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result sql = An investigation into copper catalyzed D-penicillamine oxidation and subsequent hydrogen peroxide generation.
An investigation into copper catalyzed D-penicillamine oxidation and subsequent hydrogen peroxide generation.
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char = T;code = 84
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char = a;code = 97
char = l;code = 108
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char = z;code = 122
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char = D;code = 68
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char = l;code = 108
char = a;code = 97
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char = l;code = 108
char = t;code = 116
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 = n;code = 110
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char = o;code = 111
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char = r;code = 114
char = a;code = 97
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char = i;code = 105
char = o;code = 111
char = n;code = 110
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char = o;code = 111
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char = i;code = 105
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char = a;code = 97
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char = o;code = 111
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char = f;code = 102
char = e;code = 101
char = r;code = 114
char = r;code = 114
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char = c;code = 99
char = h;code = 104
char = l;code = 108
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char = d;code = 100
char = e;code = 101
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char = t;code = 116
char = e;code = 101
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char = e;code = 101
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char = u;code = 117
char = r;code = 114
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char = p;code = 112
char = H;code = 72
char = ,;code = 44
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char = a;code = 97
char = n;code = 110
char = a;code = 97
char = e;code = 101
char = r;code = 114
char = o;code = 111
char = b;code = 98
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char = c;code = 99
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char = c;code = 99
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char = e;code = 101
char = l;code = 108
char = a;code = 97
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char = o;code = 111
char = r;code = 114
char = s;code = 115
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char = s;code = 115
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char = a;code = 97
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char = ;code = 32
char = e;code = 101
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char = h;code = 104
char = y;code = 121
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char = i;code = 105
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char = e;code = 101
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char = a;code = 97
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char = e;code = 101
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char = i;code = 105
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char = i;code = 105
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char = m;code = 109
char = p;code = 112
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char = a;code = 97
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char = H;code = 72
char = P;code = 80
char = L;code = 76
char = C;code = 67
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char = a;code = 97
char = s;code = 115
char = s;code = 115
char = a;code = 97
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char = s;code = 115
char = u;code = 117
char = l;code = 108
char = t;code = 116
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char = h;code = 104
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char = o;code = 111
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char = u;code = 117
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char = o;code = 111
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char = i;code = 105
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char = e;code = 101
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char = g;code = 103
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char = ;code = 32
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char = e;code = 101
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result sql = D-Penicillamine is a potent copper (Cu) chelating agent. D-Pen reduces Cu(II) to Cu(I) in the process of chelation while at the same time being oxidized to D-penicillamine disulfide. It has been proposed that hydrogen peroxide is generated during this process. However, definitive experimental proof that hydrogen peroxide is generated remains lacking. Thus, the major aims of these studies were to confirm and quantitatively assess the in vitro production of hydrogen peroxide during copper catalyzed D-penicillamine oxidation. The potential cytotoxic effect of hydrogen peroxide generation was also investigated in vitro against MCF-7 human breast cancer cells. Cell cytotoxicity resulting from the incubation of D-penicillamine with copper was compared to that of D-penicillamine, copper and hydrogen peroxide. The mechanism of copper catalyzed D-penicillamine oxidation and simultaneous hydrogen peroxide production was investigated as a function of time, concentration of cupric sulfate or ferric chloride, temperature, pH, anaerobic condition and chelators such as ethylenediaminetetraacetic acid and bathocuproinedisulfonic acid. A simple, sensitive and rapid HPLC assay was developed to simultaneously detect D-penicillamine, its major oxidation product D-penicillamine disulfide, and hydrogen peroxide in a single run. Hydrogen peroxide was shown to be generated in a concentration dependent manner as a result of D-penicillamine oxidation in the presence of cupric sulfate. Chelators such as ethylenediaminetetraacetic acid and bathocuproinedisulfonic acid were able to inhibit D-penicillamine oxidation. The incubation of MCF-7 human breast cancer cells with D-penicillamine plus cupric sulfate resulted in the production of reactive oxygen species within the cell and cytotoxicity that was comparable to free hydrogen peroxide.

Publication: J. Inorg. Biochem. 2007 Apr ;101(4)::594-602.
Publication Date: 2007 Apr
Study Author(s): Gupte, Anshul;Mumper, Russell J;
Institution: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, 725 Rose Street, Lexington, KY 40536-0082, USA.
Shortcut link to this study:
D-Penicillamine is a potent copper (Cu) chelating agent. D-Pen reduces Cu(II) to Cu(I) in the process of chelation while at the same time being oxidized to D-penicillamine disulfide. It has been proposed that hydrogen peroxide is generated during this process. However, definitive experimental proof that hydrogen peroxide is generated remains lacking. Thus, the major aims of these studies were to confirm and quantitatively assess the in vitro production of hydrogen peroxide during copper catalyzed D-penicillamine oxidation. The potential cytotoxic effect of hydrogen peroxide generation was also investigated in vitro against MCF-7 human breast cancer cells. Cell cytotoxicity resulting from the incubation of D-penicillamine with copper was compared to that of D-penicillamine, copper and hydrogen peroxide. The mechanism of copper catalyzed D-penicillamine oxidation and simultaneous hydrogen peroxide production was investigated as a function of time, concentration of cupric sulfate or ferric chloride, temperature, pH, anaerobic condition and chelators such as ethylenediaminetetraacetic acid and bathocuproinedisulfonic acid. A simple, sensitive and rapid HPLC assay was developed to simultaneously detect D-penicillamine, its major oxidation product D-penicillamine disulfide, and hydrogen peroxide in a single run. Hydrogen peroxide was shown to be generated in a concentration dependent manner as a result of D-penicillamine oxidation in the presence of cupric sulfate. Chelators such as ethylenediaminetetraacetic acid and bathocuproinedisulfonic acid were able to inhibit D-penicillamine oxidation. The incubation of MCF-7 human breast cancer cells with D-penicillamine plus cupric sulfate resulted in the production of reactive oxygen species within the cell and cytotoxicity that was comparable to free hydrogen peroxide.
PMID: 17275091

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