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Volumn 99, Issue 16, 2015, Pages 6745-6752

Engineered biosynthesis of pimaricin derivatives with improved antifungal activity and reduced cytotoxicity

Author keywords

Antifungal activity; Cytotoxicity; Pimaricin; Polyene macrolide; Streptomyces

Indexed keywords

BACTERIA; BIOCHEMISTRY; CYTOTOXICITY; FUNGI; GENETIC ENGINEERING;

EID: 84937972288     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-015-6635-9     Document Type: Article
Times cited : (23)

References (32)
  • 1
    • 1942539982 scopus 로고    scopus 로고
    • Identification of PimR as a positive regulator of pimaricin biosynthesis in Streptomyces natalensis
    • COI: 1:CAS:528:DC%2BD2cXjsFKrtrs%3D, PID: 15090496
    • Anton N, Mendes MV, Martin JF, Aparicio JF (2004) Identification of PimR as a positive regulator of pimaricin biosynthesis in Streptomyces natalensis. J Bacteriol 186(9):2567–2575
    • (2004) J Bacteriol , vol.186 , Issue.9 , pp. 2567-2575
    • Anton, N.1    Mendes, M.V.2    Martin, J.F.3    Aparicio, J.F.4
  • 2
    • 34948839957 scopus 로고    scopus 로고
    • PimM, a PAS domain positive regulator of pimaricin biosynthesis in Streptomyces natalensis
    • COI: 1:CAS:528:DC%2BD2sXhtFKrtLzO, PID: 17768260
    • Anton N, Santos-Aberturas J, Mendes MV, Guerra SM, Martin JF, Aparicio JF (2007) PimM, a PAS domain positive regulator of pimaricin biosynthesis in Streptomyces natalensis. Microbiology 153(Pt 9):3174–3183
    • (2007) Microbiology , vol.153 , pp. 3174-3183
    • Anton, N.1    Santos-Aberturas, J.2    Mendes, M.V.3    Guerra, S.M.4    Martin, J.F.5    Aparicio, J.F.6
  • 3
    • 0033537959 scopus 로고    scopus 로고
    • The biosynthetic gene cluster for the 26-membered ring polyene macrolide pimaricin. A new polyketide synthase organization encoded by two subclusters separated by functionalization genes
    • COI: 1:CAS:528:DyaK1MXis1Gjt7o%3D, PID: 10187796
    • Aparicio JF, Colina AJ, Ceballos E, Martin JF (1999) The biosynthetic gene cluster for the 26-membered ring polyene macrolide pimaricin. A new polyketide synthase organization encoded by two subclusters separated by functionalization genes. J Biol Chem 274(15):10133–10139
    • (1999) J Biol Chem , vol.274 , Issue.15 , pp. 10133-10139
    • Aparicio, J.F.1    Colina, A.J.2    Ceballos, E.3    Martin, J.F.4
  • 4
    • 0033763409 scopus 로고    scopus 로고
    • A complex multienzyme system encoded by five polyketide synthase genes is involved in the biosynthesis of the 26-membered polyene macrolide pimaricin in Streptomyces natalensis
    • COI: 1:CAS:528:DC%2BD3cXosVWitLo%3D, PID: 11094342
    • Aparicio JF, Fouces R, Mendes MV, Olivera N, Martin JF (2000) A complex multienzyme system encoded by five polyketide synthase genes is involved in the biosynthesis of the 26-membered polyene macrolide pimaricin in Streptomyces natalensis. Chem Biol 7(11):895–905
    • (2000) Chem Biol , vol.7 , Issue.11 , pp. 895-905
    • Aparicio, J.F.1    Fouces, R.2    Mendes, M.V.3    Olivera, N.4    Martin, J.F.5
  • 5
    • 0344291484 scopus 로고    scopus 로고
    • Comparative molecular dynamics simulations of amphotericin B-cholesterol/ergosterol membrane channels
    • COI: 1:CAS:528:DC%2BD38XpsFWjsbs%3D, PID: 12488039
    • Baginski M, Resat H, Borowski E (2002) Comparative molecular dynamics simulations of amphotericin B-cholesterol/ergosterol membrane channels. Biochim Biophys Acta 1567(1–2):63–78
    • (2002) Biochim Biophys Acta , vol.1567 , Issue.1-2 , pp. 63-78
    • Baginski, M.1    Resat, H.2    Borowski, E.3
  • 6
    • 33646112405 scopus 로고    scopus 로고
    • Probing the structure-function relationship of polyene macrolides: engineered biosynthesis of soluble nystatin analogues
    • COI: 1:CAS:528:DC%2BD28XislCjs78%3D, PID: 16610786
    • Borgos SE, Tsan P, Sletta H, Ellingsen TE, Lancelin JM, Zotchev SB (2006) Probing the structure-function relationship of polyene macrolides: engineered biosynthesis of soluble nystatin analogues. J Med Chem 49(8):2431–2439
    • (2006) J Med Chem , vol.49 , Issue.8 , pp. 2431-2439
    • Borgos, S.E.1    Tsan, P.2    Sletta, H.3    Ellingsen, T.E.4    Lancelin, J.M.5    Zotchev, S.B.6
  • 7
    • 0034047123 scopus 로고    scopus 로고
    • Biosynthesis of the polyene antifungal antibiotic nystatin in Streptomyces noursei ATCC 11455: analysis of the gene cluster and deduction of the biosynthetic pathway
    • COI: 1:CAS:528:DC%2BD3cXktl2nsLk%3D, PID: 10873841
    • Brautaset T, Sekurova ON, Sletta H, Ellingsen TE, StrLm AR, Valla S, Zotchev SB (2000) Biosynthesis of the polyene antifungal antibiotic nystatin in Streptomyces noursei ATCC 11455: analysis of the gene cluster and deduction of the biosynthetic pathway. Chem Biol 7(6):395–403
    • (2000) Chem Biol , vol.7 , Issue.6 , pp. 395-403
    • Brautaset, T.1    Sekurova, O.N.2    Sletta, H.3    Ellingsen, T.E.4    StrLm, A.R.5    Valla, S.6    Zotchev, S.B.7
  • 9
    • 0034930476 scopus 로고    scopus 로고
    • Amphotericin biosynthesis in Streptomyces nodosus: deductions from analysis of polyketide synthase and late genes
    • COI: 1:CAS:528:DC%2BD3MXltVGju7s%3D, PID: 11451671
    • Caffrey P, Lynch S, Flood E, Finnan S, Oliynyk M (2001) Amphotericin biosynthesis in Streptomyces nodosus: deductions from analysis of polyketide synthase and late genes. Chem Biol 8(7):713–723
    • (2001) Chem Biol , vol.8 , Issue.7 , pp. 713-723
    • Caffrey, P.1    Lynch, S.2    Flood, E.3    Finnan, S.4    Oliynyk, M.5
  • 10
    • 35448963399 scopus 로고    scopus 로고
    • Candida albicans drug resistance another way to cope with stress
    • COI: 1:CAS:528:DC%2BD2sXht1Smur3L, PID: 17906120
    • Cannon RD, Lamping E, Holmes AR, Niimi K, Tanabe K, Niimi M, Monk BC (2007) Candida albicans drug resistance another way to cope with stress. Microbiology 153(Pt 10):3211–3217
    • (2007) Microbiology , vol.153 , pp. 3211-3217
    • Cannon, R.D.1    Lamping, E.2    Holmes, A.R.3    Niimi, K.4    Tanabe, K.5    Niimi, M.6    Monk, B.C.7
  • 11
    • 26944438216 scopus 로고    scopus 로고
    • Biosynthesis of amphotericin derivatives lacking exocyclic carboxyl groups
    • COI: 1:CAS:528:DC%2BD2MXhtVylu7bP, PID: 16079135
    • Carmody M, Murphy B, Byrne B, Power P, Rai D, Rawlings B, Caffrey P (2005) Biosynthesis of amphotericin derivatives lacking exocyclic carboxyl groups. J Biol Chem 280(41):34420–34426
    • (2005) J Biol Chem , vol.280 , Issue.41 , pp. 34420-34426
    • Carmody, M.1    Murphy, B.2    Byrne, B.3    Power, P.4    Rai, D.5    Rawlings, B.6    Caffrey, P.7
  • 12
    • 0345531148 scopus 로고    scopus 로고
    • Organizational and mutational analysis of a complete FR-008/candicidin gene cluster encoding a structurally related polyene complex
    • COI: 1:CAS:528:DC%2BD3sXptlylu7Y%3D, PID: 14652074
    • Chen S, Huang X, Zhou X, Bai L, He J, Jeong KJ, Lee SY, Deng Z (2003) Organizational and mutational analysis of a complete FR-008/candicidin gene cluster encoding a structurally related polyene complex. Chem Biol 10(11):1065–1076
    • (2003) Chem Biol , vol.10 , Issue.11 , pp. 1065-1076
    • Chen, S.1    Huang, X.2    Zhou, X.3    Bai, L.4    He, J.5    Jeong, K.J.6    Lee, S.Y.7    Deng, Z.8
  • 14
    • 84884179896 scopus 로고    scopus 로고
    • Engineered biosynthesis of disaccharide-modified polyene macrolides
    • PID: 23913424
    • De Poire E, Stephens N, Rawlings B, Caffrey P (2013) Engineered biosynthesis of disaccharide-modified polyene macrolides. Appl Environ Microbiol 79(19):6156–6159
    • (2013) Appl Environ Microbiol , vol.79 , Issue.19 , pp. 6156-6159
    • De Poire, E.1    Stephens, N.2    Rawlings, B.3    Caffrey, P.4
  • 15
    • 70350146663 scopus 로고    scopus 로고
    • Identification of a novel Streptomyces chattanoogensis L10 and enhancing its natamycin production by overexpressing positive regulator ScnRII
    • COI: 1:CAS:528:DC%2BD1MXhtFCntr7L, PID: 19763427
    • Du YL, Chen SF, Cheng LY, Shen XL, Tian Y, Li YQ (2009) Identification of a novel Streptomyces chattanoogensis L10 and enhancing its natamycin production by overexpressing positive regulator ScnRII. J Microbiol 47(4):506–513
    • (2009) J Microbiol , vol.47 , Issue.4 , pp. 506-513
    • Du, Y.L.1    Chen, S.F.2    Cheng, L.Y.3    Shen, X.L.4    Tian, Y.5    Li, Y.Q.6
  • 16
    • 79955781112 scopus 로고    scopus 로고
    • The pleiotropic regulator AdpAch is required for natamycin biosynthesis and morphological differentiation in Streptomyces chattanoogensis
    • COI: 1:CAS:528:DC%2BC3MXmvFGgt7s%3D, PID: 21330439
    • Du YL, Li SZ, Zhou Z, Chen SF, Fan WM, Li YQ (2011) The pleiotropic regulator AdpAch is required for natamycin biosynthesis and morphological differentiation in Streptomyces chattanoogensis. Microbiology 157(Pt 5):1300–1311
    • (2011) Microbiology , vol.157 , pp. 1300-1311
    • Du, Y.L.1    Li, S.Z.2    Zhou, Z.3    Chen, S.F.4    Fan, W.M.5    Li, Y.Q.6
  • 17
    • 0030033020 scopus 로고    scopus 로고
    • Antifungal agents: chemotherapeutic targets and immunologic strategies
    • COI: 1:CAS:528:DyaK28Xos1WntQ%3D%3D, PID: 8834867
    • Georgopapadakou NH, Walsh TJ (1996) Antifungal agents: chemotherapeutic targets and immunologic strategies. Antimicrob Agents Chemother 40(2):279–291
    • (1996) Antimicrob Agents Chemother , vol.40 , Issue.2 , pp. 279-291
    • Georgopapadakou, N.H.1    Walsh, T.J.2
  • 18
    • 77049115002 scopus 로고    scopus 로고
    • Redesign of polyene macrolide glycosylation: engineered biosynthesis of 19-O-perosaminyl-amphoteronolide B
    • COI: 1:CAS:528:DC%2BC3cXis1WksL4%3D, PID: 20189107
    • Hutchinson E, Murphy B, Dunne T, Breen C, Rawlings B, Caffrey P (2010) Redesign of polyene macrolide glycosylation: engineered biosynthesis of 19-O-perosaminyl-amphoteronolide B. Chem Biol 17(2):174–182
    • (2010) Chem Biol , vol.17 , Issue.2 , pp. 174-182
    • Hutchinson, E.1    Murphy, B.2    Dunne, T.3    Breen, C.4    Rawlings, B.5    Caffrey, P.6
  • 19
    • 77956013893 scopus 로고    scopus 로고
    • Structure of cytochrome P450 PimD suggests epoxidation of the polyene macrolide pimaricin occurs via a hydroperoxoferric intermediate
    • COI: 1:CAS:528:DC%2BC3cXhtV2iu7bN, PID: 20797613
    • Kells PM, Ouellet H, Santos-Aberturas J, Aparicio JF, Podust LM (2010) Structure of cytochrome P450 PimD suggests epoxidation of the polyene macrolide pimaricin occurs via a hydroperoxoferric intermediate. Chem Biol 17(8):841–851
    • (2010) Chem Biol , vol.17 , Issue.8 , pp. 841-851
    • Kells, P.M.1    Ouellet, H.2    Santos-Aberturas, J.3    Aparicio, J.F.4    Podust, L.M.5
  • 20
    • 0026631602 scopus 로고
    • Structures of amphotericin B-cholesterol complex
    • COI: 1:CAS:528:DyaK38XmsVOhsL0%3D, PID: 1637836
    • Khutorsky VE (1992) Structures of amphotericin B-cholesterol complex. Biochim Biophys Acta 1108(2):123–127
    • (1992) Biochim Biophys Acta , vol.1108 , Issue.2 , pp. 123-127
    • Khutorsky, V.E.1
  • 21
    • 84937984723 scopus 로고    scopus 로고
    • Kieser T, Bibb MJ, Buttner MJ, Charter KF, Hopwood DA (2000) Practical Streptomyces Genetics. The John Innes Foundation, Norwich, United Kingdom
    • Kieser T, Bibb MJ, Buttner MJ, Charter KF, Hopwood DA (eds)(2000) Practical Streptomyces Genetics. The John Innes Foundation, Norwich, United Kingdom
  • 22
    • 2642544178 scopus 로고    scopus 로고
    • An amphotericin B-ergosterol covalent conjugate with powerful membrane permeabilizing activity
    • COI: 1:CAS:528:DC%2BD2cXktF2qsrw%3D, PID: 15157878
    • Matsumori N, Eiraku N, Matsuoka S, Oishi T, Murata M, Aoki T, Ide T (2004) An amphotericin B-ergosterol covalent conjugate with powerful membrane permeabilizing activity. Chem Biol 11(5):673–679
    • (2004) Chem Biol , vol.11 , Issue.5 , pp. 673-679
    • Matsumori, N.1    Eiraku, N.2    Matsuoka, S.3    Oishi, T.4    Murata, M.5    Aoki, T.6    Ide, T.7
  • 23
    • 0034945645 scopus 로고    scopus 로고
    • Engineered biosynthesis of novel polyenes: a pimaricin derivative produced by targeted gene disruption in Streptomyces natalensis
    • COI: 1:CAS:528:DC%2BD3MXltVGjurc%3D, PID: 11451665
    • Mendes MV, Recio E, Fouces R, Luiten R, Martin JF, Aparicio JF (2001) Engineered biosynthesis of novel polyenes: a pimaricin derivative produced by targeted gene disruption in Streptomyces natalensis. Chem Biol 8(7):635–644
    • (2001) Chem Biol , vol.8 , Issue.7 , pp. 635-644
    • Mendes, M.V.1    Recio, E.2    Fouces, R.3    Luiten, R.4    Martin, J.F.5    Aparicio, J.F.6
  • 24
    • 33847661977 scopus 로고    scopus 로고
    • The two-component phoR-phoP system of Streptomyces natalensis: inactivation or deletion of phoP reduces the negative phosphate regulation of pimaricin biosynthesis
    • COI: 1:CAS:528:DC%2BD2sXhvVyktbY%3D, PID: 17142079
    • Mendes MV, Tunca S, Anton N, Recio E, Sola-Landa A, Aparicio JF, Martin JF (2007) The two-component phoR-phoP system of Streptomyces natalensis: inactivation or deletion of phoP reduces the negative phosphate regulation of pimaricin biosynthesis. Metab Eng 9(2):217–227
    • (2007) Metab Eng , vol.9 , Issue.2 , pp. 217-227
    • Mendes, M.V.1    Tunca, S.2    Anton, N.3    Recio, E.4    Sola-Landa, A.5    Aparicio, J.F.6    Martin, J.F.7
  • 26
    • 36649001177 scopus 로고    scopus 로고
    • Analysis of the mycosamine biosynthesis and attachment genes in the nystatin biosynthetic gene cluster of Streptomyces noursei ATCC 11455
    • COI: 1:CAS:528:DC%2BD1cXnsFygsw%3D%3D, PID: 17905880
    • Nedal A, Sletta H, Brautaset T, Borgos SE, Sekurova ON, Ellingsen TE, Zotchev SB (2007) Analysis of the mycosamine biosynthesis and attachment genes in the nystatin biosynthetic gene cluster of Streptomyces noursei ATCC 11455. Appl Environ Microbiol 73(22):7400–7407
    • (2007) Appl Environ Microbiol , vol.73 , Issue.22 , pp. 7400-7407
    • Nedal, A.1    Sletta, H.2    Brautaset, T.3    Borgos, S.E.4    Sekurova, O.N.5    Ellingsen, T.E.6    Zotchev, S.B.7
  • 27
    • 33646475260 scopus 로고    scopus 로고
    • Significant improvement of antifungal activity of polyene macrolides by bisalkylation of the mycosamine
    • COI: 1:CAS:528:DC%2BD28XivVOktbY%3D, PID: 16623556
    • Paquet V, Carreira EM (2006) Significant improvement of antifungal activity of polyene macrolides by bisalkylation of the mycosamine. Org Lett 8(9):1807–1809
    • (2006) Org Lett , vol.8 , Issue.9 , pp. 1807-1809
    • Paquet, V.1    Carreira, E.M.2
  • 28
    • 33749649554 scopus 로고    scopus 로고
    • Glycerol, ethylene glycol and propanediol elicit pimaricin biosynthesis in the PI-factor-defective strain Streptomyces natalensis npi287 and increase polyene production in several wild-type actinomycetes
    • COI: 1:CAS:528:DC%2BD28XhtFWqtb3O, PID: 17005993
    • Recio E, Aparicio JF, Rumbero A, Martin JF (2006) Glycerol, ethylene glycol and propanediol elicit pimaricin biosynthesis in the PI-factor-defective strain Streptomyces natalensis npi287 and increase polyene production in several wild-type actinomycetes. Microbiology 152(Pt 10):3147–3156
    • (2006) Microbiology , vol.152 , pp. 3147-3156
    • Recio, E.1    Aparicio, J.F.2    Rumbero, A.3    Martin, J.F.4
  • 29
    • 34248679167 scopus 로고    scopus 로고
    • Tricine-SDS-PAGE
    • PID: 17406207
    • Schagger H (2006) Tricine-SDS-PAGE. Nat Protoc 1(1):16–22
    • (2006) Nat Protoc , vol.1 , Issue.1 , pp. 16-22
    • Schagger, H.1
  • 30
    • 19544389326 scopus 로고    scopus 로고
    • Two polyene amides produced by genetically modified Streptomyces diastaticus var. 108
    • COI: 1:CAS:528:DC%2BD2MXks1aku7s%3D, PID: 15911374
    • Seco EM, Cuesta T, Fotso S, Laatsch H, Malpartida F (2005) Two polyene amides produced by genetically modified Streptomyces diastaticus var. 108. Chem Biol 12(5):535–543
    • (2005) Chem Biol , vol.12 , Issue.5 , pp. 535-543
    • Seco, E.M.1    Cuesta, T.2    Fotso, S.3    Laatsch, H.4    Malpartida, F.5
  • 31
    • 84878807373 scopus 로고    scopus 로고
    • Versatility of enzymes catalyzing late steps in polyene 67-121C biosynthesis
    • COI: 1:CAS:528:DC%2BC3sXnsV2mu7k%3D, PID: 23563553
    • Stephens N, Rawlings B, Caffrey P (2013) Versatility of enzymes catalyzing late steps in polyene 67-121C biosynthesis. Biosci Biotechnol Biochem 77(4):880–883
    • (2013) Biosci Biotechnol Biochem , vol.77 , Issue.4 , pp. 880-883
    • Stephens, N.1    Rawlings, B.2    Caffrey, P.3
  • 32
    • 84925488983 scopus 로고    scopus 로고
    • Transcriptome-guided identification of SprA as a pleiotropic regulator in Streptomyces chattanoogensis
    • COI: 1:CAS:528:DC%2BC2cXhsl2gtr%2FN, PID: 25326777
    • Zhou ZX, Xu QQ, Bu QT, Liu SP, Yu P, Li YQ (2015) Transcriptome-guided identification of SprA as a pleiotropic regulator in Streptomyces chattanoogensis. Appl Microbiol Biotechnol 99(3):1287–1298
    • (2015) Appl Microbiol Biotechnol , vol.99 , Issue.3 , pp. 1287-1298
    • Zhou, Z.X.1    Xu, Q.Q.2    Bu, Q.T.3    Liu, S.P.4    Yu, P.5    Li, Y.Q.6


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