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Chemical Compound Review:

BuCast [(1S,6S,7S,8R,8aR)-1,7,8- trihydroxy-1,2,3...

Synonyms: Celgosivir, B-CAST, VIR-222, SureCN135812, MBI-3253, ...

Bridges, C.G. et al., Taylor, D.L. et al., Taylor, D.L. et al., Whitby, K. et al., Ahmed, S.P. et al., et al.

Whitby, Taylor, Patel, Ahmed, Tyms,

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Disease relevance of B-CAST

HIV-1 glycoproteins, gp160 and gp120, synthesized in H9 cells chronically infected with HIV-1 (RF) and treated with MDL 28,574, were characterized by an increase in relative molecular weight of approximately 7-8000 kD [1].
The effect of oral treatment with 6-O-butanoyl castanospermine (MDL 28,574) in the murine zosteriform model of HSV-1 infection [2].
Antiviral activity and metabolism of the castanospermine derivative MDL 28,574, in cells infected with herpes simplex virus type 2 [3].
The alpha-glucosidase 1 inhibitor 6-O-butanoyl castanospermine (MDL 28574) has antiviral activity for HIV which is manifested by a decrease in syncytia as well as the production of virus with altered gp120 and a reduced infectivity (Taylor et al., 1991) [4].
The observation that the number of viral genomes released from BVDV-infected cells was inhibited by either castanospermine or celgosivir in parallel with the number of infectious units was taken as confirmation that these alpha-glucosidase I inhibitors block the production or release of flavivirus particles [5].

High impact information on B-CAST

We now report that consistent with its improved anti-HIV activity, MDL 28,574 is more effective (50% inhibitory concentration [IC50], 20 microM) than the parent molecule (IC50, 254 microM) at causing the accumulation of glucosylated oligosaccharides in HIV-infected cells by inhibition of glycoprotein processing [6].
Previously, it has been shown that the alpha-glucose 1 inhibitor (MDL 28574) treatment of human leukocytes in vitro or mouse lymphocytes in vivo affects the detection of LFA-1 but not domain 1 of CD4 nor several other CD markers (Bridges et al., submitted for publication) [4].
The most effective analogue was 6-O-butanoyl CAST (B-CAST, MDL 28,574) with an IC50 of 0.05 micrograms/mL against MOLV [7].

Analytical, diagnostic and therapeutic context of B-CAST

MDL 28,574 was at least 50 times more active than BuDNJ and less active but better tolerated in cell culture than ddC, two compounds currently undergoing clinical trials [1].

References

6-0-butanoylcastanospermine (MDL 28,574) inhibits glycoprotein processing and the growth of HIVs. Taylor, D.L., Sunkara, P.S., Liu, P.S., Kang, M.S., Bowlin, T.L., Tyms, A.S. AIDS (1991) [Pubmed]
The effect of oral treatment with 6-O-butanoyl castanospermine (MDL 28,574) in the murine zosteriform model of HSV-1 infection. Bridges, C.G., Ahmed, S.P., Kang, M.S., Nash, R.J., Porter, E.A., Tyms, A.S. Glycobiology (1995) [Pubmed]
Antiviral activity and metabolism of the castanospermine derivative MDL 28,574, in cells infected with herpes simplex virus type 2. Ahmed, S.P., Nash, R.J., Bridges, C.G., Taylor, D.L., Kang, M.S., Porter, E.A., Tyms, A.S. Biochem. Biophys. Res. Commun. (1995) [Pubmed]
The prevention of cell adhesion and the cell-to-cell spread of HIV-1 in vitro by the alpha-glucosidase 1 inhibitor, 6-O-butanoyl castanospermine (MDL 28574). Bridges, C.G., Brennan, T.M., Taylor, D.L., McPherson, M., Tyms, A.S. Antiviral Res. (1994) [Pubmed]
Action of celgosivir (6 O-butanoyl castanospermine) against the pestivirus BVDV: implications for the treatment of hepatitis C. Whitby, K., Taylor, D., Patel, D., Ahmed, P., Tyms, A.S. Antivir. Chem. Chemother. (2004) [Pubmed]
Inhibition of alpha-glucosidase I of the glycoprotein-processing enzymes by 6-O-butanoyl castanospermine (MDL 28,574) and its consequences in human immunodeficiency virus-infected T cells. Taylor, D.L., Kang, M.S., Brennan, T.M., Bridges, C.G., Sunkara, P.S., Tyms, A.S. Antimicrob. Agents Chemother. (1994) [Pubmed]
Inhibition of glycoprotein processing and HIV replication by castanospermine analogues. Sunkara, P.S., Kang, M.S., Bowlin, T.L., Liu, P.S., Tyms, A.S., Sjoerdsma, A. Ann. N. Y. Acad. Sci. (1990) [Pubmed]

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