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ID: ALA4813943

Journal: J Med Chem

Title: Hybrids of Small-Molecule CD4 Mimics with Polyethylene Glycol Units as HIV Entry Inhibitors.

Authors: Kobayakawa T, Tsuji K, Konno K, Himeno A, Masuda A, Yang T, Takahashi K, Ishida Y, Ohashi N, Kuwata T, Matsumoto K, Yoshimura K, Sakawaki H, Miura T, Harada S, Matsushita S, Tamamura H.

Abstract: CD4 mimics are small molecules that inhibit the interaction of gp120 with CD4. We have developed several CD4 mimics. Herein, hybrid molecules consisting of CD4 mimics with a long alkyl chain or a PEG unit attached through a self-cleavable linker were synthesized. In anti-HIV activity, modification with a PEG unit appeared to be more suitable than modification with a long alkyl chain. Thus, hybrid molecules of CD4 mimics, with PEG units attached through an uncleavable linker, were developed and showed high anti-HIV activity and low cytotoxicity. In investigation of pharmacokinetics in a rhesus macaque, a hybrid compound had a more effective PK profile than that of the parent compound, and intramuscular injection was a more useful administration route to maintain the high blood concentration of the CD4 mimic than intravenous injection. The presented hybrid molecules of CD4 mimics with a PEG unit would be practically useful when combined with a neutralizing antibody.

CiteXplore: 33497209

DOI: 10.1021/acs.jmedchem.0c01153