CP-61,405, a novel polycyclic pyrrolether antibiotic produced byStreptomyces routienii Huang sp. nov.

Cullen, Walter P.; Celmer, Walter D.; Chappel, Larry R.; Huang, Liang H.; Jefferson, Mark T.; Ishiguro, Masaru; Maeda, Hiroshi; Nishiyama, Satoshi; Oscarson, John R.; Shibakawa, Riichiro; Tone, Junsuke

doi:10.1007/bf01569573

Cited by 16 publications

(4 citation statements)

References 10 publications

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“…We proceeded to evaluate the antibacterial efficacy of routiennocin, ent-routiennocin, and the diastereomeric variant 20 against various Gram-positive and Gram-negative bacteria as detailed in Figure 2. Notably, routiennocin exhibited low minimal inhibitory concentration (MIC) against Gram-positive strains consistent with previously reported data, [38] and in line with that of calcimycin albeit with reduced potency. [18] Interestingly, ent-routiennocin exhibited equipotent antimicrobial activity to that of the naturally occurring routiennocin.…”

Section: Resultssupporting

confidence: 90%

“…[35,36] Recently, however, the group of Kozmin reported a concise route to routiennocin in just 8 steps [37] which we found to be an attractive possibility to efficiently access stereoisomers and thereby to probe the unexplored stereochemical influence in the antibiotic family (Figure 1A). Albeit much less studied, routiennocin has been shown to possess antibiotic activity [38] similar to that of calcimycin, although more advanced activities, e. g. inhibition of biofilms, [18] is not known for routiennocin.…”

Section: Resultsmentioning

confidence: 99%

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The Biological Activities of Polyether Ionophore Antibiotic Routiennocin is Independent of Absolute Stereochemistry

Borcher Møller,

Rasmussen,

et al. 2024

ChemBioChem

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Carboxylic polyether ionophores (CPIs) are among the most prevalent agricultural antibiotics (notably in the US) and these compounds have been in use for decades. The potential to reposition CPIs beyond veterinary use, e.g. through chemical modifications to enhance their selectivity window, is an exciting challenge and opportunity, considering their general resilience towards resistance development. Given the very large societal impact of these somewhat controversial compounds, it is surprising that many aspects of their mechanisms and activities in cells remain unclear. Here, we report comparative biological activities of the CPI routiennocin and two stereoisomers, including its enantiomer. We used an efficient convergent synthesis strategy to access the compounds and conducted a broad survey of antibacterial activities against planktonic cells and biofilms as well as the compounds’ effects on mammalian cells, the latter assessed both via standard cell viability assays and broad morphological profiling. Interestingly, similar bioactivity of the enantiomeric pair was observed across all assays, strongly suggesting that chiral interactions do not play a decisive role in the mode of action. Overall, our findings are consistent with a mechanistic model involving highly dynamic behaviour of CPIs in biological membranes.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

The Biological Activities of Polyether Ionophore Antibiotic Routiennocin is Independent of Absolute Stereochemistry

Borcher Møller,

Rasmussen,

et al. 2024

ChemBioChem

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“…Calcimycin (3) is the best characterized one, with relative and absolute configurations established by single-crystal X-ray crystallographic analysis and comparison of the optical rotations for the natural and synthetic [3b] samples. Next to calcimycin is routiennocin (7), the absolute (and consequently, the relative) configuration of which was also secured by comparison of the optical rota-tions for the natural and synthetic [7b,c] samples despite the lack of any X-ray data. X-14885 (6) has only a relative configuration secured by single-crystal X-ray crystallography; its absolute configuration might remain unknown until its optical rotation is determined someday.…”

Section: Introductionmentioning

confidence: 92%

Synthesis and Absolute Configuration of Demethyl (C‐11) Cezomycin

2013

Chemistry An Asian Journal

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The synthesis of (-)-demethyl (C-11) cezomycin was achieved through an efficient route that features the use of a Kulinkovich reaction to couple two multifunctionality-containing fragments and a cascade of ring opening of cyclopropanol/1,5-hydrogen shift/desilylation-oxidation. The hidden yet undeniable problem of irreproducible specific rotation for this family of compounds was solved by sufficient acidification. The absolute configuration for the natural product was thus established as the mirror image of the synthetic sample.

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“…Fermentation of Actinomadura roseorufa Huang sp. nov. ATCC 39697 produces UK-58852 43 together with minor amounts of CP-70228 44 and CP-70828 45 (98,99). Treatment of 43 with para-toluenesulfonic acid in acetonitrile/water yielded a mixture of two compounds, including semduramicin 46.…”

Section: Polyether Glycosidic Ionophoresmentioning

confidence: 99%

Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides

Dembitsky

2005

Lipids

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Polyether glycosidic ionophores and macrocyclic glycosides are of great interest, especially for the medicinal and pharmaceutical industries. These biologically active natural surfactants are good prospects for the future chemical preparation of compounds useful as antibiotics, anticancer agents, or in industry. More than 300 interesting and unusual natural surfactants are described in this review article, including their chemical structures and biological activities.

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CP-61,405, a novel polycyclic pyrrolether antibiotic produced byStreptomyces routienii Huang sp. nov.

Cited by 16 publications

References 10 publications

The Biological Activities of Polyether Ionophore Antibiotic Routiennocin is Independent of Absolute Stereochemistry

The Biological Activities of Polyether Ionophore Antibiotic Routiennocin is Independent of Absolute Stereochemistry

Synthesis and Absolute Configuration of Demethyl (C‐11) Cezomycin

Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides

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