Chiral high-performance liquid chromatographic separations of vinca alkaloid analogues on alpha 1-acid glycoprotein and human serum albumin columns.
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.
Fitos
I
I
Central Research Institute for Chemistry, Hungarian Academy of Sciences, Budapest.
Visy
J
J
Simonyi
M
M
Hermansson
J
J
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D006801:Humans; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D009961:Orosomucoid; D012709:Serum Albumin; D013237:Stereoisomerism; D014748:Vinca Alkaloids / Q000737:chemistry / Q000302:isolation & purification*
D009961:Orosomucoid; D012709:Serum Albumin; D014748:Vinca Alkaloids