Literature DB >> 18205372

The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp.

Chambers C Hughes1, Alejandra Prieto-Davo, Paul R Jensen, William Fenical.   

Abstract

Cultivation of an obligate marine Streptomyces strain has furnished the marinopyrroles A and B, densely halogenated, axially chiral metabolites that contain an uncommon bispyrrole structure. X-ray analysis of marinopyrrole B showed that the natural product exists as an atropo-enantiomer with the M-configuration. Though configurationally stable at room temperature, M-(-)-marinopyrrole A can be racemized at elevated temperatures to yield the non-natural P-(+)-atropo-enantiomer. The marinopyrroles possess potent antibiotic activities against methicillin-resistant Staphylococcus aureus.

Entities:  

Mesh:

Substances:

Year:  2008        PMID: 18205372      PMCID: PMC2820876          DOI: 10.1021/ol702952n

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  9 in total

1.  Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora.

Authors:  Robert H Feling; Greg O Buchanan; Tracy J Mincer; Christopher A Kauffman; Paul R Jensen; William Fenical
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-20       Impact factor: 15.336

2.  Statistical approaches for estimating actinobacterial diversity in marine sediments.

Authors:  James E M Stach; Luis A Maldonado; Douglas G Masson; Alan C Ward; Michael Goodfellow; Alan T Bull
Journal:  Appl Environ Microbiol       Date:  2003-10       Impact factor: 4.792

Review 3.  Antibacterial natural products in medicinal chemistry--exodus or revival?

Authors:  Franz von Nussbaum; Michael Brands; Berthold Hinzen; Stefan Weigand; Dieter Häbich
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-04       Impact factor: 15.336

4.  Developing a new resource for drug discovery: marine actinomycete bacteria.

Authors:  William Fenical; Paul R Jensen
Journal:  Nat Chem Biol       Date:  2006-12       Impact factor: 15.040

Review 5.  Natural products as sources of new drugs over the last 25 years.

Authors:  David J Newman; Gordon M Cragg
Journal:  J Nat Prod       Date:  2007-02-20       Impact factor: 4.050

6.  Structure of pyrrolomycin B, a chlorinated nitro-pyrrole antibiotic.

Authors:  M Kaneda; S Nakamura; N Ezaki; Y Iitaka
Journal:  J Antibiot (Tokyo)       Date:  1981-10       Impact factor: 2.649

7.  Antifungal agents. VIII. Synthesis and antifungal activities of bipyrryl analogues of bifonazole.

Authors:  R di Santo; S Massa; R Costi; G Simonetti; A Retico; G Apuzzo; F Troccoli
Journal:  Farmaco       Date:  1994-04

8.  Structure and synthesis of the natural heptachloro-1'-methyl-1,2'-bipyrrole (Q1).

Authors:  Jun Wu; Walter Vetter; Gordon W Gribble; John S Schneekloth; David H Blank; Helmar Görls
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

9.  Pyrrolomycins C, D and E, new members of pyrrolomycins.

Authors:  N Ezaki; M Koyama; T Shomura; T Tsuruoka; S Inouye
Journal:  J Antibiot (Tokyo)       Date:  1983-10       Impact factor: 2.649

  9 in total
  61 in total

1.  Evaluating Nitrogen-Containing Biosynthetic Products Produced by Saltwater Culturing of Several California Littoral Zone Gram-Negative Bacteria.

Authors:  Nicholas Lorig-Roach; Patrick C Still; David Coppage; Jennifer E Compton; Mitchell S Crews; Gabriel Navarro; Karen Tenney; Phillip Crews
Journal:  J Nat Prod       Date:  2017-08-04       Impact factor: 4.050

2.  Discovery of marinopyrrole A (maritoclax) as a selective Mcl-1 antagonist that overcomes ABT-737 resistance by binding to and targeting Mcl-1 for proteasomal degradation.

Authors:  Kenichiro Doi; Rongshi Li; Shen-Shu Sung; Hongwei Wu; Yan Liu; Wanda Manieri; Gowdahalli Krishnegowda; Andy Awwad; Alden Dewey; Xin Liu; Shantu Amin; Chunwei Cheng; Yong Qin; Ernst Schonbrunn; Gary Daughdrill; Thomas P Loughran; Said Sebti; Hong-Gang Wang
Journal:  J Biol Chem       Date:  2012-02-06       Impact factor: 5.157

3.  Total synthesis and biological evaluation of marinopyrrole A and analogues.

Authors:  K C Nicolaou; Nicholas L Simmons; Jason S Chen; Nina M Haste; Victor Nizet
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

4.  Isolation and characterization of potential antibiotic producing actinomycetes from water and sediments of Lake Tana, Ethiopia.

Authors:  Gebreselema Gebreyohannes; Feleke Moges; Samuel Sahile; Nagappan Raja
Journal:  Asian Pac J Trop Biomed       Date:  2013-06

5.  Flavoenzyme-catalyzed atropo-selective N,C-bipyrrole homocoupling in marinopyrrole biosynthesis.

Authors:  Kazuya Yamanaka; Katherine S Ryan; Tobias A M Gulder; Chambers C Hughes; Bradley S Moore
Journal:  J Am Chem Soc       Date:  2012-07-18       Impact factor: 15.419

6.  Maritoclax induces apoptosis in acute myeloid leukemia cells with elevated Mcl-1 expression.

Authors:  Kenichiro Doi; Qiang Liu; Krishne Gowda; Brian M Barth; David Claxton; Shantu Amin; Thomas P Loughran; Hong-Gang Wang
Journal:  Cancer Biol Ther       Date:  2014-05-19       Impact factor: 4.742

7.  Fijiolides A and B, inhibitors of TNF-alpha-induced NFkappaB activation, from a marine-derived sediment bacterium of the genus Nocardiopsis.

Authors:  Sang-Jip Nam; Susana P Gaudêncio; Christopher A Kauffman; Paul R Jensen; Tamara P Kondratyuk; Laura E Marler; John M Pezzuto; William Fenical
Journal:  J Nat Prod       Date:  2010-06-25       Impact factor: 4.050

8.  Activity of the streptogramin antibiotic etamycin against methicillin-resistant Staphylococcus aureus.

Authors:  Nina M Haste; Varahenage R Perera; Katherine N Maloney; Dan N Tran; Paul Jensen; William Fenical; Victor Nizet; Mary E Hensler
Journal:  J Antibiot (Tokyo)       Date:  2010-03-26       Impact factor: 2.649

Review 9.  Novel anti-infective compounds from marine bacteria.

Authors:  Hafizur Rahman; Brian Austin; Wilfrid J Mitchell; Peter C Morris; Derek J Jamieson; David R Adams; Andrew Mearns Spragg; Michael Schweizer
Journal:  Mar Drugs       Date:  2010-03-05       Impact factor: 5.118

10.  Genetic insights into pyralomicin biosynthesis in Nonomuraea spiralis IMC A-0156.

Authors:  Patricia M Flatt; Xiumei Wu; Steven Perry; Taifo Mahmud
Journal:  J Nat Prod       Date:  2013-04-22       Impact factor: 4.050

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.