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

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dc.contributor.author Baydoun E.
dc.contributor.author Karam M.
dc.contributor.author Atia-Tul-Wahab
dc.contributor.author Khan M.S.A.
dc.contributor.author Ahmad M.S.
dc.contributor.author Samreen
dc.contributor.author Smith C.
dc.contributor.author Abdel-Massih R.
dc.contributor.author Choudhary M.I.
dc.contributor.editor
dc.date 2014
dc.date.accessioned 2017-10-03T15:43:32Z
dc.date.available 2017-10-03T15:43:32Z
dc.date.issued 2014
dc.identifier 10.1016/j.steroids.2014.06.020
dc.identifier.isbn
dc.identifier.issn
dc.identifier.uri http://hdl.handle.net/10938/12495
dc.description.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, andgt;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. © 2014 Elsevier Inc. All rights reserved.
dc.format.extent
dc.format.extent Pages: (95-100)
dc.language English
dc.publisher Elsevier Inc.; NEW YORK
dc.relation.ispartof Publication Name: Steroids; Publication Year: 2014; Volume: 88; Pages: (95-100);
dc.relation.ispartofseries
dc.relation.uri
dc.source Scopus
dc.subject.other
dc.title Microbial transformation of nandrolone with Cunninghamella echinulata and Cunninghamella blakesleeana and evaluation of leishmaniacidal activity of transformed products
dc.type Article
dc.contributor.affiliation Baydoun, E., Department of Biology, American University of Beirut, Beirut 1107 2020, Lebanon
dc.contributor.affiliation Karam, M., Department of Biology, American University of Beirut, Beirut 1107 2020, Lebanon
dc.contributor.affiliation Atia-Tul-Wahab, Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
dc.contributor.affiliation Khan, M.S.A., H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
dc.contributor.affiliation Ahmad, M.S., H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
dc.contributor.affiliation Samreen, H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
dc.contributor.affiliation Smith, C., Department of Biology, American University of Beirut, Beirut 1107 2020, Lebanon
dc.contributor.affiliation Abdel-Massih, R., Department of Biology, University of Balamand, Koura 100, Lebanon
dc.contributor.affiliation Choudhary, M.I., 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
dc.contributor.authorAddress Baydoun, E.; Department of Biology, American University of Beirut, Beirut 1107 2020, Lebanon; email: eliasbay@aub.edu.lb
dc.contributor.authorCorporate University: American University of Beirut; Faculty: Faculty of Arts and Sciences; Department: Biology;
dc.contributor.authorDepartment Biology
dc.contributor.authorDivision
dc.contributor.authorEmail eliasbay@aub.edu.lb; iqbal.choudhary@iccs.edu
dc.contributor.faculty Faculty of Arts and Sciences
dc.contributor.authorInitials Baydoun, E
dc.contributor.authorInitials Karam, M
dc.contributor.authorInitials Atia-tul-Wahab
dc.contributor.authorInitials Khan, MSA
dc.contributor.authorInitials Ahmad, MS
dc.contributor.authorInitials Samreen
dc.contributor.authorInitials Smith, C
dc.contributor.authorInitials Abdel-Massih, R
dc.contributor.authorInitials Choudhary, MI
dc.contributor.authorOrcidID
dc.contributor.authorReprintAddress Baydoun, E (reprint author), Amer Univ Beirut, Dept Biol, Beirut 11072020, Lebanon.
dc.contributor.authorResearcherID
dc.contributor.authorUniversity American University of Beirut
dc.description.cited Al-Aboudi A, 2009, STEROIDS, V74, P483, DOI 10.1016-j.steroids.2009.01.002; Alarcon J, 2007, J MOL CATAL B-ENZYM, V48, P23, DOI 10.1016-j.molcatb.2007.06.001; Antinarelli Luciana Mr, 2012, Org Med Chem Lett, V2, P16, DOI 10.1186-2191-2858-2-16; Borges KB, 2008, J PHARMACEUT BIOMED, V46, P945, DOI 10.1016-j.jpba.2007.05.018; Borges KB, 2009, TETRAHEDRON-ASYMMETR, V20, P385, DOI 10.1016-j.tetasy.2009.02.009; BORIS A, 1967, STEROIDS, V9, P299, DOI 10.1016-0039-128X(67)90114-6; CASPI E, 1989, J CHEM SOC CHEM COMM, P1699, DOI 10.1039-c39890001699; Choudhary MI, 2010, STEROIDS, V75, P956, DOI 10.1016-j.steroids.2010.05.017; Choudhary MI, 2008, NAT PROD RES, V22, P1289, DOI 10.1080-14786410500462660; Choudhary MI, 2005, CHEM BIODIVERS, V2, P392, DOI 10.1002-cbdv.200590019; Choudhary MI, 2011, STEROIDS, V76, P1288, DOI 10.1016-j.steroids.2011.06.007; Choudhary MI, 2009, STEROIDS, V74, P1040, DOI 10.1016-j.steroids.2009.08.003; Choudhary MI, 2007, STEROIDS, V72, P923, DOI 10.1016-j.steroids.2007.08.002; Choudhary MI, 2012, J ENZYM INHIB MED CH, V27, P348, DOI 10.3109-14756366.2011.590804; de Flines J, 1963, RECL TRAV CHIM PAY B, V82, P129; de Flines J, 1963, RECL TRAV CHIM PAY B, V82, P121; de Flines J, 1963, RECL TRAV CHIM PAY B, V82, P149; Desjeux P, 2004, COMP IMMUNOL MICROB, V27, P305, DOI 10.1016-j.cimid.2004.03.004; Farooq A, 2002, Z NATURFORSCH C, V57, P303; Hazra S, 2013, EXP PARASITOL, V135, P407, DOI 10.1016-j.exppara.2013.07.021; Hernandez-Torres A, 2013, SCAND J INFECT DIS, V45, P567, DOI 10.3109-00365548.2012.752859; Huszcza E, 2003, J BASIC MICROB, V43, P113, DOI 10.1002-jobm.200390011; Kolet SP, 2013, STEROIDS, V78, P1152, DOI 10.1016-j.steroids.2013.08.004; Kouvelas D, 2008, INT J NEUROPSYCHOPH, V11, P925, DOI 10.1017-S1461145708008754; Oliveira-Silva FD, 2008, AM J TROP MED HYG, V78, P745; Parshikov IA, 2000, APPL ENVIRON MICROB, V66, P2664, DOI 10.1128-AEM.66.6.2664-2667.2000; Shao-rui C, 2010, CHEM RES CHINESE U, V26, P922; Yazdi MT, 2006, ARCH PHARM, V339, P473, DOI 10.1002-ardp.200500235
dc.description.citedCount
dc.description.citedTotWOSCount 0
dc.description.citedWOSCount 0
dc.format.extentCount 6
dc.identifier.articleNo
dc.identifier.coden STEDA
dc.identifier.pubmedID
dc.identifier.scopusID 84905181434
dc.identifier.url
dc.publisher.address 360 PARK AVE SOUTH, NEW YORK, NY 10010-1710 USA
dc.relation.ispartofConference
dc.relation.ispartofConferenceCode
dc.relation.ispartofConferenceDate
dc.relation.ispartofConferenceHosting
dc.relation.ispartofConferenceLoc
dc.relation.ispartofConferenceSponsor
dc.relation.ispartofConferenceTitle
dc.relation.ispartofFundingAgency
dc.relation.ispartOfISOAbbr Steroids
dc.relation.ispartOfIssue
dc.relation.ispartOfPart
dc.relation.ispartofPubTitle Steroids
dc.relation.ispartofPubTitleAbbr Steroids
dc.relation.ispartOfSpecialIssue
dc.relation.ispartOfSuppl
dc.relation.ispartOfVolume 88
dc.source.ID WOS:000341549700015
dc.type.publication Journal
dc.subject.otherAuthKeyword Anabolic compound
dc.subject.otherAuthKeyword Cunninghamella blakesleeana
dc.subject.otherAuthKeyword Cunninghamella echinulata
dc.subject.otherAuthKeyword Leishmania major
dc.subject.otherAuthKeyword Leishmanicidal activity
dc.subject.otherAuthKeyword Nandrolone
dc.subject.otherChemCAS nandrolone, 434-22-0
dc.subject.otherIndex 10beta hydroxy 19 nor 4 androsten 3,17 dione
dc.subject.otherIndex 10beta,12beta,17beta trihydroxy 19 nor 4 androsten 3 one
dc.subject.otherIndex 10beta,16alpha,17beta trihydroxy 19 nor 4 androsten 3 one
dc.subject.otherIndex 10beta,17beta dihydroxy 19 nor 4 androsten 3 one
dc.subject.otherIndex 16beta,17beta dihydroxy 19 nor 4 androsten 3 one
dc.subject.otherIndex 6beta,10beta,17beta trihydroxy 19 nor 4 androsten 3 one
dc.subject.otherIndex 6beta,17beta dihydroxy 19 nor 4 androsten 3 one
dc.subject.otherIndex antileishmanial agent
dc.subject.otherIndex drug metabolite
dc.subject.otherIndex nandrolone
dc.subject.otherIndex unclassified drug
dc.subject.otherIndex antileishmanial activity
dc.subject.otherIndex article
dc.subject.otherIndex biotransformation
dc.subject.otherIndex carbon nuclear magnetic resonance
dc.subject.otherIndex Cunninghamella blakesleeana
dc.subject.otherIndex Cunninghamella echinulata
dc.subject.otherIndex drug activity
dc.subject.otherIndex drug synthesis
dc.subject.otherIndex fermentation
dc.subject.otherIndex in vitro study
dc.subject.otherIndex Leishmania major
dc.subject.otherIndex leishmaniasis
dc.subject.otherIndex nonhuman
dc.subject.otherIndex proton nuclear magnetic resonance
dc.subject.otherKeywordPlus ANABOLIC-STEROIDS
dc.subject.otherKeywordPlus BIOTRANSFORMATION
dc.subject.otherKeywordPlus FUNGI
dc.subject.otherKeywordPlus ELEGANS
dc.subject.otherWOS Biochemistry and Molecular Biology
dc.subject.otherWOS Endocrinology and Metabolism


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