Cosmomycin D
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| Category | Antibiotics |
| Catalog number | BBF-03036 |
| CAS | 95676-81-6 |
| Molecular Weight | 1189.34 |
| Molecular Formula | C60H88N2O22 |
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Description
It is an anthracycline antibiotic produced by the strain of Streptomyces cyaneus (A-447). It has anti-tumor activity. It can inhibit the growth of P388 murine lymphocytic leukemia cells.
Specification
| Synonyms | (3''S,3'''''S)-3'',3'''''-Dihydroxycytorhodin A; 1-Deoxyobelmycin D; 3B,3E-Dihydroxycytorhodin A; A-447A; Antibiotic A-447A; 5,12-Naphthacenedione, 8-ethyl-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-7,10-bis((2,3,6-trideoxy-4-O-(2,6-dideoxy-4-O-((2S,5S,6S)-tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)-, (7R,8R,10S)- |
| IUPAC Name | (7S,9R,10R)-7,10-bis[[(2S,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-5-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy]-9-ethyl-4,6,9,11-tetrahydroxy-8,10-dihydro-7H-tetracene-5,12-dione |
| Canonical SMILES | CCC1(CC(C2=C(C1OC3CC(C(C(O3)C)OC4CC(C(C(O4)C)OC5CCC(C(O5)C)O)O)N(C)C)C(=C6C(=C2O)C(=O)C7=C(C6=O)C=CC=C7O)O)OC8CC(C(C(O8)C)OC9CC(C(C(O9)C)OC1CCC(C(O1)C)O)O)N(C)C)O |
| InChI | InChI=1S/C60H88N2O22/c1-12-60(72)24-39(79-42-20-32(61(8)9)55(27(4)75-42)82-44-22-37(66)57(29(6)77-44)80-40-18-16-34(63)25(2)73-40)47-50(54(71)48-49(53(47)70)52(69)46-31(51(48)68)14-13-15-36(46)65)59(60)84-43-21-33(62(10)11)56(28(5)76-43)83-45-23-38(67)58(30(7)78-45)81-41-19-17-35(64)26(3)74-41/h13-15,25-30,32-35,37-45,55-59,63-67,70-72H,12,16-24H2,1-11H3/t25-,26-,27-,28-,29-,30-,32-,33-,34-,35-,37-,38-,39-,40-,41-,42-,43-,44-,45-,55+,56+,57+,58+,59+,60+/m0/s1 |
| InChI Key | DKWBRHNUUTWKAG-JNZMSYBZSA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Melting Point | 188-191°C |
| Density | 1.42 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Chemical entrapment and killing of insects by bacteria
Louis K Ho, Martin Daniel-Ivad, Swathi P Jeedigunta, Jing Li, Konstantin G Iliadi, Gabrielle L Boulianne, Thomas R Hurd, Craig A Smibert, Justin R Nodwell Nat Commun. 2020 Sep 14;11(1):4608. doi: 10.1038/s41467-020-18462-0.
Actinobacteria produce antibacterial and antifungal specialized metabolites. Many insects harbour actinobacteria on their bodies or in their nests and use these metabolites for protection. However, some actinobacteria produce metabolites that are toxic to insects and the evolutionary relevance of this toxicity is unknown. Here we explore chemical interactions between streptomycetes and the fruit fly Drosophila melanogaster. We find that many streptomycetes produce specialized metabolites that have potent larvicidal effects against the fly; larvae that ingest spores of these species die. The mechanism of toxicity is specific to the bacterium's chemical arsenal: cosmomycin D producing bacteria induce a cell death-like response in the larval digestive tract; avermectin producing bacteria induce paralysis. Furthermore, low concentrations of volatile terpenes like 2-methylisoborneol that are produced by streptomycetes attract fruit flies such that they preferentially deposit their eggs on contaminated food sources. The resulting larvae are killed during growth and development. The phenomenon of volatile-mediated attraction and specialized metabolite toxicity suggests that some streptomycetes pose an evolutionary risk to insects in nature.
2. Mycothiol Peroxidase Activity as a Part of the Self-Resistance Mechanisms against the Antitumor Antibiotic Cosmomycin D
Roger D Castillo Arteaga, Leandro M Garrido, Brandán Pedre, Irina Helmle, Harald Gross, Bertolt Gust, Gabriel Padilla Microbiol Spectr. 2022 Jun 29;10(3):e0049322. doi: 10.1128/spectrum.00493-22. Epub 2022 May 5.
Antibiotic-producing microorganisms usually require one or more self-resistance determinants to survive antibiotic production. The effectors of these mechanisms are proteins that inactivate the antibiotic, facilitate its transport, or modify the target to render it insensitive to the molecule. Streptomyces bacteria biosynthesize various bioactive natural products and possess resistance systems for most metabolites, which are coregulated with antibiotic biosynthesis genes. Streptomyces olindensis strain DAUFPE 5622 produces the antitumor antibiotic cosmomycin D (COSD), a member of the anthracycline family. In this study, we propose three self-resistance mechanisms, anchored or based in the COSD biosynthetic gene cluster. These include cosIJ (an ABC transporter), cosU (a UvrA class IIa protein), and a new self-resistance mechanism encoded by cosP, which shows response against peroxides by the enzyme mycothiol peroxidase (MPx). Activity-based investigations of MPx and its mutant enzyme confirmed peroxidation during the production of COSD. Overexpression of the ABC transporter, the UvrA class IIa protein, and the MPx led to an effective response against toxic anthracyclines, such as cosmomycins. Our findings help to understand how thiol peroxidases play an antioxidant role in the anthracycline producer S. olindensis DAUFPE 5622, a mechanism which has been reported for neoplastic cells that are resistant to doxorubicin (DOX). IMPORTANCE Anthracycline compounds are DNA intercalating agents widely used in cancer chemotherapeutic protocols. This work focused on the self-resistance mechanisms developed by the cosmomycin-producing bacterium Streptomyces olindensis. Our findings showed that cysteine peroxidases, such as mycothiol peroxidase, encoded by the gene cosP, protected S. olindensis against peroxidation during cosmomycin production. This observation can contribute to much better understanding of resistance both in the producers, eventually enhancing production, and in some tumoral cell lines.
3. Genome Sequence of Streptomyces olindensis DAUFPE 5622, Producer of the Antitumoral Anthracycline Cosmomycin D
Juan D Rojas, Antonio Starcevic, Damir Baranas̆ić, Maria A Ferreira-Torres, Camilo A Contreras, Leandro M Garrido, Welington L Araújo, Robson F de Souza, Jurica Zucko, Daslav Hranueli, Paul F Long, John Cullum, Gabriel Padilla Genome Announc. 2014 Jun 26;2(3):e00541-14. doi: 10.1128/genomeA.00541-14.
Streptomyces olindensis DAUFPE 5622, which was isolated from a Brazilian soil sample, produces the antitumor anthracycline cosmomycin D. The genome sequence is 9.4 Mb in length, with a G+C content of 71%. Thirty-four putative secondary metabolite biosynthetic gene clusters were identified, including the cosmomycin D cluster.
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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 ╳
