A pair of sulfur-containing geldanamycin analogs, 19-S-methylgeldanamycin and 4,5-dihydro- 19-S-methylgeldanamycin, from Streptomyces hygroscopicus 17997

Liu, Xin; Li, Jingyan; Ni, Shibing; Wu, Linzhuan; Wang, Hongyuan; Li, Gang; He, Weiqing; Wang, Yiguang

doi:10.1038/ja.2011.39

Cited by 12 publications

(5 citation statements)

References 27 publications

(9 reference statements)

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“…Therefore, studies on GM analogs have now gained increasing attention. Accordingly, various GM analogs have been developed by chemical modification and by engineered biosynthesis [ 20 ]. Especially, GM and its two semi-synthetic analogs 17-allylaminogeldanamycin (17-AAG) and 17-dimethylaminoethylamino-17-demethoxygeldanamyein (17-DMAG) show a broad spectrum of anticancer activity by inhibiting Hsp90 (Heat shock protein 90) activity [ 21 , 22 ].…”

Section: Introductionmentioning

confidence: 99%

Biological and Chemical Diversity of Bacteria Associated with a Marine Flatworm

Lin

Wang

et al. 2017

Marine Drugs

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The aim of this research is to explore the biological and chemical diversity of bacteria associated with a marine flatworm Paraplanocera sp., and to discover the bioactive metabolites from culturable strains. A total of 141 strains of bacteria including 45 strains of actinomycetes and 96 strains of other bacteria were isolated, identified and fermented on a small scale. Bioactive screening (antibacterial and cytotoxic activities) and chemical screening (ultra-performance liquid chromatography–mass spectrometry (UPLC-MS)) yielded several target bacterial strains. Among these strains, the ethyl acetate (EA) crude extract of Streptomyces sp. XY-FW47 fermentation broth showed strong antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC43300 (MRSA ATCC43300) and potent cytotoxic effects on HeLa cells. The UPLC-MS spectral analysis of the crude extract indicated that the strain XY-FW47 could produce a series of geldanamycins (GMs). One new geldanamycin (GM) analog, 4,5-dihydro-17-O-demethylgeldanamycin (1), and three known GMs (2–4) were obtained. All of these compounds were tested for antibacterial, cytotoxic, and antifungal activities, yet only GM (3) showed potent cytotoxic (HeLa cells, EC50 = 1.12 μg/mL) and antifungal (Setosphaeria turcica MIC = 2.40 μg/mL) activities. Their structure–activity relationship (SAR) was also preliminarily discussed in this study.

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Section: Introductionmentioning

confidence: 99%

Biological and Chemical Diversity of Bacteria Associated with a Marine Flatworm

Lin

Wang

et al. 2017

Marine Drugs

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“…Compound 1 retained potent cytotoxicity against cancer cells, and meanwhile exhibited increased water solubility and photostability compared with GDM. 1 As a methylthio-derivative of GDM, 1's synthetic mechanism in S. hygroscopicus 17997 remains unclear. The biosynthetic pathway of GDM does not contain any methylthiolation reaction.…”

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confidence: 99%

Methanethiol as a catabolite of methionine provides methylthio- group for chemical formation of 19-S-methylgeldanamycin and 17,19-dimethylthioherbimycin A

Cui

Lu³

et al. 2013

J Antibiot

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“…Other geldanamycin-related compounds annotated in our samples ( Table 1 ; Fig. 7 ) have previously been obtained by fermentation of Streptomyces strains ( 72 – 74 ). Two smaller, separate networks also contained geldanamycin-related compounds.…”

Section: Resultsmentioning

confidence: 99%