Doxorubicin inhibits oxidation of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) by a lactoperoxidase/H(2)O(2) system by reacting with ABTS-derived radical.
The effect of doxorubicin on oxidation of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) by lactoperoxidase and hydrogen peroxide has been investigated. It was found that: (1) oxidation of ABTS to its radical cation (ABTS*(+)) is inhibited by doxorubicin as evidenced by its induction of a lag period, duration of which depends on doxorubicin concentration; (2) the inhibition is due to doxorubicin hydroquinone reducing the ABTS*(+) radical (stoichiometry 1: 1.8); (3) concomitant with the ABTS*(+) reduction is oxidation of doxorubicin; only when the doxorubicin concentration decreases to a near zero level, net oxidation of ABTS could be detected; (4) oxidation of doxorubicin leads to its degradation to 3-methoxysalicylic acid and 3-methoxyphthalic acid; (5) the efficacy of doxorubicin to quench ABTS*(+) is similar to the efficacy of p-hydroquinone, glutathione and Trolox C. These observations support the assertion that under certain conditions doxorubicin can function as an antioxidant. They also suggest that interaction of doxorubicin with oxidants may lead to its oxidative degradation.
Reszka
Krzysztof J
KJ
Research Service, VA Medical Center, Cincinnati, OH 45230, USA. reszkakj@ucmail.uc.edu
Britigan
Bradley E
BE
D000903:Antibiotics, Antineoplastic / Q000737:chemistry*; D052160:Benzothiazoles; D002839:Chromans / Q000737:chemistry; D004317:Doxorubicin / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D005978:Glutathione / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry*; D006873:Hydroquinones / Q000737:chemistry; D007784:Lactoperoxidase / Q000737:chemistry*; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D010795:Phthalic Acids / Q000737:chemistry; D012459:Salicylates / Q000737:chemistry; D013451:Sulfonic Acids / Q000737:chemistry*; D013844:Thiazoles / Q000737:chemistry*
C483040:3-methoxyphthalic acid; D000903:Antibiotics, Antineoplastic; D052160:Benzothiazoles; D002839:Chromans; D005609:Free Radicals; D006873:Hydroquinones; D016877:Oxidants; D010795:Phthalic Acids; D012459:Salicylates; D013451:Sulfonic Acids; D013844:Thiazoles; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C523953:3-methoxysalicylic acid; D004317:Doxorubicin; D006861:Hydrogen Peroxide; D007784:Lactoperoxidase; D005978:Glutathione; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid; C031927:hydroquinone