Cinerubin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00341 |
| CAS | 34044-10-5 |
| Molecular Weight | 827.87 |
| Molecular Formula | C42H53NO16 |
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Description
It is produced by the strain of Streptomyces cinereoruber var. fructo fermentans. Cinerubin A has anti-gram-positive bacteria, mycobacterium, fungis and amoeba activity, and has strong effect on mouse adenocarcinoma E0771.
Specification
| Synonyms | Cinerubine A; Tauromycetin-IV; Antibiotic MA 144A2; Ryemycin-B2 |
| IUPAC Name | methyl (1R,2R,4S)-4-[4-(dimethylamino)-5-[4-hydroxy-6-methyl-5-(6-methyl-5-oxooxan-2-yl)oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate |
| Canonical SMILES | CCC1(CC(C2=C(C3=C(C=C2C1C(=O)OC)C(=O)C4=C(C=CC(=C4C3=O)O)O)O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CCC(=O)C(O7)C)O)N(C)C)O |
| InChI | InChI=1S/C42H53NO16/c1-8-42(52)16-27(31-20(35(42)41(51)53-7)13-21-32(37(31)49)38(50)34-25(46)10-9-24(45)33(34)36(21)48)57-29-14-22(43(5)6)39(18(3)55-29)59-30-15-26(47)40(19(4)56-30)58-28-12-11-23(44)17(2)54-28/h9-10,13,17-19,22,26-30,35,39-40,45-47,49,52H,8,11-12,14-16H2,1-7H3/t17?,18?,19?,22?,26?,27-,28?,29?,30?,35-,39?,40?,42+/m0/s1 |
| InChI Key | STUJMJDONFVTGM-CEPMKHARSA-N |
Properties
| Appearance | Dark Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria; fungi; parasites |
| Melting Point | 155-157 °C |
Reference Reading
1. Glycogenomics as a mass spectrometry-guided genome-mining method for microbial glycosylated molecules
Roland D Kersten, Nadine Ziemert, David J Gonzalez, Brendan M Duggan, Victor Nizet, Pieter C Dorrestein, Bradley S Moore Proc Natl Acad Sci U S A. 2013 Nov 19;110(47):E4407-16. doi: 10.1073/pnas.1315492110. Epub 2013 Nov 4.
Glycosyl groups are an essential mediator of molecular interactions in cells and on cellular surfaces. There are very few methods that directly relate sugar-containing molecules to their biosynthetic machineries. Here, we introduce glycogenomics as an experiment-guided genome-mining approach for fast characterization of glycosylated natural products (GNPs) and their biosynthetic pathways from genome-sequenced microbes by targeting glycosyl groups in microbial metabolomes. Microbial GNPs consist of aglycone and glycosyl structure groups in which the sugar unit(s) are often critical for the GNP's bioactivity, e.g., by promoting binding to a target biomolecule. GNPs are a structurally diverse class of molecules with important pharmaceutical and agrochemical applications. Herein, O- and N-glycosyl groups are characterized in their sugar monomers by tandem mass spectrometry (MS) and matched to corresponding glycosylation genes in secondary metabolic pathways by a MS-glycogenetic code. The associated aglycone biosynthetic genes of the GNP genotype then classify the natural product to further guide structure elucidation. We highlight the glycogenomic strategy by the characterization of several bioactive glycosylated molecules and their gene clusters, including the anticancer agent cinerubin B from Streptomyces sp. SPB74 and an antibiotic, arenimycin B, from Salinispora arenicola CNB-527.
2. Anthracyclines, small-molecule inhibitors of hypoxia-inducible factor-1 alpha activation
Yohko Yamazaki, Yuki Hasebe, Kiyoshi Egawa, Kiyoshi Nose, Setsuko Kunimoto, Daishiro Ikeda Biol Pharm Bull. 2006 Oct;29(10):1999-2003. doi: 10.1248/bpb.29.1999.
Hypoxia-inducible factor-1 (HIF-1) is a central mediator of cellular responses to low oxygen and has recently become an important therapeutic target for solid tumor therapy. To identify small molecule inhibitors of the HIF-1 transcriptional activation, we have established a high through-put assay system using a stable transformant of mammalian cells that express the luciferase reporter gene construct containing a HIF-1 binding site. Using this system, we screened 5000 cultured broths of microorganisms, and we found that cinerubin (1-hydroxy aclacinomycin B) showed a significant inhibition of the reporter activity induced by hypoxic conditions. In addition, we demonstrated that aclarubicin also inhibited the HIF-1 transcriptional activity under hypoxic conditions, but neither doxorubicin nor daunorubicin inhibited it. Consistent with these results, cinerubin and aclarubicin inhibited the hypoxic induction of the vascular endothelial growth factor (VEGF) protein in HepG2 cells, but neither doxorubicin nor daunorubicin affected it. Thus, our results suggested that some anthracyclines are also acting as angiogenesis inhibitors.
3. Actinobacteria from Antarctica as a source for anticancer discovery
Leonardo Jose Silva, Eduardo José Crevelin, Danilo Tosta Souza, Gileno Vieira Lacerda-Júnior, Valeria Maia de Oliveira, Ana Lucia Tasca Gois Ruiz, Luiz Henrique Rosa, Luiz Alberto Beraldo Moraes, Itamar Soares Melo Sci Rep. 2020 Aug 17;10(1):13870. doi: 10.1038/s41598-020-69786-2.
Although many advances have been achieved to treat aggressive tumours, cancer remains a leading cause of death and a public health problem worldwide. Among the main approaches for the discovery of new bioactive agents, the prospect of microbial secondary metabolites represents an effective source for the development of drug leads. In this study, we investigated the actinobacterial diversity associated with an endemic Antarctic species, Deschampsia antarctica, by integrated culture-dependent and culture-independent methods and acknowledged this niche as a reservoir of bioactive strains for the production of antitumour compounds. The 16S rRNA-based analysis showed the predominance of the Actinomycetales order, a well-known group of bioactive metabolite producers belonging to the Actinobacteria phylum. Cultivation techniques were applied, and 72 psychrotolerant Actinobacteria strains belonging to the genera Actinoplanes, Arthrobacter, Kribbella, Mycobacterium, Nocardia, Pilimelia, Pseudarthrobacter, Rhodococcus, Streptacidiphilus, Streptomyces and Tsukamurella were identified. The secondary metabolites were screened, and 17 isolates were identified as promising antitumour compound producers. However, the bio-guided assay showed a pronounced antiproliferative activity for the crude extracts of Streptomyces sp. CMAA 1527 and Streptomyces sp. CMAA 1653. The TGI and LC50 values revealed the potential of these natural products to control the proliferation of breast (MCF-7), glioblastoma (U251), lung/non-small (NCI-H460) and kidney (786-0) human cancer cell lines. Cinerubin B and actinomycin V were the predominant compounds identified in Streptomyces sp. CMAA 1527 and Streptomyces sp. CMAA 1653, respectively. Our results suggest that the rhizosphere of D. antarctica represents a prominent reservoir of bioactive actinobacteria strains and reveals it as an important environment for potential antitumour agents.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
