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Antimicrobial Agents and Chemotherapy, May 2004, p. 1614-1623, Vol. 48, No. 5
0066-4804/04/$08.00+0     DOI: 10.1128/AAC.48.5.1614-1623.2004
Copyright © 2004, American Society for Microbiology. All Rights Reserved.

Novel Polysulfated Galactose-Derivatized Dendrimers as Binding Antagonists of Human Immunodeficiency Virus Type 1 Infection

Richard D. Kensinger,1,{dagger} Bradley J. Catalone,2,{ddagger} Fred C. Krebs,2,§ Brian Wigdahl,2,§ and Cara-Lynne Schengrund1*

Department of Biochemistry and Molecular Biology,1 Department of Microbiology and Immunology, The Pennsylvania State University College of Medicine, Hershey, Pennsylvania 170332

Received 4 September 2003/ Returned for modification 13 November 2003/ Accepted 3 February 2004

Evidence indicates that galactosyl ceramide (GalCer) and its 3'-sulfated derivative, sulfatide (SGalCer), may act as alternate coreceptors for human immunodeficiency virus type 1 (HIV-1) in CD4– cells. Glycosphingolipids (GSLs) may also be necessary for fusion of HIV-1 and host cell membranes. Using an enzyme-linked immunosorbent assay to determine which GSL was the best ligand for both recombinant and virus-associated gp120, we found that SGalCer was the best ligand for each rgp120 and HIV-1 isolate tested. Therefore, novel multivalent glycodendrimers, which mimic the carbohydrate clustering reportedly found in lipid rafts, were synthesized based on the carbohydrate moiety of SGalCer. Here we describe the synthesis of a polysulfated galactose functionalized, fifth generation DAB dendrimer (PS Gal 64mer), containing on average two sulfate groups per galactose residue. Its ability to inhibit HIV-1 infection of cultured indicator cells was compared to that of dextran sulfate (DxS), a known, potent, binding inhibitor of HIV-1. The results indicate that the PS Gal 64mer inhibited infection by the HIV-1 isolates tested as well as DxS.

* Corresponding author. Mailing address: Department of Biochemistry and Molecular Biology, The Pennsylvania State University College of Medicine, 500 University Dr., Hershey, PA 17033. Phone: (717) 531-8048. Fax: (717) 531-7072. E-mail: cxs8{at}psu.edu.

{dagger} Present address: Aventis Pasteur, Swiftwater, PA 18370.

{ddagger} Present address: Chesapeake Biological Labs, Inc., Baltimore, MD 21230-2591.

§ Present address: Department of Microbiology and Immunology, Drexel University College of Medicine, Philadelphia, PA 19129.

Antimicrobial Agents and Chemotherapy, May 2004, p. 1614-1623, Vol. 48, No. 5
0066-4804/04/$08.00+0     DOI: 10.1128/AAC.48.5.1614-1623.2004
Copyright © 2004, American Society for Microbiology. All Rights Reserved.



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