Collismycin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01731 |
| CAS | 158792-24-6 |
| Molecular Weight | 275.33 |
| Molecular Formula | C13H13N3O2S |
| Purity | ≥ 95% |
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Description
It is produced by the strain of Streptomyces sp. MQ22. It has the inhibitory effect of dexamethasone-glucocorticoid receptor. IC50 is 1.5 X 10-5 mol/L (rat liver cytosol). It has the anti-tumor cell activity, inhibits rat leukemia cell L1210 with IC50 of 0.08 μg/mL.
Specification
| Synonyms | (E)-4-Methoxy-5-(methylthio)-[2,2'-bipyridine]-6-carbaldehyde oxime; (2E)-4-methoxy-3-methylsulfanyl-2-(nitrosomethylidene)-6-pyridin-2-yl-1H-pyridine |
| Storage | -20 °C |
| IUPAC Name | (NE)-N-[(4-methoxy-3-methylsulfanyl-6-pyridin-2-ylpyridin-2-yl)methylidene]hydroxylamine |
| Canonical SMILES | COC1=CC(=NC(=C1SC)C=NO)C2=CC=CC=N2 |
| InChI | InChI=1S/C13H13N3O2S/c1-18-12-7-10(9-5-3-4-6-14-9)16-11(8-15-17)13(12)19-2/h3-8,17H,1-2H3/b15-8+ |
| InChI Key | NQGMIPUYCWIEAW-OVCLIPMQSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 381.2 °C at 760 mmHg |
| Melting Point | 170-172 °C (dec.) |
| Density | 1.27±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol, Ethanol, DMF, DMSO |
Reference Reading
1. The complete genome sequence of Streptomyces albolongus YIM 101047, the producer of novel bafilomycins and odoriferous sesquiterpenoids
Tao Lu, Li Han, Guiding Li, Chenglin Jiang, Min Yin, Yi Jiang, Xueshi Huang J Biotechnol . 2017 Nov 20;262:89-93. doi: 10.1016/j.jbiotec.2017.09.018.
Streptomyces albolongus YIM 101047 produces novel bafilomycins and odoriferous sesquiterpenoids with cytotoxic and antimicrobial activities. Here, we report the complete genome sequence of S. albolongus YIM 101047, which consists of an 8,027,788bp linear chromosome. Forty-six putative biosynthetic gene clusters of secondary metabolites were found. The sesquiterpenoid gene cluster was on the left arm (0.09-0.10Mb), and the bafilomycin biosynthetic gene cluster was on the right arm (7.46-7.64Mb) of the chromosome. Twenty-two putative gene clusters with high or moderate similarity to important antibiotic biosynthetic gene clusters were found, including the antitumor agents bafilomycin, epothilone and hedamycin; the antibacterial/antifungal agents clavulanic acid, collismycin A, frontalamides, kanamycin, streptomycin and streptothricin; the protein phosphatase inhibitor RK-682; and the acute iron poisoning medication desferrioxamine B. The genome sequence reported here will enable us to study the biosynthetic mechanism of these important antibiotics and will facilitate the discovery of novel secondary metabolites with potential applications to human health.
2. Collismycin A biosynthesis in Streptomyces sp. CS40 is regulated by iron levels through two pathway-specific regulators
José A Salas, Carlos Olano, Carmen Méndez, Natalia M Vior, Ignacio García Microbiology (Reading) . 2014 Mar;160(Pt 3):467-478. doi: 10.1099/mic.0.075218-0.
Two putative pathway-specific regulators have been identified in the collismycin A gene cluster: ClmR1, belonging to the TetR-family, and the LuxR-family transcriptional regulator ClmR2. Inactivation of clmR1 led to a moderate increase of collismycin A yields along with an early onset of its production, suggesting an inhibitory role for the product of this gene. Inactivation of clmR2 abolished collismycin A biosynthesis, whereas overexpression of ClmR2 led to a fourfold increase in production yields, indicating that ClmR2 is an activator of collismycin A biosynthesis. Expression analyses of the collismycin gene cluster in the wild-type strain and in ΔclmR1 and ΔclmR2 mutants confirmed the role proposed for both regulatory genes, revealing that ClmR2 positively controls the expression of most of the genes in the cluster and ClmR1 negatively regulates both its own expression and that of clmR2. Additionally, production assays and further transcription analyses confirmed the existence of a higher regulatory level modulating collismycin A biosynthesis in response to iron concentrations in the culture medium. Thus, high iron levels inhibit collismycin A biosynthesis through the repression of clmR2 transcription. These results have allowed us to propose a regulatory model that integrates the effect of iron as the main environmental stimulus controlling collismycin A biosynthesis.
3. Caerulomycin and collismycin antibiotics share a trans-acting flavoprotein-dependent assembly line for 2,2'-bipyridine formation
Shengjie Guo, Zhuhua Wu, Zhijun Tang, Rijing Liao, Bo Pang, Wen Liu Nat Commun . 2021 May 25;12(1):3124. doi: 10.1038/s41467-021-23475-4.
Linear nonribosomal peptide synthetases (NRPSs) and polyketide synthases (PKSs) template the modular biosynthesis of numerous nonribosomal peptides, polyketides and their hybrids through assembly line chemistry. This chemistry can be complex and highly varied, and thus challenges our understanding in NRPS and PKS-programmed, diverse biosynthetic processes using amino acid and carboxylate building blocks. Here, we report that caerulomycin and collismycin peptide-polyketide hybrid antibiotics share an assembly line that involves unusual NRPS activity to engage a trans-acting flavoprotein in C-C bond formation and heterocyclization during 2,2'-bipyridine formation. Simultaneously, this assembly line provides dethiolated and thiolated 2,2'-bipyridine intermediates through differential treatment of the sulfhydryl group arising from L-cysteine incorporation. Subsequent L-leucine extension, which does not contribute any atoms to either caerulomycins or collismycins, plays a key role in sulfur fate determination by selectively advancing one of the two 2,2'-bipyridine intermediates down a path to the final products with or without sulfur decoration. These findings further the appreciation of assembly line chemistry and will facilitate the development of related molecules using synthetic biology approaches.
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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 ╳
