Horseradish peroxidase/hydrogen peroxide-catalyzed oxidation of VP16-213. Identification of a new metabolite.
作者： Massimo Broggini , Cosmo Rossi , Emilio Benfenati , Maurizio D'Incalci , Roberto Fanelli
DOI: 10.1016/S0009-2797(85)80129-0
关键词: Horseradish peroxidase 、 Medicinal chemistry 、 Metabolite 、 Peroxidase 、 Hydrogen peroxide 、 Chromatography 、 High-performance liquid chromatography 、 Ring (chemistry) 、 Catalysis 、 Chemistry 、 Mass spectrometry
摘要: Summary VP16 was submitted to oxidation catalyzed by horseradish peroxidase (HRP) and H 2 O in phosphate buffer (pH 7.0). The product of the reaction, which has a high performance liquid chromatographic (HPLC) retention time different from previously known metabolites VP16, identified as 1,2,3,4-tetradehydro-VP16 1 H-NMR mass spectrometry (MS) analysis. It found result loss four hydrogens formation an aromatic ring (ring B VP16). This new retains, 4′ position E hydroxy group is crucial for antitumoral activity podophyllotoxin derivatives. reaction linear wide range concentrations dependent on concomitant presence .
elsevier.com
sci-hub.se 参考文章(15)
J.M. Lasker, K. Sivarajah, R.P. Mason, B. Kalyanaraman, M.B. Abou-Donia, T.E. Eling, A free radical mechanism of prostaglandin synthase-dependent aminopyrine demethylation. Journal of Biological Chemistry. ,vol. 256, pp. 7764- 7767 ,(1981) , 10.1016/S0021-9258(18)43342-X
Bonnie S. Glisson, Warren E. Ross, Antoinette J. Wozniak, Kenneth R. Hande, Inhibition of Etoposide-induced DNA Damage and Cytotoxicity in L1210 Cells by Dehydrogenase Inhibitors and Other Agents Cancer Research. ,vol. 44, pp. 626- 632 ,(1984)
Warren E. Ross, Antoinette J. Wozniak, DNA Damage as a Basis for 4′-Demethylepipodophyllotoxin-9-(4,6-O-ethylidene-β-d-glucopyranoside) (Etoposide) Cytotoxicity Cancer Research. ,vol. 43, pp. 120- 124 ,(1983)
WilliamE. Evans, JosephA. Sinkule, WilliamR. Crom, Lois Dow, A.Thomas Look, Gaston Rivera, Pharmacokinetics of Teniposide (VM26) and etoposide (VP16-213) in children with cancer. Cancer Chemotherapy and Pharmacology. ,vol. 7, pp. 147- 150 ,(1982) , 10.1007/BF00254537
Marcel Rozencweig, Daniel D. Von Hoff, Jane E. Henney, Franco M. Muggia, VM 26 and VP 16–213: A comparative analysis Cancer. ,vol. 40, pp. 334- 342 ,(1977) , 10.1002/1097-0142(197707)40:1<334::AID-CNCR2820400147>3.0.CO;2-X
Kenneth V. Honn, Richard S. Bockman, Lawrence J. Marnett, Prostaglandins and cancer: A review of tumor initiation through tumor metastasis Prostaglandins. ,vol. 21, pp. 833- 864 ,(1981) , 10.1016/0090-6980(81)90240-9
John D. Loike, Susan B. Horwitz, Effect of VP-16-213 on the intracellular degradation of DNA in HeLa cells. Biochemistry. ,vol. 15, pp. 5443- 5448 ,(1976) , 10.1021/BI00670A004
Hartmut Jungclas, Harald Danigel, Lothar Schmidt, Liquid chromatography/mass spectrometry with 252Cf fission fragment induced ionization International Journal of Mass Spectrometry and Ion Physics. ,vol. 46, pp. 197- 200 ,(1983) , 10.1016/0020-7381(83)80087-4
Birandra K. Sinha, Michael A. Trush, Balaraman Kalyanaraman, Free radical metabolism of VP-16 and inhibition of anthracycline-induced lipid peroxidation Biochemical Pharmacology. ,vol. 32, pp. 3495- 3498 ,(1983) , 10.1016/0006-2952(83)90385-4
L W Dow, J A Sinkule, W E Evans, A Horvath, A T Look, Comparative cytotoxic and cytokinetic effects of the epipodophyllotoxins 4'-demethylepipodophyllotoxin-9-(4,6-O-2-ethylidene-beta-D-glucopyranoside) and 4'-demethylepipodophyllotoxin-9-(4,6-O-2-thenylidene-beta-D-glucopyranoside) and their metabolites on human leukemic lymphoblasts Cancer Research. ,vol. 43, pp. 5699- 5706 ,(1983)