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Chemical Compound Review:

Michellamine A (1S,3S)-5-[3-[4-[(1S,3S)-6,8- dihydroxy-1,3...

Synonyms: Michellamine B, CHEMBL325222, CHEBI:66385, CHEBI:66386, NSC649324, ...

McMahon, J.B. et al., Supko, J.G. et al., Hallock, Y.F. et al., Hallock, Y.F. et al., Boyd, M.R. et al., et al.

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Disease relevance of AIDS-003609

HIV replication in cells in which infection was already fully established or in chronically infected cells was unaffected by michellamine B [1].

High impact information on AIDS-003609

Thus, michellamine B acts both at an early stage of the HIV life cycle by inhibiting RT as well as at later stages by inhibiting cellular fusion and syncytium formation [1].
Michellamine B (MB) is a naturally occurring naphthylisoquinoline alkaloid of novel chemical structure with activity against human immunodeficiency virus (HIV) types 1 and 2 in vitro [2].
Pharmacokinetics of michellamine B, a naphthylisoquinoline alkaloid with in vitro activity against human immunodeficiency virus types 1 and 2, in the mouse and dog [2].
Michellamine B exerted a potent dose-dependent inhibition of cell fusion in two independent cell-based fusion assays [1].
Biochemical studies showed that michellamine B inhibited the enzymatic activities of reverse transcriptases (RTs) from both HIV type 1 and HIV type 2 as well as two different nonnucleoside drug-resistant RTs with specific amino acid substitutions [1].

Anatomical context of AIDS-003609

Michellamine B inhibited HIV-induced cell killing and viral replication in a variety of human cell lines, as well as in cultures of human peripheral blood leukocytes and monocytes [3].

Associations of AIDS-003609 with other chemical compounds

Michellamines D-F exhibited in vitro HIV-inhibitory activity comparable to michellamine B, and korupensamine E exhibited in vitro antimalarial activity comparable to korupensamines A-D [4].

Analytical, diagnostic and therapeutic context of AIDS-003609

Preliminary results show that MEKC with LIF is feasible for the sensitive detection of michellamine B in serum [5].
A refined, three-step process (solvent-solvent partitioning, centrifugal partition chromatography and HPLC) has been developed and applied to the scaled-up production of michellamine B for preclinical drug development [6].
Determination of michellamine B in biological fluids by high-performance liquid chromatography with fluorescence detection [7].

References

Michellamine B, a novel plant alkaloid, inhibits human immunodeficiency virus-induced cell killing by at least two distinct mechanisms. McMahon, J.B., Currens, M.J., Gulakowski, R.J., Buckheit, R.W., Lackman-Smith, C., Hallock, Y.F., Boyd, M.R. Antimicrob. Agents Chemother. (1995) [Pubmed]
Pharmacokinetics of michellamine B, a naphthylisoquinoline alkaloid with in vitro activity against human immunodeficiency virus types 1 and 2, in the mouse and dog. Supko, J.G., Malspeis, L. Antimicrob. Agents Chemother. (1995) [Pubmed]
Anti-HIV michellamines from Ancistrocladus korupensis. Boyd, M.R., Hallock, Y.F., Cardellina, J.H., Manfredi, K.P., Blunt, J.W., McMahon, J.B., Buckheit, R.W., Bringmann, G., Schäffer, M., Cragg, G.M. J. Med. Chem. (1994) [Pubmed]
Michellamines D-F, new HIV-inhibitory dimeric naphthylisoquinoline alkaloids, and korupensamine E, a new antimalarial monomer, from Ancistrocladus korupensis. Hallock, Y.F., Manfredi, K.P., Dai, J.R., Cardellina, J.H., Gulakowski, R.J., McMahon, J.B., Schäffer, M., Stahl, M., Gulden, K.P., Bringmann, G., François, G., Boyd, M.R. J. Nat. Prod. (1997) [Pubmed]
Micellar electrokinetic chromatography of the anti-human immunodeficiency virus (HIV) agent michellamine B with absorption and laser-induced fluorescence detection. Chan, K.C., Majadly, F., McCloud, T.G., Muschik, G.M., Issaq, H.J., Snader, K.M. Electrophoresis (1994) [Pubmed]
Preparative separation of naphthyltetrahydroisoquinoline alkaloids from Ancistrocladus korupensis by centrifugal partition chromatography. Hallock, Y.F., Dai, J., Bokesch, H.R., Dillah, K.B., Manfredi, K.P., Cardellina, J.H., Boyd, M.R. Journal of chromatography. A. (1994) [Pubmed]
Determination of michellamine B in biological fluids by high-performance liquid chromatography with fluorescence detection. Supko, J.G., Malspeis, L. Anal. Biochem. (1994) [Pubmed]

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