char = R;code = 82 char = e;code = 101 char = v;code = 118 char = e;code = 101 char = r;code = 114 char = s;code = 115 char = i;code = 105 char = b;code = 98 char = i;code = 105 char = l;code = 108 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 = c;code = 99 char = o;code = 111 char = v;code = 118 char = a;code = 97 char = l;code = 108 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = ;code = 32 char = e;code = 101 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 = p;code = 112 char = h;code = 104 char = i;code = 105 char = l;code = 108 char = e;code = 101 char = -;code = 45 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = t;code = 116 char = e;code = 101 char = i;code = 105 char = n;code = 110 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 = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = c;code = 99 char = h;code = 104 char = e;code = 101 char = m;code = 109 char = i;code = 105 char = c;code = 99 char = a;code = 97 char = l;code = 108 char = ;code = 32 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 = 46 result sql = Reversibility of covalent electrophile-protein adducts and chemical toxicity.
Reversibility of covalent electrophile-protein adducts and chemical toxicity.char = T;code = 84 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = b;code = 98 char = i;code = 105 char = o;code = 111 char = t;code = 116 char = i;code = 105 char = n;code = 110 char = -;code = 45 char = t;code = 116 char = a;code = 97 char = g;code = 103 char = g;code = 103 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = e;code = 101 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 = p;code = 112 char = h;code = 104 char = i;code = 105 char = l;code = 108 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = 1;code = 49 char = -;code = 45 char = b;code = 98 char = i;code = 105 char = o;code = 111 char = t;code = 116 char = i;code = 105 char = n;code = 110 char = a;code = 97 char = m;code = 109 char = i;code = 105 char = d;code = 100 char = o;code = 111 char = -;code = 45 char = 4;code = 52 char = -;code = 45 char = (;code = 40 char = 4;code = 52 char = ';code = 39 char = -;code = 45 char = [;code = 91 char = m;code = 109 char = a;code = 97 char = l;code = 108 char = e;code = 101 char = i;code = 105 char = m;code = 109 char = i;code = 105 char = d;code = 100 char = o;code = 111 char = e;code = 101 char = t;code = 116 char = h;code = 104 char = y;code = 121 char = l;code = 108 char = c;code = 99 char = y;code = 121 char = c;code = 99 char = l;code = 108 char = o;code = 111 char = h;code = 104 char = e;code = 101 char = x;code = 120 char = a;code = 97 char = n;code = 110 char = e;code = 101 char = ];code = 93 char = -;code = 45 char = c;code = 99 char = a;code = 97 char = r;code = 114 char = b;code = 98 char = o;code = 111 char = x;code = 120 char = a;code = 97 char = m;code = 109 char = i;code = 105 char = d;code = 100 char = o;code = 111 char = );code = 41 char = b;code = 98 char = u;code = 117 char = t;code = 116 char = a;code = 97 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = (;code = 40 char = B;code = 66 char = M;code = 77 char = C;code = 67 char = C;code = 67 char = );code = 41 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = N;code = 78 char = -;code = 45 char = i;code = 105 char = o;code = 111 char = d;code = 100 char = o;code = 111 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 = -;code = 45 char = N;code = 78 char = -;code = 45 char = b;code = 98 char = i;code = 105 char = o;code = 111 char = t;code = 116 char = i;code = 105 char = n;code = 110 char = y;code = 121 char = l;code = 108 char = h;code = 104 char = e;code = 101 char = x;code = 120 char = y;code = 121 char = l;code = 108 char = e;code = 101 char = n;code = 110 char = e;code = 101 char = d;code = 100 char = i;code = 105 char = a;code = 97 char = m;code = 109 char = i;code = 105 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = (;code = 40 char = I;code = 73 char = A;code = 65 char = B;code = 66 char = );code = 41 char = ;code = 32 char = h;code = 104 char = a;code = 97 char = v;code = 118 char = e;code = 101 char = ;code = 32 char = b;code = 98 char = e;code = 101 char = e;code = 101 char = n;code = 110 char = ;code = 32 char = u;code = 117 char = s;code = 115 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = a;code = 97 char = s;code = 115 char = ;code = 32 char = m;code = 109 char = o;code = 111 char = d;code = 100 char = e;code = 101 char = l;code = 108 char = ;code = 32 char = e;code = 101 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 = p;code = 112 char = h;code = 104 char = i;code = 105 char = l;code = 108 char = e;code = 101 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = b;code = 98 char = e;code = 101 char = s;code = 115 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 = l;code = 108 char = e;code = 101 char = x;code = 120 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = t;code = 116 char = e;code = 101 char = o;code = 111 char = m;code = 109 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = t;code = 116 char = o;code = 111 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 = y;code = 121 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = t;code = 116 char = e;code = 101 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = t;code = 116 char = a;code = 97 char = r;code = 114 char = g;code = 103 char = e;code = 101 char = t;code = 116 char = s;code = 115 char = ;code = 32 char = a;code = 97 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 = e;code = 101 char = d;code = 100 char = ;code = 32 char = w;code = 119 char = i;code = 105 char = t;code = 116 char = h;code = 104 char = ;code = 32 char = c;code = 99 char = h;code = 104 char = e;code = 101 char = m;code = 109 char = i;code = 105 char = c;code = 99 char = a;code = 97 char = l;code = 108 char = ;code = 32 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 = 46 char = ;code = 32 char = W;code = 87 char = h;code = 104 char = e;code = 101 char = r;code = 114 char = e;code = 101 char = a;code = 97 char = s;code = 115 char = ;code = 32 char = I;code = 73 char = A;code = 65 char = B;code = 66 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 = s;code = 115 char = ;code = 32 char = s;code = 115 char = t;code = 116 char = r;code = 114 char = e;code = 101 char = s;code = 115 char = s;code = 115 char = ;code = 32 char = s;code = 115 char = i;code = 105 char = g;code = 103 char = n;code = 110 char = a;code = 97 char = l;code = 108 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = a;code = 97 char = p;code = 112 char = o;code = 111 char = p;code = 112 char = t;code = 116 char = o;code = 111 char = s;code = 115 char = i;code = 105 char = s;code = 115 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = H;code = 72 char = E;code = 69 char = K;code = 75 char = 2;code = 50 char = 9;code = 57 char = 3;code = 51 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 = 44 char = ;code = 32 char = B;code = 66 char = M;code = 77 char = C;code = 67 char = C;code = 67 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 = 46 char = ;code = 32 char = C;code = 67 char = y;code = 121 char = s;code = 115 char = t;code = 116 char = e;code = 101 char = i;code = 105 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = M;code = 77 char = i;code = 105 char = c;code = 99 char = h;code = 104 char = a;code = 97 char = e;code = 101 char = l;code = 108 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 = f;code = 102 char = o;code = 111 char = r;code = 114 char = m;code = 109 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 = B;code = 66 char = M;code = 77 char = C;code = 67 char = C;code = 67 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 = n;code = 110 char = b;code = 98 char = i;code = 105 char = o;code = 111 char = t;code = 116 char = i;code = 105 char = n;code = 110 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 = a;code = 97 char = n;code = 110 char = a;code = 97 char = l;code = 108 char = o;code = 111 char = g;code = 103 char = u;code = 117 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = r;code = 114 char = a;code = 97 char = p;code = 112 char = i;code = 105 char = d;code = 100 char = l;code = 108 char = y;code = 121 char = ;code = 32 char = d;code = 100 char = i;code = 105 char = s;code = 115 char = a;code = 97 char = p;code = 112 char = p;code = 112 char = e;code = 101 char = a;code = 97 char = r;code = 114 char = e;code = 101 char = d;code = 100 char = ;code = 32 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 = i;code = 105 char = n;code = 110 char = t;code = 116 char = a;code = 97 char = c;code = 99 char = t;code = 116 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 = 44 char = ;code = 32 char = w;code = 119 char = h;code = 104 char = e;code = 101 char = r;code = 114 char = e;code = 101 char = a;code = 97 char = s;code = 115 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 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 = w;code = 119 char = e;code = 101 char = r;code = 114 char = e;code = 101 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 = i;code = 105 char = n;code = 110 char = ;code = 32 char = B;code = 66 char = M;code = 77 char = C;code = 67 char = C;code = 67 char = -;code = 45 char = t;code = 116 char = r;code = 114 char = e;code = 101 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = s;code = 115 char = u;code = 117 char = b;code = 98 char = c;code = 99 char = e;code = 101 char = l;code = 108 char = l;code = 108 char = u;code = 117 char = l;code = 108 char = a;code = 97 char = r;code = 114 char = ;code = 32 char = f;code = 102 char = r;code = 114 char = a;code = 97 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = s;code = 115 char = ,;code = 44 char = ;code = 32 char = e;code = 101 char = v;code = 118 char = e;code = 101 char = n;code = 110 char = ;code = 32 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 = p;code = 112 char = r;code = 114 char = e;code = 101 char = s;code = 115 char = e;code = 101 char = n;code = 110 char = c;code = 99 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 char = ;code = 32 char = c;code = 99 char = e;code = 101 char = l;code = 108 char = l;code = 108 char = u;code = 117 char = l;code = 108 char = a;code = 97 char = r;code = 114 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 = n;code = 110 char = t;code = 116 char = s;code = 115 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = g;code = 103 char = l;code = 108 char = u;code = 117 char = t;code = 116 char = a;code = 97 char = t;code = 116 char = h;code = 104 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = e;code = 101 char = ,;code = 44 char = ;code = 32 char = N;code = 78 char = A;code = 65 char = D;code = 68 char = H;code = 72 char = ,;code = 44 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = N;code = 78 char = A;code = 65 char = D;code = 68 char = P;code = 80 char = H;code = 72 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 = 44 char = ;code = 32 char = c;code = 99 char = y;code = 121 char = s;code = 115 char = t;code = 116 char = e;code = 101 char = i;code = 105 char = n;code = 110 char = e;code = 101 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = i;code = 105 char = o;code = 111 char = e;code = 101 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = r;code = 114 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 = f;code = 102 char = o;code = 111 char = r;code = 114 char = m;code = 109 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 = I;code = 73 char = A;code = 65 char = B;code = 66 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 = n;code = 110 char = o;code = 111 char = n;code = 110 char = b;code = 98 char = i;code = 105 char = o;code = 111 char = t;code = 116 char = i;code = 105 char = n;code = 110 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 = a;code = 97 char = n;code = 110 char = a;code = 97 char = l;code = 108 char = o;code = 111 char = g;code = 103 char = u;code = 117 char = e;code = 101 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 = t;code = 116 char = a;code = 97 char = b;code = 98 char = l;code = 108 char = e;code = 101 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = t;code = 116 char = a;code = 97 char = c;code = 99 char = t;code = 116 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 = 46 char = ;code = 32 char = L;code = 76 char = o;code = 111 char = s;code = 115 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 = B;code = 66 char = M;code = 77 char = C;code = 67 char = C;code = 67 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 = i;code = 105 char = n;code = 110 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 = r;code = 114 char = e;code = 101 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = a;code = 97 char = t;code = 116 char = ;code = 32 char = 4;code = 52 char = ;code = 32 char = d;code = 100 char = e;code = 101 char = g;code = 103 char = r;code = 114 char = e;code = 101 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = C;code = 67 char = ,;code = 44 char = ;code = 32 char = w;code = 119 char = h;code = 104 char = i;code = 105 char = c;code = 99 char = h;code = 104 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 = s;code = 115 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 = v;code = 118 char = o;code = 111 char = l;code = 108 char = v;code = 118 char = e;code = 101 char = m;code = 109 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = a;code = 97 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 = p;code = 112 char = r;code = 114 char = o;code = 111 char = c;code = 99 char = e;code = 101 char = s;code = 115 char = s;code = 115 char = ;code = 32 char = i;code = 105 char = n;code = 110 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 = r;code = 114 char = e;code = 101 char = m;code = 109 char = o;code = 111 char = v;code = 118 char = a;code = 97 char = l;code = 108 char = .;code = 46 char = ;code = 32 char = M;code = 77 char = o;code = 111 char = d;code = 100 char = e;code = 101 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 = 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 = g;code = 103 char = l;code = 108 char = u;code = 117 char = t;code = 116 char = a;code = 97 char = t;code = 116 char = h;code = 104 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = e;code = 101 char = -;code = 45 char = B;code = 66 char = M;code = 77 char = C;code = 67 char = C;code = 67 char = ;code = 32 char = c;code = 99 char = o;code = 111 char = n;code = 110 char = j;code = 106 char = u;code = 117 char = g;code = 103 char = a;code = 97 char = t;code = 116 char = e;code = 101 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 = r;code = 114 char = a;code = 97 char = p;code = 112 char = i;code = 105 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 = l;code = 108 char = y;code = 121 char = s;code = 115 char = i;code = 105 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 = 97 char = d;code = 100 char = d;code = 100 char = u;code = 117 char = c;code = 99 char = t;code = 116 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = i;code = 105 char = m;code = 109 char = i;code = 105 char = d;code = 100 char = e;code = 101 char = ;code = 32 char = r;code = 114 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ,;code = 44 char = ;code = 32 char = b;code = 98 char = u;code = 117 char = t;code = 116 char = ;code = 32 char = n;code = 110 char = e;code = 101 char = i;code = 105 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = r;code = 114 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = c;code = 99 char = o;code = 111 char = n;code = 110 char = j;code = 106 char = u;code = 117 char = g;code = 103 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = ;code = 32 char = n;code = 110 char = o;code = 111 char = r;code = 114 char = ;code = 32 char = i;code = 105 char = t;code = 116 char = s;code = 115 char = ;code = 32 char = h;code = 104 char = y;code = 121 char = d;code = 100 char = r;code = 114 char = o;code = 111 char = l;code = 108 char = y;code = 121 char = s;code = 115 char = i;code = 105 char = s;code = 115 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 = t;code = 116 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 = e;code = 101 char = d;code = 100 char = ;code = 32 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = l;code = 108 char = e;code = 101 char = a;code = 97 char = s;code = 115 char = e;code = 101 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = e;code = 101 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 = p;code = 112 char = h;code = 104 char = i;code = 105 char = l;code = 108 char = e;code = 101 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = n;code = 110 char = e;code = 101 char = u;code = 117 char = t;code = 116 char = r;code = 114 char = a;code = 97 char = l;code = 108 char = ;code = 32 char = a;code = 97 char = q;code = 113 char = u;code = 117 char = e;code = 101 char = o;code = 111 char = u;code = 117 char = s;code = 115 char = ;code = 32 char = b;code = 98 char = u;code = 117 char = f;code = 102 char = f;code = 102 char = e;code = 101 char = r;code = 114 char = ;code = 32 char = a;code = 97 char = t;code = 116 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 = ;code = 32 char = r;code = 114 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = s;code = 115 char = .;code = 46 char = ;code = 32 char = T;code = 84 char = h;code = 104 char = e;code = 101 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 = l;code = 108 char = o;code = 111 char = w;code = 119 char = ;code = 32 char = B;code = 66 char = M;code = 77 char = C;code = 67 char = C;code = 67 char = ;code = 32 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 = 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 char = s;code = 115 char = ;code = 32 char = f;code = 102 char = a;code = 97 char = c;code = 99 char = i;code = 105 char = l;code = 108 char = e;code = 101 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = p;code = 112 char = a;code = 97 char = i;code = 105 char = r;code = 114 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = a;code = 97 char = t;code = 116 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 = i;code = 105 char = n;code = 110 char = ;code = 32 char = t;code = 116 char = r;code = 114 char = a;code = 97 char = n;code = 110 char = s;code = 115 char = i;code = 105 char = e;code = 101 char = n;code = 110 char = t;code = 116 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 = i;code = 105 char = o;code = 111 char = n;code = 110 char = ,;code = 44 char = ;code = 32 char = w;code = 119 char = h;code = 104 char = i;code = 105 char = c;code = 99 char = h;code = 104 char = ;code = 32 char = f;code = 102 char = a;code = 97 char = i;code = 105 char = l;code = 108 char = s;code = 115 char = ;code = 32 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = t;code = 116 char = r;code = 114 char = i;code = 105 char = g;code = 103 char = g;code = 103 char = e;code = 101 char = r;code = 114 char = ;code = 32 char = d;code = 100 char = a;code = 97 char = m;code = 109 char = a;code = 97 char = g;code = 103 char = e;code = 101 char = -;code = 45 char = s;code = 115 char = i;code = 105 char = g;code = 103 char = n;code = 110 char = a;code = 97 char = l;code = 108 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = p;code = 112 char = a;code = 97 char = t;code = 116 char = h;code = 104 char = w;code = 119 char = a;code = 97 char = y;code = 121 char = s;code = 115 char = .;code = 46 char = <;code = 60 char = b;code = 98 char = r;code = 114 char = /;code = 47 char = >;code = 62 result sql = The biotin-tagged electrophiles 1-biotinamido-4-(4'-[maleimidoethylcyclohexane]-carboxamido)butane (BMCC) and N-iodoacetyl-N-biotinylhexylenediamine (IAB) have been used as model electrophile probes in complex proteomes to identify protein targets associated with chemical toxicity. Whereas IAB activates stress signaling and apoptosis in HEK293 cells, BMCC does not. Cysteine Michael adducts formed from BMCC and nonbiotinylated analogues rapidly disappeared in the intact cells, whereas the adducts were stable in BMCC-treated subcellular fractions, even in the presence of the cellular reductants reduced glutathione, NADH, and NADPH. In contrast, cysteine thioether adducts formed from IAB and its nonbiotinylated analogues were stable in intact cells. Loss of the BMCC adduct in cells was reduced at 4 degrees C, which suggests the involvement of a metabolic process in adduct removal. Model studies with a glutathione-BMCC conjugate indicated rapid hydrolysis of the adducted imide ring, but neither the conjugate nor its hydrolysis product dissociated to release the electrophile in neutral aqueous buffer at significant rates. The results suggest that low BMCC toxicity reflects facile repair that results in transient adduction, which fails to trigger damage-signaling pathways.
Publication: Chem. Res. Toxicol. 2008 Dec ;21(12)::2361-9.
Publication Date: 2008 Dec
Study Author(s): Lin, De;Saleh, Samir;Liebler, Daniel C;
Institution: Department of Biochemistry, Vanderbilt Institute for Chemical Biology, Vanderbilt University School of Medicine, U1213C Medical Research Building III, 465 21st Avenue South, Nashville, Tennessee 37232, USA.
Shortcut link to this study:
The biotin-tagged electrophiles 1-biotinamido-4-(4'-[maleimidoethylcyclohexane]-carboxamido)butane (BMCC) and N-iodoacetyl-N-biotinylhexylenediamine (IAB) have been used as model electrophile probes in complex proteomes to identify protein targets associated with chemical toxicity. Whereas IAB activates stress signaling and apoptosis in HEK293 cells, BMCC does not. Cysteine Michael adducts formed from BMCC and nonbiotinylated analogues rapidly disappeared in the intact cells, whereas the adducts were stable in BMCC-treated subcellular fractions, even in the presence of the cellular reductants reduced glutathione, NADH, and NADPH. In contrast, cysteine thioether adducts formed from IAB and its nonbiotinylated analogues were stable in intact cells. Loss of the BMCC adduct in cells was reduced at 4 degrees C, which suggests the involvement of a metabolic process in adduct removal. Model studies with a glutathione-BMCC conjugate indicated rapid hydrolysis of the adducted imide ring, but neither the conjugate nor its hydrolysis product dissociated to release the electrophile in neutral aqueous buffer at significant rates. The results suggest that low BMCC toxicity reflects facile repair that results in transient adduction, which fails to trigger damage-signaling pathways.
PMID: 19548357