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Chemical Compound Review:

AG-K-42292 (3S,5S,10S,13S)-17-[(1R)-1- hydroxy-1-(2...

Synonyms: AC1LAT5F, CTK7F3070, 22,26-Azasterol

Urbina, J.A. et al., Urbina, J.A. et al., Rodrigues, J.C. et al., Palmié-Peixoto, I.V. et al.

Urbina, Visbal, Contreras, McLaughlin, Docampo,

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High impact information on AIDS-082332

Transmission electron microscopy showed that 22,26-azasterol induced marked morphological changes, including mitochondrial swelling, invaginations of the inner mitochondrial membrane, and the appearance of large bodies containing concentric membranes [1].
To investigate the physiological significance of these sterols, cultures of P. carinii in embryonic lung cells were exposed to 22,26-azasterol (20-piperidin-2-yl-5alpha-pregnan-3beta-20(R)-diol), a compound previously shown to inhibit both enzymes and to halt cell proliferation in fungi and protozoa [2].
Both sterol analogs produced a dose-dependent reduction in the incorporation of radioactivity from [methyl-14C]methionine with IC50 values of 640 nM and 70 nM for 22,26-azasterol and 24,25-(R,S)-epiminolanosterol, respectively, indicating a specific inhibition of 24(25)-SMT [3].
Concurrently, a dramatic reduction of 24-alkyl sterols was observed after 22,26-azasterol treatment, both in whole cell homogenates, as well as in isolated mitochondria [4].

References

Ultrastructural and biochemical alterations induced by 22,26-azasterol, a delta(24(25))-sterol methyltransferase inhibitor, on promastigote and amastigote forms of Leishmania amazonensis. Rodrigues, J.C., Attias, M., Rodriguez, C., Urbina, J.A., Souza, W. Antimicrob. Agents Chemother. (2002) [Pubmed]
Inhibitors of delta24(25) sterol methyltransferase block sterol synthesis and cell proliferation in Pneumocystis carinii. Urbina, J.A., Visbal, G., Contreras, L.M., McLaughlin, G., Docampo, R. Antimicrob. Agents Chemother. (1997) [Pubmed]
Modification of the sterol composition of Trypanosoma (Schizotrypanum) cruzi epimastigotes by delta 24(25)-sterol methyl transferase inhibitors and their combinations with ketoconazole. Urbina, J.A., Vivas, J., Visbal, G., Contreras, L.M. Mol. Biochem. Parasitol. (1995) [Pubmed]
Effects of sterol biosynthesis inhibitors on endosymbiont-bearing trypanosomatids. Palmié-Peixoto, I.V., Rocha, M.R., Urbina, J.A., de Souza, W., Einicker-Lamas, M., Motta, M.C. FEMS Microbiol. Lett. (2006) [Pubmed]

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