The structure of CP-96, 797, a polyether antibiotic related to K-41 A and produced by Streptomyces sp.

Dirlam, John P.; Bordner, Jon; Cullen, Walter P.; Jefferson, Mark T.; Presseau-Linabury, Laura

doi:10.7164/antibiotics.45.1187

Cited by 14 publications

(13 citation statements)

References 5 publications

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“…In sub-class I , 29 O -glycosylated polyethers were found with variant glycosyl regiospecificity (C5, C6, C15, C18, C22 and C27) including; antibiotics 6016, 1183–1186 A204-A [α-D-amicetose ( 308 )], 1187 carriomycin, 1188,1189 K-41-A, 1190,1191 K-41-B, 1192 X-14868A (maduramicin α), 1193–1196 X-14868C~D, 1193 etheromycin, 1189,1197 >UK-58852, nanhumycin, RP-37454, A80789, CP-120509 [α-D-amicetose ( 308 )], 1198 CP-91243, 1199 CP-91244, 1199 CP-96797, 1200 octacyclomycin, 1201 CP-82009, 1202 semduramicin [α-D-amicetose ( 308 )], 1203 UK-58,852-methylketal, 1204 A-13001-C 1196 and SF-2361, 1205 along with the septamycin analogs. 1206,1207 Of these, β-D-amicetose ( 48a ) was observed in CP-91243 and CP-91244.…”

Section: Polyethersmentioning

confidence: 99%

A comprehensive review of glycosylated bacterial natural products

et al. 2015

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A systematic analysis of all naturally-occurring glycosylated bacterial secondary metabolites reported in the scientific literature up through early 2013 is presented. This comprehensive analysis of 15 940 bacterial natural products revealed 3426 glycosides containing 344 distinct appended carbohydrates and highlights a range of unique opportunities for future biosynthetic study and glycodiversification efforts.

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Section: Polyethersmentioning

confidence: 99%

A comprehensive review of glycosylated bacterial natural products

et al. 2015

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“…K-41A and K-41Am attach a terminal (F) ring [22]. This terminal (F) ring is rare and was only previously found in K-41A, K-41B [22], and CP-96,797 [21]. In this study, we characterised the anti-HIV-1 activity of K-41A and K-41Am as well as the mechanisms involved.…”

Section: Introductionmentioning

confidence: 92%

“…K-41Am is a methylated derivative of K-41A. The only difference between the two compounds is the R substituents [18,21]. The molecular structures of K-41A and K-41Am are shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Polyether antibiotics K-41A and K-41Am inhibit HIV-1 replication via suppressing the activities of HIV-1 reverse transcriptase and integrase

et al. 2020

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Introduction: K-41A is a known compound with antibacterial activity against gram-positive bacteria and coccidia. In our screening of anti-HIV compounds, we found polyether antibiotic K-41A and its analogue K-41Am isolated from a marine-derived Streptomyces sp. SCSIO 01680 exhibited anti-HIV activity. Material and methods: In this study, we characterised the anti-HIV activity of K-41A and K-41Am as well as the mechanism(s) involved. The dose-dependent inhibitory effects of K-41A and K-41Am on HIV-1 replication were observed in the TZM-bl-HIV-1 IIIB system, MT-2-HIV-1 IIIB system, and peripheral blood mononuclear cells (PBMCs)-HIV-1 BaL system. The 50% inhibitory concentrations (IC 50) of K-41A on HIV-1 replication in three systems were 0.75 μM, 0.09 μM, and 0.13 μM, respectively, and the selective indexes (SIs) were 5.81, 49.44, and 598.00, respectively. The IC 50 of K-41Am in three systems were 5.57 μM, 0.24 μM, and 1.15 μM, respectively, and the SIs were > 1.04, 80.71, and > 5.03, respectively. Results: Mechanism research demonstrates that two compounds inhibited the activities of HIV-1 reverse transcriptase (RT) and integrase (IN) in a dose-dependent manner. Molecular docking shows that the docking scores were relatively high between the compound and HIV-1 RT or IN. Conclusions: K-41A and K-41Am possess anti-HIV-1 activity via a multi-target inhibition mechanism, which provides a novel molecular pattern for anti-HIV drug design and structural modification to improve the anti-HIV activity.

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“…ATCC 55028. Crystal structure of the silver salt of this antibiotic was determined by X-ray analysis [92]. …”

Section: Structures and Biological Properties Of Several Ionophoresmentioning

confidence: 99%

“…It afforded anticoccidial activity against Eimeria tenella in chickens at levels between 60 and 90 mg/kg in feed [92]. …”

Section: Structures and Biological Properties Of Several Ionophoresmentioning

confidence: 99%

Structures and Properties of Naturally Occurring Polyether Antibiotics

Rutkowski

Brzeziński

2013

BioMed Research International

104

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Polyether ionophores represent a large group of natural, biologically active substances produced by Streptomyces spp. They are lipid soluble and able to transport metal cations across cell membranes. Several of polyether ionophores are widely used as growth promoters in veterinary. Polyether antibiotics show a broad spectrum of bioactivity ranging from antibacterial, antifungal, antiparasitic, antiviral, and tumour cell cytotoxicity. Recently, it has been shown that some of these compounds are able to selectively kill cancer stem cells and multidrug-resistant cancer cells. Thus, they are recognized as new potential anticancer drugs. The biological activity of polyether ionophores is strictly connected with their molecular structure; therefore, the purpose of this paper is to present an overview of their formula, molecular structure, and properties.

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The structure of CP-96, 797, a polyether antibiotic related to K-41 A and produced by Streptomyces sp.

Cited by 14 publications

References 5 publications

A comprehensive review of glycosylated bacterial natural products

A comprehensive review of glycosylated bacterial natural products

Polyether antibiotics K-41A and K-41Am inhibit HIV-1 replication via suppressing the activities of HIV-1 reverse transcriptase and integrase

Structures and Properties of Naturally Occurring Polyether Antibiotics

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