ;code = 32 char = D;code = 68 char = N;code = 78 char = A;code = 65 char = ;code = 32 char = a;code = 97 char = d;code = 100 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = t;code = 116 char = ;code = 32 char = f;code = 102 char = o;code = 111 char = r;code = 114 char = m;code = 109 char = i;code = 105 char = n;code = 110 char = g;code = 103 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 = 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 = u;code = 117 char = r;code = 114 char = b;code = 98 char = a;code = 97 char = n;code = 110 char = ;code = 32 char = a;code = 97 char = i;code = 105 char = r;code = 114 char = ;code = 32 char = p;code = 112 char = o;code = 111 char = l;code = 108 char = l;code = 108 char = u;code = 117 char = t;code = 116 char = a;code = 97 char = n;code = 110 char = t;code = 116 char = s;code = 115 char = ;code = 32 char = 2;code = 50 char = -;code = 45 char = n;code = 110 char = i;code = 105 char = t;code = 116 char = r;code = 114 char = o;code = 111 char = b;code = 98 char = e;code = 101 char = n;code = 110 char = z;code = 122 char = a;code = 97 char = n;code = 110 char = t;code = 116 char = h;code = 104 char = r;code = 114 char = o;code = 111 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 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 = g;code = 103 char = e;code = 101 char = n;code = 110 char = i;code = 105 char = c;code = 99 char = ;code = 32 char = 3;code = 51 char = -;code = 45 char = n;code = 110 char = i;code = 105 char = t;code = 116 char = r;code = 114 char = o;code = 111 char = b;code = 98 char = e;code = 101 char = n;code = 110 char = z;code = 122 char = a;code = 97 char = n;code = 110 char = t;code = 116 char = h;code = 104 char = r;code = 114 char = o;code = 111 char = n;code = 110 char = e;code = 101 char = .;code = 46 result sql = Mechanisms of the different DNA adduct forming potentials of the urban air pollutants 2-nitrobenzanthrone and carcinogenic 3-nitrobenzanthrone.
Mechanisms of the different DNA adduct forming potentials of the urban air pollutants 2-nitrobenzanthrone and carcinogenic 3-nitrobenzanthrone.char = 2;code = 50 char = -;code = 45 char = N;code = 78 char = i;code = 105 char = t;code = 116 char = r;code = 114 char = o;code = 111 char = b;code = 98 char = e;code = 101 char = n;code = 110 char = z;code = 122 char = a;code = 97 char = n;code = 110 char = t;code = 116 char = h;code = 104 char = r;code = 114 char = o;code = 111 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = (;code = 40 char = 2;code = 50 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = );code = 41 char = ;code = 32 char = h;code = 104 char = a;code = 97 char = s;code = 115 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = c;code = 99 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = l;code = 108 char = y;code = 121 char = ;code = 32 char = b;code = 98 char = e;code = 101 char = e;code = 101 char = n;code = 110 char = ;code = 32 char = d;code = 100 char = e;code = 101 char = t;code = 116 char = e;code = 101 char = c;code = 99 char = t;code = 116 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = a;code = 97 char = m;code = 109 char = b;code = 98 char = i;code = 105 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = ;code = 32 char = a;code = 97 char = i;code = 105 char = r;code = 114 char = ;code = 32 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = t;code = 116 char = i;code = 105 char = c;code = 99 char = u;code = 117 char = l;code = 108 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = ;code = 32 char = m;code = 109 char = a;code = 97 char = t;code = 116 char = t;code = 116 char = e;code = 101 char = r;code = 114 char = .;code = 46 char = ;code = 32 char = I;code = 73 char = t;code = 116 char = s;code = 115 char = ;code = 32 char = i;code = 105 char = s;code = 115 char = o;code = 111 char = m;code = 109 char = e;code = 101 char = r;code = 114 char = ;code = 32 char = 3;code = 51 char = -;code = 45 char = n;code = 110 char = i;code = 105 char = t;code = 116 char = r;code = 114 char = o;code = 111 char = b;code = 98 char = e;code = 101 char = n;code = 110 char = z;code = 122 char = a;code = 97 char = n;code = 110 char = t;code = 116 char = h;code = 104 char = r;code = 114 char = o;code = 111 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = (;code = 40 char = 3;code = 51 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = );code = 41 char = ;code = 32 char = i;code = 105 char = s;code = 115 char = ;code = 32 char = a;code = 97 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 = ;code = 32 char = m;code = 109 char = u;code = 117 char = t;code = 116 char = a;code = 97 char = g;code = 103 char = e;code = 101 char = n;code = 110 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = s;code = 115 char = u;code = 117 char = s;code = 115 char = p;code = 112 char = e;code = 101 char = c;code = 99 char = t;code = 116 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = h;code = 104 char = u;code = 117 char = m;code = 109 char = a;code = 97 char = n;code = 110 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 = g;code = 103 char = e;code = 101 char = n;code = 110 char = ;code = 32 char = i;code = 105 char = d;code = 100 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = i;code = 105 char = f;code = 102 char = i;code = 105 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = d;code = 100 char = i;code = 105 char = e;code = 101 char = s;code = 115 char = e;code = 101 char = l;code = 108 char = ;code = 32 char = e;code = 101 char = x;code = 120 char = h;code = 104 char = a;code = 97 char = u;code = 117 char = s;code = 115 char = t;code = 116 char = .;code = 46 char = ;code = 32 char = W;code = 87 char = e;code = 101 char = ;code = 32 char = c;code = 99 char = o;code = 111 char = m;code = 109 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 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 = c;code = 99 char = i;code = 105 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = h;code = 104 char = u;code = 117 char = m;code = 109 char = a;code = 97 char = n;code = 110 char = ;code = 32 char = e;code = 101 char = n;code = 110 char = z;code = 122 char = y;code = 121 char = m;code = 109 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = c;code = 99 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 = s;code = 115 char = ;code = 32 char = [;code = 91 char = h;code = 104 char = e;code = 101 char = p;code = 112 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = c;code = 99 char = ;code = 32 char = m;code = 109 char = i;code = 105 char = c;code = 99 char = r;code = 114 char = o;code = 111 char = s;code = 115 char = o;code = 111 char = m;code = 109 char = e;code = 101 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 = s;code = 115 char = o;code = 111 char = l;code = 108 char = s;code = 115 char = ,;code = 44 char = ;code = 32 char = N;code = 78 char = A;code = 65 char = D;code = 68 char = (;code = 40 char = P;code = 80 char = );code = 41 char = H;code = 72 char = :;code = 58 char = q;code = 113 char = u;code = 117 char = i;code = 105 char = n;code = 110 char = o;code = 111 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = o;code = 111 char = x;code = 120 char = i;code = 105 char = d;code = 100 char = o;code = 111 char = r;code = 114 char = e;code = 101 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = t;code = 116 char = a;code = 97 char = s;code = 115 char = e;code = 101 char = ;code = 32 char = 1;code = 49 char = ;code = 32 char = (;code = 40 char = N;code = 78 char = Q;code = 81 char = O;code = 79 char = 1;code = 49 char = );code = 41 char = ,;code = 44 char = ;code = 32 char = x;code = 120 char = a;code = 97 char = n;code = 110 char = t;code = 116 char = h;code = 104 char = i;code = 105 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = o;code = 111 char = x;code = 120 char = i;code = 105 char = d;code = 100 char = a;code = 97 char = s;code = 115 char = e;code = 101 char = ,;code = 44 char = ;code = 32 char = <;code = 60 char = b;code = 98 char = >;code = 62 char = N;code = 78 char = A;code = 65 char = D;code = 68 char = P;code = 80 char = H;code = 72 char = :;code = 58 char = ;code = 32 char = <;code = 60 char = /;code = 47 char = b;code = 98 char = >;code = 62 char = c;code = 99 char = y;code = 121 char = t;code = 116 char = o;code = 111 char = c;code = 99 char = h;code = 104 char = r;code = 114 char = o;code = 111 char = m;code = 109 char = e;code = 101 char = ;code = 32 char = P;code = 80 char = 4;code = 52 char = 5;code = 53 char = 0;code = 48 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = t;code = 116 char = a;code = 97 char = s;code = 115 char = e;code = 101 char = ,;code = 44 char = ;code = 32 char = N;code = 78 char = ,;code = 44 char = O;code = 79 char = -;code = 45 char = a;code = 97 char = c;code = 99 char = e;code = 101 char = t;code = 116 char = y;code = 121 char = l;code = 108 char = t;code = 116 char = r;code = 114 char = a;code = 97 char = n;code = 110 char = s;code = 115 char = f;code = 102 char = e;code = 101 char = r;code = 114 char = a;code = 97 char = s;code = 115 char = e;code = 101 char = s;code = 115 char = ,;code = 44 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = s;code = 115 char = u;code = 117 char = l;code = 108 char = f;code = 102 char = o;code = 111 char = t;code = 116 char = r;code = 114 char = a;code = 97 char = n;code = 110 char = s;code = 115 char = f;code = 102 char = e;code = 101 char = r;code = 114 char = a;code = 97 char = s;code = 115 char = e;code = 101 char = s;code = 115 char = ];code = 93 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = h;code = 104 char = u;code = 117 char = m;code = 109 char = a;code = 97 char = n;code = 110 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = i;code = 105 char = m;code = 109 char = a;code = 97 char = r;code = 114 char = y;code = 121 char = ;code = 32 char = h;code = 104 char = e;code = 101 char = p;code = 112 char = a;code = 97 char = t;code = 116 char = o;code = 111 char = c;code = 99 char = y;code = 121 char = t;code = 116 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = a;code = 97 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = v;code = 118 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = ;code = 32 char = 2;code = 50 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = i;code = 105 char = t;code = 116 char = s;code = 115 char = ;code = 32 char = i;code = 105 char = s;code = 115 char = o;code = 111 char = m;code = 109 char = e;code = 101 char = r;code = 114 char = ;code = 32 char = 3;code = 51 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = ;code = 32 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = s;code = 115 char = p;code = 112 char = e;code = 101 char = c;code = 99 char = i;code = 105 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = f;code = 102 char = o;code = 111 char = r;code = 114 char = m;code = 109 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = D;code = 68 char = N;code = 78 char = A;code = 65 char = ;code = 32 char = a;code = 97 char = d;code = 100 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = t;code = 116 char = s;code = 115 char = .;code = 46 char = ;code = 32 char = I;code = 73 char = n;code = 110 char = ;code = 32 char = c;code = 99 char = o;code = 111 char = n;code = 110 char = t;code = 116 char = r;code = 114 char = a;code = 97 char = s;code = 115 char = t;code = 116 char = ;code = 32 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = 3;code = 51 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = ,;code = 44 char = ;code = 32 char = 2;code = 50 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = ;code = 32 char = w;code = 119 char = a;code = 97 char = s;code = 115 char = ;code = 32 char = n;code = 110 char = o;code = 111 char = t;code = 116 char = ;code = 32 char = m;code = 109 char = e;code = 101 char = t;code = 116 char = a;code = 97 char = b;code = 98 char = o;code = 111 char = l;code = 108 char = i;code = 105 char = z;code = 122 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = a;code = 97 char = t;code = 116 char = ;code = 32 char = d;code = 100 char = e;code = 101 char = t;code = 116 char = e;code = 101 char = c;code = 99 char = t;code = 116 char = a;code = 97 char = b;code = 98 char = l;code = 108 char = e;code = 101 char = ;code = 32 char = l;code = 108 char = e;code = 101 char = v;code = 118 char = e;code = 101 char = l;code = 108 char = s;code = 115 char = ;code = 32 char = b;code = 98 char = y;code = 121 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = t;code = 116 char = e;code = 101 char = s;code = 115 char = t;code = 116 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = h;code = 104 char = u;code = 117 char = m;code = 109 char = a;code = 97 char = n;code = 110 char = ;code = 32 char = e;code = 101 char = n;code = 110 char = z;code = 122 char = y;code = 121 char = m;code = 109 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = c;code = 99 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 = s;code = 115 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = e;code = 101 char = n;code = 110 char = z;code = 122 char = y;code = 121 char = m;code = 109 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = e;code = 101 char = x;code = 120 char = p;code = 112 char = r;code = 114 char = e;code = 101 char = s;code = 115 char = s;code = 115 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = h;code = 104 char = u;code = 117 char = m;code = 109 char = a;code = 97 char = n;code = 110 char = ;code = 32 char = h;code = 104 char = e;code = 101 char = p;code = 112 char = a;code = 97 char = t;code = 116 char = o;code = 111 char = c;code = 99 char = y;code = 121 char = t;code = 116 char = e;code = 101 char = s;code = 115 char = ,;code = 44 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = n;code = 110 char = o;code = 111 char = ;code = 32 char = D;code = 68 char = N;code = 78 char = A;code = 65 char = ;code = 32 char = a;code = 97 char = d;code = 100 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = t;code = 116 char = s;code = 115 char = ;code = 32 char = d;code = 100 char = e;code = 101 char = t;code = 116 char = e;code = 101 char = c;code = 99 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 = y;code = 121 char = ;code = 32 char = (;code = 40 char = 3;code = 51 char = 2;code = 50 char = );code = 41 char = P;code = 80 char = -;code = 45 char = p;code = 112 char = o;code = 111 char = s;code = 115 char = t;code = 116 char = l;code = 108 char = a;code = 97 char = b;code = 98 char = e;code = 101 char = l;code = 108 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = w;code = 119 char = e;code = 101 char = r;code = 114 char = e;code = 101 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 = e;code = 101 char = d;code = 100 char = ;code = 32 char = b;code = 98 char = y;code = 121 char = ;code = 32 char = 2;code = 50 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = .;code = 46 char = ;code = 32 char = E;code = 69 char = v;code = 118 char = e;code = 101 char = n;code = 110 char = ;code = 32 char = N;code = 78 char = Q;code = 81 char = O;code = 79 char = 1;code = 49 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 = o;code = 111 char = s;code = 115 char = t;code = 116 char = ;code = 32 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 = ;code = 32 char = h;code = 104 char = u;code = 117 char = m;code = 109 char = a;code = 97 char = n;code = 110 char = ;code = 32 char = e;code = 101 char = n;code = 110 char = z;code = 122 char = y;code = 121 char = m;code = 109 char = e;code = 101 char = ;code = 32 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = b;code = 98 char = i;code = 105 char = o;code = 111 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 = 3;code = 51 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = ,;code = 44 char = ;code = 32 char = d;code = 100 char = i;code = 105 char = d;code = 100 char = ;code = 32 char = n;code = 110 char = o;code = 111 char = t;code = 116 char = ;code = 32 char = a;code = 97 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = v;code = 118 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = ;code = 32 char = 2;code = 50 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = .;code = 46 char = ;code = 32 char = M;code = 77 char = o;code = 111 char = l;code = 108 char = e;code = 101 char = c;code = 99 char = u;code = 117 char = l;code = 108 char = a;code = 97 char = r;code = 114 char = ;code = 32 char = d;code = 100 char = o;code = 111 char = c;code = 99 char = k;code = 107 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = 2;code = 50 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = 3;code = 51 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 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 = ;code = 32 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 = s;code = 115 char = i;code = 105 char = t;code = 116 char = e;code = 101 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = N;code = 78 char = Q;code = 81 char = O;code = 79 char = 1;code = 49 char = ;code = 32 char = s;code = 115 char = h;code = 104 char = o;code = 111 char = w;code = 119 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = s;code = 115 char = i;code = 105 char = m;code = 109 char = i;code = 105 char = l;code = 108 char = a;code = 97 char = r;code = 114 char = ;code = 32 char = b;code = 98 char = i;code = 105 char = n;code = 110 char = d;code = 100 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = a;code = 97 char = f;code = 102 char = f;code = 102 char = i;code = 105 char = n;code = 110 char = i;code = 105 char = t;code = 116 char = i;code = 105 char = e;code = 101 char = s;code = 115 char = ;;code = 59 char = ;code = 32 char = h;code = 104 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 = e;code = 101 char = ;code = 32 char = b;code = 98 char = i;code = 105 char = n;code = 110 char = d;code = 100 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = o;code = 111 char = r;code = 114 char = i;code = 105 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = 2;code = 50 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = ;code = 32 char = d;code = 100 char = o;code = 111 char = e;code = 101 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 = a;code = 97 char = v;code = 118 char = o;code = 111 char = r;code = 114 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = o;code = 111 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 = n;code = 110 char = i;code = 105 char = t;code = 116 char = r;code = 114 char = o;code = 111 char = ;code = 32 char = g;code = 103 char = r;code = 114 char = o;code = 111 char = u;code = 117 char = p;code = 112 char = .;code = 46 char = ;code = 32 char = T;code = 84 char = h;code = 104 char = i;code = 105 char = s;code = 115 char = ;code = 32 char = w;code = 119 char = a;code = 97 char = s;code = 115 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = l;code = 108 char = i;code = 105 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = w;code = 119 char = i;code = 105 char = t;code = 116 char = h;code = 104 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 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 = o;code = 111 char = n;code = 110 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = 3;code = 51 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = -;code = 45 char = D;code = 68 char = N;code = 78 char = A;code = 65 char = ;code = 32 char = a;code = 97 char = d;code = 100 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = t;code = 116 char = ;code = 32 char = f;code = 102 char = o;code = 111 char = r;code = 114 char = m;code = 109 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = b;code = 98 char = y;code = 121 char = ;code = 32 char = 2;code = 50 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = ,;code = 44 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 = 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 = 2;code = 50 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = ;code = 32 char = c;code = 99 char = a;code = 97 char = n;code = 110 char = ;code = 32 char = c;code = 99 char = o;code = 111 char = m;code = 109 char = p;code = 112 char = e;code = 101 char = t;code = 116 char = e;code = 101 char = ;code = 32 char = w;code = 119 char = i;code = 105 char = t;code = 116 char = h;code = 104 char = ;code = 32 char = 3;code = 51 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = ;code = 32 char = f;code = 102 char = o;code = 111 char = r;code = 114 char = ;code = 32 char = b;code = 98 char = i;code = 105 char = n;code = 110 char = d;code = 100 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = N;code = 78 char = Q;code = 81 char = O;code = 79 char = 1;code = 49 char = ,;code = 44 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = r;code = 114 char = e;code = 101 char = b;code = 98 char = y;code = 121 char = ;code = 32 char = d;code = 100 char = e;code = 101 char = c;code = 99 char = r;code = 114 char = e;code = 101 char = a;code = 97 char = s;code = 115 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 char = ;code = 32 char = m;code = 109 char = e;code = 101 char = t;code = 116 char = a;code = 97 char = b;code = 98 char = o;code = 111 char = l;code = 108 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 = a;code = 97 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = 3;code = 51 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = .;code = 46 char = ;code = 32 char = I;code = 73 char = n;code = 110 char = ;code = 32 char = a;code = 97 char = d;code = 100 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 = ,;code = 44 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = e;code = 101 char = d;code = 100 char = i;code = 105 char = c;code = 99 char = t;code = 116 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = e;code = 101 char = q;code = 113 char = u;code = 117 char = i;code = 105 char = l;code = 108 char = i;code = 105 char = b;code = 98 char = r;code = 114 char = i;code = 105 char = u;code = 117 char = m;code = 109 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 = f;code = 102 char = a;code = 97 char = v;code = 118 char = o;code = 111 char = r;code = 114 char = ;code = 32 char = a;code = 97 char = ;code = 32 char = 3;code = 51 char = ;code = 32 char = o;code = 111 char = r;code = 114 char = d;code = 100 char = e;code = 101 char = r;code = 114 char = s;code = 115 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = m;code = 109 char = a;code = 97 char = g;code = 103 char = n;code = 110 char = i;code = 105 char = t;code = 116 char = u;code = 117 char = d;code = 100 char = e;code = 101 char = ;code = 32 char = h;code = 104 char = i;code = 105 char = g;code = 103 char = h;code = 104 char = e;code = 101 char = r;code = 114 char = ;code = 32 char = d;code = 100 char = i;code = 105 char = s;code = 115 char = s;code = 115 char = o;code = 111 char = c;code = 99 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 = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = N;code = 78 char = -;code = 45 char = O;code = 79 char = H;code = 72 char = -;code = 45 char = 3;code = 51 char = -;code = 45 char = A;code = 65 char = B;code = 66 char = A;code = 65 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = c;code = 99 char = o;code = 111 char = m;code = 109 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = i;code = 105 char = s;code = 115 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = N;code = 78 char = -;code = 45 char = O;code = 79 char = H;code = 72 char = -;code = 45 char = 2;code = 50 char = -;code = 45 char = A;code = 65 char = B;code = 66 char = A;code = 65 char = .;code = 46 char = ;code = 32 char = T;code = 84 char = h;code = 104 char = e;code = 101 char = s;code = 115 char = e;code = 101 char = ;code = 32 char = f;code = 102 char = i;code = 105 char = n;code = 110 char = d;code = 100 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = s;code = 115 char = ;code = 32 char = e;code = 101 char = x;code = 120 char = p;code = 112 char = l;code = 108 char = a;code = 97 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = v;code = 118 char = e;code = 101 char = r;code = 114 char = y;code = 121 char = ;code = 32 char = d;code = 100 char = i;code = 105 char = f;code = 102 char = f;code = 102 char = e;code = 101 char = r;code = 114 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = ;code = 32 char = g;code = 103 char = e;code = 101 char = n;code = 110 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 = 44 char = ;code = 32 char = m;code = 109 char = u;code = 117 char = t;code = 116 char = a;code = 97 char = g;code = 103 char = e;code = 101 char = n;code = 110 char = i;code = 105 char = c;code = 99 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 = D;code = 68 char = N;code = 78 char = A;code = 65 char = ;code = 32 char = a;code = 97 char = d;code = 100 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = t;code = 116 char = ;code = 32 char = f;code = 102 char = o;code = 111 char = r;code = 114 char = m;code = 109 char = i;code = 105 char = n;code = 110 char = g;code = 103 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 = 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 = t;code = 116 char = w;code = 119 char = o;code = 111 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 char = ;code = 32 char = C;code = 67 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 = i;code = 105 char = v;code = 118 char = e;code = 101 char = l;code = 108 char = y;code = 121 char = ,;code = 44 char = ;code = 32 char = o;code = 111 char = u;code = 117 char = r;code = 114 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = s;code = 115 char = u;code = 117 char = l;code = 108 char = t;code = 116 char = s;code = 115 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 = ;code = 32 char = t;code = 116 char = h;code = 104 char = a;code = 97 char = t;code = 116 char = ;code = 32 char = 2;code = 50 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = ;code = 32 char = p;code = 112 char = o;code = 111 char = s;code = 115 char = s;code = 115 char = e;code = 101 char = s;code = 115 char = s;code = 115 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = a;code = 97 char = ;code = 32 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 = v;code = 118 char = e;code = 101 char = l;code = 108 char = y;code = 121 char = ;code = 32 char = l;code = 108 char = o;code = 111 char = w;code = 119 char = e;code = 101 char = r;code = 114 char = ;code = 32 char = r;code = 114 char = i;code = 105 char = s;code = 115 char = k;code = 107 char = ;code = 32 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = h;code = 104 char = u;code = 117 char = m;code = 109 char = a;code = 97 char = n;code = 110 char = s;code = 115 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = a;code = 97 char = n;code = 110 char = ;code = 32 char = 3;code = 51 char = -;code = 45 char = N;code = 78 char = B;code = 66 char = A;code = 65 char = .;code = 46 char = <;code = 60 char = b;code = 98 char = r;code = 114 char = /;code = 47 char = >;code = 62 result sql = 2-Nitrobenzanthrone (2-NBA) has recently been detected in ambient air particulate matter. Its isomer 3-nitrobenzanthrone (3-NBA) is a potent mutagen and suspected human carcinogen identified in diesel exhaust. We compared the efficiencies of human enzymatic systems [hepatic microsomes and cytosols, NAD(P)H:quinone oxidoreductase 1 (NQO1), xanthine oxidase, NADPH: cytochrome P450 reductase, N,O-acetyltransferases, and sulfotransferases] and human primary hepatocytes to activate 2-NBA and its isomer 3-NBA to species forming DNA adducts. In contrast to 3-NBA, 2-NBA was not metabolized at detectable levels by the tested human enzymatic systems and enzymes expressed in human hepatocytes, and no DNA adducts detectable by (32)P-postlabeling were generated by 2-NBA. Even NQO1, the most efficient human enzyme to bioactive 3-NBA, did not activate 2-NBA. Molecular docking of 2-NBA and 3-NBA to the active site of NQO1 showed similar binding affinities; however, the binding orientation of 2-NBA does not favor the reduction of the nitro group. This was in line with the inhibition of 3-NBA-DNA adduct formation by 2-NBA, indicating that 2-NBA can compete with 3-NBA for binding to NQO1, thereby decreasing the metabolic activation of 3-NBA. In addition, the predicted equilibrium conditions favor a 3 orders of magnitude higher dissociation of N-OH-3-ABA in comparison to N-OH-2-ABA. These findings explain the very different genotoxicity, mutagenicity, and DNA adduct forming potential of the two compounds. Collectively, our results suggest that 2-NBA possesses a relatively lower risk to humans than 3-NBA.
Publication: Chem. Res. Toxicol. 2010 Jul 19 ;23(7)::1192-201. :doi: 10.1021/tx100052d.
Publication Date: 2010 Jul 19
Study Author(s): Stiborová, Marie;Martínek, Václav;Svobodová, Martina;Sístková, Jana;Dvorák, Zdenek;Ulrichová, Jitka;Simánek, Vilím;Frei, Eva;Schmeiser, Heinz H;Phillips, David H;Arlt, Volker M;
Institution: Department of Biochemistry, Faculty of Science, Charles University, Albertov 2030, Prague 2, Czech Republic.
[email protected]
Shortcut link to this study:
2-Nitrobenzanthrone (2-NBA) has recently been detected in ambient air particulate matter. Its isomer 3-nitrobenzanthrone (3-NBA) is a potent mutagen and suspected human carcinogen identified in diesel exhaust. We compared the efficiencies of human enzymatic systems [hepatic microsomes and cytosols, NAD(P)H:quinone oxidoreductase 1 (NQO1), xanthine oxidase, NADPH: cytochrome P450 reductase, N,O-acetyltransferases, and sulfotransferases] and human primary hepatocytes to activate 2-NBA and its isomer 3-NBA to species forming DNA adducts. In contrast to 3-NBA, 2-NBA was not metabolized at detectable levels by the tested human enzymatic systems and enzymes expressed in human hepatocytes, and no DNA adducts detectable by (32)P-postlabeling were generated by 2-NBA. Even NQO1, the most efficient human enzyme to bioactive 3-NBA, did not activate 2-NBA. Molecular docking of 2-NBA and 3-NBA to the active site of NQO1 showed similar binding affinities; however, the binding orientation of 2-NBA does not favor the reduction of the nitro group. This was in line with the inhibition of 3-NBA-DNA adduct formation by 2-NBA, indicating that 2-NBA can compete with 3-NBA for binding to NQO1, thereby decreasing the metabolic activation of 3-NBA. In addition, the predicted equilibrium conditions favor a 3 orders of magnitude higher dissociation of N-OH-3-ABA in comparison to N-OH-2-ABA. These findings explain the very different genotoxicity, mutagenicity, and DNA adduct forming potential of the two compounds. Collectively, our results suggest that 2-NBA possesses a relatively lower risk to humans than 3-NBA.
PMID: 20545351