Sethi, V. S. and Thimmaiah, K. N. (1985) Chemical characterization of the degradation products of vinblastine dihydrogen sulfate. Cancer Research, 45. pp. 5382-5385. ISSN 0008-5472
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Vinblastine was incubated in 0.2 M glycine buffer (pH 7.4 or 8.8) containing bovine serum albumin (1%) at 37°C for 72 h. The reaction mixture was extracted with CH2CI2, and the extract gave 6 major peaks (A, B, C, D, E, and F) with retention times of 5.0, 7.5, 11.0, 13.0, 23.0, and 30.0 min, respectively, in a high-performance liquid chromatography system (⌃Bondapak C18 column; solvent, 50% MeOH in 10 mM KH2P04, pH 4.5; flow rate, 1.2 ml/min; detector, 254 nm). Vinblastine in this system corresponded with peak C, and its spectral data were identical to those of the parent compound. The UV, infrared, and mass spectral properties of these peaks were as follows UV (λmax); infrared (cmâ��1); mass spectrum (m/z): peak A: 214, 266, and 315 nm; 3464, 2850, and 1730; and 769 (MH+); peak B: 213, 258, 285, and 295 nm; 3457, 2951, 2580, and 1734; and 809 (MH+); peak C: 214, 266, 292, and 312 nm; 3457, 2951, and 1734; and 811 (MH+); peak D: 212,266,285, and 312 nm; 3467, 2915, and 1734; and 811 (MH+); peak E: 212, 260, 285, 294, and 313 nm; 3479, 2850, and 1734; and 825 (MH+); and peak F: 212, 265, 283, and 312 nm; 3407, 2857, and 1734; and 807 (MH+). These data suggest the following tentative structures for the degradation products: peak A, 4-deacetylvinblastine; peak B, 19'-hydroxy-3',4'-dehydrovinblastine; peak D, an isomer of vinblastine; peak E, 19'-oxovinblastine; and peak F, 3',4'-de-hydro-19'-oxovinblastine. The structure of peak A as 4-deacetylvinblastine was further 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, drug synthesis, 3', in vitro study, drug analysis, theoretical study, 19' oxovinblastine, 4' dehydro 19' hydroxyvinblastine, 4' dehydro 19' oxovinblastine, bovine serum albumin, buffer, chemical degradation, deacetylvinblastine, drug interaction, drug stability, glycine, high performance liquid chromatography, Infrared, infrared spectrometry, Spectrum Analysis, Ultraviolet, vinblastine, Vinblastine, vinblastine sulfate |
| Subjects: | C Chemical Science > Chemistry |
| Divisions: | Department of > Chemistry |
| Depositing User: | Dhruva Kumar |
| Date Deposited: | 18 May 2021 10:03 |
| Last Modified: | 18 May 2021 10:03 |
| URI: | http://eprints.uni-mysore.ac.in/id/eprint/13641 |
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