Molecular lipophilicity determination of a huperzine series by HPLC: comparison of C18 and IAM stationary phases.
Two hydrophobic parameters (logkw-C18 and logkw-IAM, respectively) of a huperzine A series were extrapolated by high performance liquid chromatography (HPLC) using both C18 and immobilised artificial membrane (IAM) columns. A mathematical correlation between C18 and IAM hydrophobic parameters was completed, suggesting a similar behaviour on both columns. This behaviour was principally led by hydrophobic forces. The theoretical lipophilicity (logP) of each compound was computed using Pallas software and compared to experimental values, showing a similar lipophilic behaviour. Finally, the huperzine logkw-IAM and logkw-C18 values were correlated with the relative bound percentage of huperzine in human serum albumin, confirming that hydrophobic forces are predominant in the huperzine-HSA binding mechanism.
Darrouzain
François
F
Equipe des Sciences Séparatives et Biopharmaceutiques (2SB, EA/3924), Laboratoire de Chimie Analytique et de Chimie Thérapeutique, Faculté de Médecine et de Pharmacie, Place Saint-Jacques, 25030 Besançon cedex, France.
Dallet
Philippe
P
Dubost
Jean-Pierre
JP
Ismaili
Lhassane
L
Pehourcq
Fabienne
F
Bannwarth
Bernard
B
Matoga
Myriam
M
Guillaume
Yves C
YC
D000470:Alkaloids; D055598:Chemical Phenomena; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002627:Chemistry, Physical; D002845:Chromatography / Q000379:methods*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D007700:Kinetics; D008567:Membranes, Artificial; D008956:Models, Chemical; D008962:Models, Theoretical; D004364:Pharmaceutical Preparations; D012717:Sesquiterpenes / Q000032:analysis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D012984:Software; D013678:Technology, Pharmaceutical / Q000379:methods*
D000470:Alkaloids; D008567:Membranes, Artificial; D004364:Pharmaceutical Preparations; D012717:Sesquiterpenes; D012821:Silanes; C050426:huperzine A; C061189:octadecyltrichlorosilane