Chiral high-performance liquid chromatographic separations of vinca alkaloid analogues on alpha 1-acid glycoprotein and human serum albumin columns

• Published in: Journal of chromatography Vol. 609; no. 1-2; p. 163
• Main Authors: Fitos, I, Visy, J, Simonyi, M, Hermansson, J
• Format: Journal Article
• Language: English
• Published: Netherlands 18.09.1992
• Subjects: Chromatography, High Pressure Liquid - methods; Humans; Hydrogen-Ion Concentration; Molecular Structure; Orosomucoid; Serum Albumin; Stereoisomerism; Vinca Alkaloids - chemistry; Vinca Alkaloids - isolation & purification
• DOI: 10.1016/0021-9673(92)80159-R

Separations of the stereoisomers of a series of tetracyclic and pentacyclic vinca alkaloid analogues having two or three chiral centres were performed on Chiral-AGP and Chiral-HSA high-performance liquid chromatographic columns. Phosphate buffers with pH 5-7 containing 5-35% acetonitrile or 2-propanol were used as mobile phases. The results were in accordance with previous binding data obtained with native AGP and on an HSA-Sepharose column. Whereas on Chiral-AGP the retention of the trans isomers having 1(R),12b(S)-indolo[2,3-a]quinolizidine or the corresponding 3(S),16(R)-eburnane absolute configurations was exceedingly high, on Chiral-HSA the trans isomers, independently of their absolute configurations, were more retained. Eburnane-type compounds could also be separated according to the configuration of the chiral centre at position 14. A comparison of the chromatographic properties of the vinca alkaloids on the Chiral-AGP and Chiral-HSA columns demonstrates that these compounds are bound with higher affinity to the AGP phase. The AGP column resolves a very broad range of vinca alkaloids compared with the HSA column. Higher stereoselectivity and a much better chromatographic performance were also obtained on the Chiral-AGP column.