Collismycin A
(Synonyms: 碰撞霉素A) 目录号 : GC43299
A bacterial metabolite with diverse biological activities
Cas No.:158792-24-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Collismycin A is a bacterial metabolite originally isolated from Streptomyces that has diverse biological activities, including antibacterial, antiproliferative, and neuroprotective properties. It is active against a variety of bacteria (MICs = 6.25 and 100 µg/ml) and fungi (MICs = 12.5-100 µg/ml). It inhibits proliferation of A549 lung, HCT116 colon, and HeLa cervical cancer cells (IC50s = 0.3, 0.6, and 0.3 µM, respectively) and NIH373 fibroblasts (IC50 = 56.6 µM) but not MDA-MD-231 breast cancer cells (IC50 = >100 µM). Collismycin A forms a complex with Fe(II) and Fe(III) at a 2:1 ratio, and the addition of iron ions inhibits the antiproliferative effect of collismycin A on HeLa cells, an effect that does not occur with the addition of zinc, manganese, copper, or magnesium ions. Collismycin A (1 µM) prevents apoptosis in the brain region of zebrafish larvae by 44% in a model of neuronal cell death induced by all-trans retinoic acid .
| Cas No. | 158792-24-6 | SDF | |
| 别名 | 碰撞霉素A | ||
| Canonical SMILES | COC1=C(SC)C(/C=N/O)=NC(C2=NC=CC=C2)=C1 | ||
| 分子式 | C13H13N3O2S | 分子量 | 275.3 |
| 溶解度 | DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.6324 mL | 18.162 mL | 36.324 mL |
| 5 mM | 0.7265 mL | 3.6324 mL | 7.2648 mL |
| 10 mM | 0.3632 mL | 1.8162 mL | 3.6324 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Proteomic profiling reveals that Collismycin A is an iron chelator
Sci Rep 2016 Dec 6;6:38385.PMID:27922079DOI:10.1038/srep38385.
Collismycin A (CMA), a microbial product, has anti-proliferative activity against cancer cells, but the mechanism of its action remains unknown. Here, we report the identification of the molecular target of CMA by ChemProteoBase, a proteome-based approach for drug target identification. ChemProteoBase profiling showed that CMA is closely clustered with di-2-pyridylketone 4,4-dimethyl-3-thiosemicarbazone, an iron chelator. CMA bound to both Fe(II) and Fe(III) ions and formed a 2:1 chelator-iron complex with a redox-inactive center. CMA-induced cell growth inhibition was completely canceled by Fe(II) and Fe(III) ions, but not by other metal ions such as Zn(II) or Cu(II). Proteomic and transcriptomic analyses showed that CMA affects the glycolytic pathway due to the accumulation of HIF-1α. These results suggest that CMA acts as a specific iron chelator, leading to the inhibition of cancer cell growth.
Collismycin A biosynthesis in Streptomyces sp. CS40 is regulated by iron levels through two pathway-specific regulators
Microbiology (Reading) 2014 Mar;160(Pt 3):467-478.PMID:24353310DOI: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.
Engineering the biosynthesis of the polyketide-nonribosomal peptide Collismycin A for generation of analogs with neuroprotective activity
Chem Biol 2013 Aug 22;20(8):1022-32.PMID:23911584DOI:10.1016/j.chembiol.2013.06.014.
Collismycin A is a member of the 2,2'-bipyridyl family of natural products that shows cytotoxic activity. Structurally, it belongs to the hybrid polyketides-nonribosomal peptides. After the isolation and characterization of the Collismycin A gene cluster, we have used the combination of two different approaches (insertional inactivation and biocatalysis) to increase structural diversity in this natural product class. Twelve collismycin analogs were generated with modifications in the second pyridine ring of Collismycin A, thus potentially maintaining biologic activity. None of these analogs showed better cytotoxic activity than the parental collismycin. However, some analogs showed neuroprotective activity and one of them (collismycin H) showed better values for neuroprotection against oxidative stress in a zebrafish model than those of Collismycin A. Interestingly, this analog also showed very poor cytotoxic activity, a feature very desirable for a neuroprotectant compound.
Generation by mutasynthesis of potential neuroprotectant derivatives of the bipyridyl Collismycin A
Bioorg Med Chem Lett 2013 Oct 15;23(20):5707-9.PMID:23993774DOI:10.1016/j.bmcl.2013.08.017.
Collismycin A is a member of the 2,2'-bipyridyl family of natural products and structurally belongs to the hybrid polyketides-nonribosomal peptides. A gene coding for a lysine 2-aminotransferase of Streptomyces sp. CS40 (Collismycin A producer) was inactivated by gene replacement. The mutant was unable of synthesizing Collismycin A but it recovered this capability when picolinic acid was added to the culture medium. By feeding different picolinic acid analogs to this mutant, two new Collismycin A derivatives were obtained with a methyl group at the 4 and 6 position of the first pyridine ring of Collismycin A, respectively. The two compounds showed effective neuroprotective action against an oxidative stress inducer in a zebra fish model, one of them showing higher neuroprotectant activity than that of Collismycin A and that of the control lipoic acid.
Anti-MRSA Activity of Actinomycin X2 and Collismycin A Produced by Streptomyces globisporus WA5-2-37 From the Intestinal Tract of American Cockroach ( Periplaneta americana)
Front Microbiol 2020 Apr 7;11:555.PMID:32318039DOI:10.3389/fmicb.2020.00555.
Methicillin-resistant Staphylococcus aureus (MRSA) is recognized as one of the serious pathogen that causes acquired infections worldwide. Its emerging need to discover novel, safe and potent anti-MRSA drugs. In this study, primary screening by anti-MRSA activity assay found one strain WA5-2-37 isolated from the intestinal tract of Periplaneta americana, exhibited great activity against MRSA ATCC 43300. The strain WA5-2-37 produced actinomycin X2 and Collismycin A which showed strong inhibition of MRSA with minimum inhibitory concentration (MIC) values of 0.25 and 8 μg/mL. The structures of the pure compounds were elucidated by analysis of mass spectrometry (MS), 1H and 13C nuclear magnetic resonance (NMR). The strain WA5-2-37 was considered as Streptomyces globisporus on the basis of morphological characteristics, genotypic data, and phylogenetic analysis. This is the first reported naturally occurring strain of S. globisporus isolated from the intestinal tract of P. americana, whereas it has almost been found from plants, marine, and soil previously. Moreover, S. globisporus has not been reported to produce any anti-MRSA substances previously, such as actinomycin X2 and Collismycin A. In conclusion, the insect-derived strain of S. globisporus WA5-2-37 was considered of great potential as a new strain of producing actinomycin X2, Collismycin A or other anti-MRSA compounds.