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Setomimycin Sale

(Synonyms: 昔土米霉素) 目录号 : GC44884

A pre-anthraquinone

Setomimycin Chemical Structure

Cas No.:69431-87-4

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5mg
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产品描述

Setomimycin is a pre-anthraquinone originally isolated from S. pseudovenezuelae. It is active against a variety of Gram-positive bacteria, including S. aureus, B. subtilis, B. cereus, and M. smegmatis (MICs = 1.56-3.13 µg/ml). It also reduces tumor growth in a Sarcoma-180 mouse solid tumor model when administered at a dose of 200 mg/kg per day for seven days.

Chemical Properties

Cas No. 69431-87-4 SDF
别名 昔土米霉素
Canonical SMILES CC(C(C(C)=O)C1=C(C2=C3C(C(CC(C)(O)C3C(C)=O)=O)=C(O)C4=C(O)C=CC=C24)C5=CC=CC(O)=C5C(O)=C16)=CC6=O
分子式 C34H28O9 分子量 580.6
溶解度 Chloroform: soluble,DMSO: soluble 储存条件 Store at -20°C
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1 mM 1.7224 mL 8.6118 mL 17.2236 mL
5 mM 0.3445 mL 1.7224 mL 3.4447 mL
10 mM 0.1722 mL 0.8612 mL 1.7224 mL
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Research Update

Setomimycin as a potential molecule for COVID‑19 target: in silico approach and in vitro validation

Mol Divers 2023 Apr;27(2):619-633.PMID:35622309DOI:10.1007/s11030-022-10441-5.

COVID-19 pandemic caused by the SARS-CoV-2 virus has led to a worldwide crisis. In view of emerging variants time to time, there is a pressing need of effective COVID-19 therapeutics. Setomimycin, a rare tetrahydroanthracene antibiotic, remained unexplored for its therapeutic uses. Herein, we report our investigations on the potential of Setomimycin as COVID-19 therapeutic. Pure Setomimycin was isolated from Streptomyces sp. strain RA-WS2 from NW Himalayan region followed by establishing in silico as well as in vitro anti-SARS-CoV-2 property of the compound against SARS-CoV-2 main protease (Mpro). It was found that the compound targets Mpro enzyme with an IC50 value of 12.02 ± 0.046 μM. The molecular docking study revealed that the compound targets Glu166 residue of Mpro enzyme, hence preventing dimerization of SARS-CoV-2 Mpro monomer. Additionally, the compound also exhibited anti-inflammatory and anti-oxidant property, suggesting that Setomimycin may be a viable option for application against COVID-19 infections.

A new antibiotic, Setomimycin, produced by a strain of Streptomyces

J Antibiot (Tokyo) 1978 Nov;31(11):1091-8.PMID:721705DOI:10.7164/antibiotics.31.1091.

A new antibiotic, Setomimycin, was isolated from the culture broth of strain AM-2947, which was identified as Streptomyces pseudovenezuelae. The compound is a weakly acidic substance, and has UV-absorption at 228, 268 and 422 nm and a molecular formula of C34H28O9 (MW 580). It is active against Gram-positive bacteria including Mycobacteria, and has antitumor activity against Sarcoma-180 solid tumor in mice.

A biostatistical approach for augmenting rare bianthraquinone antibiotic production by Streptomyces sp. RA-WS2 using Taguchi design

AMB Express 2022 Dec 14;12(1):155.PMID:36515787DOI:10.1186/s13568-022-01497-5.

Consistent production of bioactives from microbial sources remains a big challenge for fermentation based bio-processes. Setomimycin, a rare 9,9'-bianthrylanthracene antibiotic reported to be active against Gram positive bacteria i.e. Staphyloccocus aureus, Bacillus subtilis, Bacillus cereus, and Mycobacterium smegmatis, including mycobacteria is one of the least exploited antibiotic. Present work aims to enhance and maximize Setomimycin production using One Factor at a Time (OFAT) approach, followed by Taguchi L9 orthogonal array (OA) design in 30L fermenter. Four most influential parameters, namely carbon source, nitrogen source, air and agitation were selected for optimization studies. The optimized production medium supplemented with 150 g/L glycerol and 7.5 g/L soyabean meal with an agitation rate of 100 RPM and air flow rate of 20 LPM (Liters Per Minute) resulted in 675 mg/L Setomimycin production within 96-108 h of fermentation as compared to the initial production i.e. 40 mg/L. Thus, an overall enhancement of 16.8 folds was achieved in Setomimycin production after optimization in 30L fermenter.

Identification and taxonomy of Streptomyces justiciae strain RA-WS2: a novel Setomimycin producing actinobacterium

3 Biotech 2023 Feb;13(2):47.PMID:PMC9837335DOI:10.1007/s13205-023-03459-5.

The taxonomic position of novel bianthraquinone antibiotic producer Streptomyces strain RA-WS2, a soil isolate from Shivalik region of NW Himalayas, India, has been described. The isolate produces Setomimycin as a major secondary metabolite under defined submerged fermentation conditions. 16S rRNA partial gene sequencing of the isolate indicated its closest similarity (99.4%) with Streptomyces cyaneochromogenes, followed by Streptomyces aquilus. However, the morphological characteristics i.e. colony colour, mycelium and spore chain arrangement were found to be close to Streptomyces aquilus. Therefore, a polyphasic approach was used for taxonomic positioning of the isolate. The Whole genome based similarity with 88.4% dDDH value, 98.65% ANI and 96.99% AAI value indicated its closest identity with Streptomyces justiciae. The taxonomic characteristics such as white colony with smooth surface, cylindrical spores arranged in straight chain, diffusible melanin production, high salt tolerance, 16S rRNA gene sequencing and phylogenomic studies, led to the identification of the strain as Streptomyces justiciae RA-WS2. The predicted biosynthetic gene clusters further confirmed the presence of the BGC for Setomimycin biosynthesis in Streptomyces justiciae strain RA-WS2. Supplementary information: The online version contains supplementary material available at 10.1007/s13205-023-03459-5.

Lincolnenins A-D: Isomeric Bactericidal Bianthracenes from Streptomyces lincolnensis

J Org Chem 2021 Aug 20;86(16):11011-11018.PMID:33320674DOI:10.1021/acs.joc.0c02492.

Cultivation profiling followed by chemical analysis of Streptomyces lincolnensis yielded four new isomeric bianthracenes, lincolnenins A-D (1-4), with relative stereostructures assigned on the basis of detailed spectroscopic analysis. Lincolnenins A (1) and B (2) exhibit restricted rotation about alternate bianthracene 9-9' and 9-8' bridges, respectively, and exist as single atropisomers, whereas C (3) and D (4) are thermally interconvertible atropisomers sharing a common 8-8' bianthracene bridge. Absolute configurations were assigned to 1-4 on the basis of diagnostic ROESY correlations and ECD calculations, whereas acid-mediated dehydration of 1 led to formation and revision of the absolute configuration of the biosynthetically related known Streptomyces antibiotic, Setomimycin (5). Lincolnenin A (1) exhibited significant bactericidal activity against multiple susceptible and drug-resistant Gram-positive pathogens (MIC99 < 2.0 μM), including Mycobacterium tuberculosis H37Ra (MIC99 = 0.9 μM).