Structural studies on the degradation products of vincristine dihydrogen sulfate

Sethi, V. S. and Thimmaiah, K. N. (1985) Structural studies on the degradation products of vincristine dihydrogen sulfate. Cancer Research, 45. pp. 5386-5389. ISSN 0008-5472

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Abstract

Vincristine was incubated at 37°C for 72 h in 0.2 M glycine buffer (pH 7.4 or 8.8) containing 1% bovine serum albumin. The reaction mixture was extracted with CH2CI2. High-performance liquid chromatography analysis (μBondapak C18 reverse-phase 10-μm steel column; solvent, 50% MeOH in 10 mM KH2P04, pH 4.5; flow rate, 1.2 ml/min) of the CH2CI2 extract gave 6 peaks, A, B, C, D, E, and F, with retention times of 4.8,6.5,10.0,12.5, 17.5, and 23.5 min, respectively. Peak C corresponded with vincristine. Spectroscopic data for these peak fractions were as follows UV (λmax); infrared (cm-1); mass spectrum (m/z): peak A: 220,256, and 295 nm; 3457,2922,1730, and 1669; and 783 (MH+); peak B: 218, 255, and 296 nm; 3435, 2922, 1731, and 1673; and 783 (MH+); peak C: 220, 255, and 296 nm; 3457, 2922, 1738, and 1680; and 825 (MH+); peak D: 218, 252, and 296 nm; 3385, 2922,1734, and 1677; and 825 (MH+); peak E: 208, 218, 252, and 298 nm; 3371, 2922, 1727, and 1665; and 768 (MH2+); and peak F: 209, 222, 255, and 296 nm; 3392, 2922,1734, and 1673; and 823 (MH+). These data suggest the following tentative structures for the degradation products: peak A, 4-deacetylvincristine; peak B, an isomer of 4-deacetylvincristine; peak D, an isomer of vincristine; peak E, 4-deacetyl-3-deoxyvincristine; and peak F, N-formylleurosine. The structure of peak A as 4-deacetylvincristine was confirmed by chemical synthesis. © 1985, American Association for Cancer Research. All rights reserved.

Item Type:	Article
Uncontrolled Keywords:	Mass, mass spectrometry, nonhuman, Spectrophotometry, priority journal, ultraviolet spectrophotometry, Non-U.S. Gov't, Support, drug identification, chromatography, Hydrogen-Ion Concentration, drug synthesis, vincristine, Vincristine, in vitro study, drug analysis, theoretical study, bovine serum albumin, buffer, chemical degradation, drug interaction, drug stability, glycine, high performance liquid chromatography, Infrared, Spectrum Analysis, Ultraviolet, 4 deacetyl 3 deoxyvincristine, deacetylvincristine, vinformide
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Dhruva Kumar
Date Deposited:	18 May 2021 10:07
Last Modified:	18 May 2021 10:07
URI:	http://eprints.uni-mysore.ac.in/id/eprint/13642

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