Physical factors contributing to the partition coefficient and retention time of 2',3'-dideoxynucleoside analogues.
Acquired immunodeficiency syndrome (AIDS) is an immunosuppressive disease characterized by an immune impairment and a high susceptibility to unusual forms of certain neoplasms. Since the brain is an important site of the infection, it is necessary to explore new classes of drugs that have the ability to penetrate across the blood-brain barrier, and the potency to suppress viral replication within the central nervous system (CNS). Therefore, the ability to predicate the lipophilicity of the potent anti-AIDS drugs may provide useful information about the potential of the drugs to enter CNS. In this paper, the correlations of log P (octanol-buffer partition coefficient) and log tR (retention time in HPLC; Rt was used by Balzarini et al.) with some physical constants like log MW (molecular weight), hydrogen bond forming ability (HB) of the substituents, and the substituent group dipole moments (mu) are analyzed. Good correlations of log P and log tR with log MW, HB, and mu have been obtained.
Division of Biomedicinal Chemistry, School of Pharmacy, University of Southern California, Los Angeles 90033.
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EJ
Lien
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Gao
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Prabhakar
D000998:Antiviral Agents / Q000737:chemistry; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D015224:Dideoxynucleosides / Q000737:chemistry*; D008970:Molecular Weight; D011741:Pyrimidine Nucleosides / Q000737:chemistry; D012044:Regression Analysis; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D015224:Dideoxynucleosides; D011741:Pyrimidine Nucleosides