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Steroids. 2014 Oct;88:95-100. doi: 10.1016/j.steroids.2014.06.020. Epub 2014 Jul 8.

Microbial transformation of nandrolone with Cunninghamella echinulata and Cunninghamella blakesleeana and evaluation of leishmaniacidal activity of transformed products.

Author information

1
Department of Biology, American University of Beirut, Beirut 1107 2020, Lebanon. Electronic address: eliasbay@aub.edu.lb.
2
Department of Biology, American University of Beirut, Beirut 1107 2020, Lebanon.
3
Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
4
H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.
5
Department of Biology, University of Balamand, Koura 100, Lebanon.
6
Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan; H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan; Department of Biochemistry, Faculty of Science, King Abdulaziz Universisty. Jeddah 21412, Saudi Arabia. Electronic address: iqbal.choudhary@iccs.edu.

Abstract

Therapeutic potential of nandrolone and its derivatives against leishmaniasis has been studied. A number of derivatives of nandrolone (1) were synthesized through biotransformation. Microbial transformation of nandrolone (1) with Cunninghamella echinulata and Cunninghamella blakesleeana yielded three new metabolites, 10β,12β,17β-trihydroxy-19-nor-4-androsten-3-one (2), 10β,16α,17β-trihydroxy-19-nor-4-androsten-3-one (3), and 6β,10β,17β-trihydroxy-19-nor-4-androsten-3-one (4), along with four known metabolites, 10β,17β-dihydroxy-19-nor-4-androsten-3-one (5), 6β,17β-dihydroxy-19-nor-4-androsten-3-one (6) 10β-hydroxy-19-nor-4-androsten-3,17-dione (7) and 16β,17β-dihydroxy-19-nor-4-androsten-3-one (8). Compounds 1-8 were evaluated for their anti-leishmanial activity. Compounds 1 and 8 showed a significant activity in vitro against Leishmania major. The leishmanicidal potential of compounds 1-8 (IC50=32.0±0.5, >100, 77.39±5.52, 70.90±1.16, 54.94±1.01, 80.23±3.39, 61.12±1.39 and 29.55±1.14 μM, respectively) can form the basis for the development of effective therapies against the protozoal tropical disease leishmaniasis.

KEYWORDS:

Anabolic compound; Cunninghamella blakesleeana; Cunninghamella echinulata; Leishmania major; Leishmanicidal activity; Nandrolone

PMID:
25014252
DOI:
10.1016/j.steroids.2014.06.020
[Indexed for MEDLINE]

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