Chemical characterization of the invitro degradation products of vindesine sulfate

Thimmaiah, K. N. and Lloyd, W. D. and Sethi, V. S. (1990) Chemical characterization of the invitro degradation products of vindesine sulfate. Microchemical Journal, 42 (1). pp. 115-120.

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Abstract

Vindesine (VDS) was incubated in 0.2 M glycine buffer (pH 4.0, 7.4, or 8.8) containing bovine serum albumin (1%) at 37 °C for 24 or 72 h. The reaction mixture was extracted with CH2Cl2. HPLC analysis (μBondapak C18, 10 μm, reverse-phase steel column; isocratic solvent system: 50% MeOH in 10 mM KH2PO4, pH 4.0; flow rate, 1 ml/min; detector, 254 nm) of the extract gave three major peaks A, B, and C with retention times of 4.3, 5.3, and 13.0 min, respectively. At pH 8.8, peaks A and C accounted for about 11 and 28%, respectively, of the parent VDS. VDS in this system corresponded with peak B and its spectral data (UV, IR, MS, and 1H and 13C NMR) were identical to those of the parent compound. The UV, IR, and MS spectral properties of these peaks were as follows: peak A: UV (λmax): 208, 258, 290, 310 nm; IR (cm−1): 3450, 1731, 1673, 1611, 1503, 1460, 1380, 1228, 743; MS (): 752 (MH+); peak B: UV (λmax): 210, 263, 279, 290, 306 nm; IR (cm−1): 3457, 2922, 2850, 1723, 1676, 1500, 1456, 1369, 812, 733; MS (): 754 (MH+); peak C: UV (λmax): 212, 268, 280, 290, 310 nm; IR (cm−1): 3457, 2922, 2850, 1727, 1662, 1456, 1380, 1040, 740; MS (): 768 (MH+). On the basis of these spectral data and 1H NMR spectroscopy, peaks A and C are tentatively identified as an enamine/ether derivative of VDS and 3′,4′-epoxyvindesine N-oxide, respectively.

Item Type: Article
Uncontrolled Keywords: spectroscopy
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Dr Raju C
Date Deposited: 21 Jan 2021 09:47
Last Modified: 08 Jul 2022 05:17
URI: http://eprints.uni-mysore.ac.in/id/eprint/14351

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