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MedKoo Cat#: 574189 | Name: Collismycin A
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Collismycin A is a bacterial metabolite with antibacterial, antiproliferative, and neuroprotective properties. It is active against a variety of bacteria and fungi. It inhibits proliferation of A549 lung, HCT116 colon, HeLa cervical cancer cells, and NIH373 fibroblasts but not MDA-MD-231 breast cancer cells. 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.

Chemical Structure

Collismycin A
CAS#158792-24-6

Theoretical Analysis

MedKoo Cat#: 574189

Name: Collismycin A

CAS#: 158792-24-6

Chemical Formula: C13H13N3O2S

Exact Mass: 275.0728

Molecular Weight: 275.33

Elemental Analysis: C, 56.71; H, 4.76; N, 15.26; O, 11.62; S, 11.64

Price and Availability

Size Price Availability Quantity
1mg USD 750.00 2 Weeks
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Related CAS #
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Synonym
Collismycin A; SF 2738A; SF2738A; SF-2738A
IUPAC/Chemical Name
(E)-4-methoxy-5-(methylthio)-[2,2'-bipyridine]-6-carbaldehyde oxime
InChi Key
NQGMIPUYCWIEAW-OVCLIPMQSA-N
InChi Code
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+
SMILES Code
COC1=C(SC)C(/C=N/O)=NC(C2=NC=CC=C2)=C1
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 275.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Vior NM, Olano C, García I, Méndez C, Salas JA. 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. doi: 10.1099/mic.0.075218-0. Epub 2013 Dec 18. PMID: 24353310. 2: Kawatani M, Muroi M, Wada A, Inoue G, Futamura Y, Aono H, Shimizu K, Shimizu T, Igarashi Y, Takahashi-Ando N, Osada H. Proteomic profiling reveals that collismycin A is an iron chelator. Sci Rep. 2016 Dec 6;6:38385. doi: 10.1038/srep38385. PMID: 27922079; PMCID: PMC5138588. 3: Pang B, Liao R, Tang Z, Guo S, Wu Z, Liu W. Caerulomycin and collismycin antibiotics share a trans-acting flavoprotein-dependent assembly line for 2,2'-bipyridine formation. Nat Commun. 2021 May 25;12(1):3124. doi: 10.1038/s41467-021-23475-4. PMID: 34035275; PMCID: PMC8149447. 4: Choi H, Lee W, Kim E, Ku SK, Bae JS. Inhibitory effects of collismycin C and pyrisulfoxin A on particulate matter-induced pulmonary injury. Phytomedicine. 2019 Sep;62:152939. doi: 10.1016/j.phymed.2019.152939. Epub 2019 Apr 23. PMID: 31100678. 5: Garcia I, Vior NM, González-Sabín J, Braña AF, Rohr J, Moris F, Méndez C, Salas JA. 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. doi: 10.1016/j.chembiol.2013.06.014. Epub 2013 Aug 1. PMID: 23911584. 6: Kim E, Ku SK, Yang S, Lee BS, Kim GJ, Choi H, Bae JS. Collismycin C reduces HMGB1-mediated septic responses and improves survival rate in septic mice. J Asian Nat Prod Res. 2021 Jan;23(1):55-72. doi: 10.1080/10286020.2019.1706497. Epub 2019 Dec 31. PMID: 31888389. 7: Garcia I, Vior NM, Braña AF, González-Sabin J, Rohr J, Moris F, Méndez C, Salas JA. Elucidating the biosynthetic pathway for the polyketide-nonribosomal peptide collismycin A: mechanism for formation of the 2,2'-bipyridyl ring. Chem Biol. 2012 Mar 23;19(3):399-413. doi: 10.1016/j.chembiol.2012.01.014. PMID: 22444595. 8: Lee BS, Kim E, Choi H, Bae JS. Suppressive functions of collismycin C in TGFBIp-mediated septic responses. J Nat Med. 2020 Mar;74(2):387-398. doi: 10.1007/s11418-019-01374-9. Epub 2019 Nov 23. PMID: 31760555. 9: Lee JH, Kim E, Choi H, Lee J. Collismycin C from the Micronesian Marine Bacterium Streptomyces sp. MC025 Inhibits Staphylococcus aureus Biofilm Formation. Mar Drugs. 2017 Dec 12;15(12):387. doi: 10.3390/md15120387. PMID: 29231844; PMCID: PMC5742847. 10: Chen Z, Ou P, Liu L, Jin X. 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. doi: 10.3389/fmicb.2020.00555. PMID: 32318039; PMCID: PMC7154055. 11: Chen D, Zhao Q, Liu W. Discovery of caerulomycin/collismycin-type 2,2'-bipyridine natural products in the genomic era. J Ind Microbiol Biotechnol. 2019 Mar;46(3-4):459-468. doi: 10.1007/s10295-018-2092-7. Epub 2018 Nov 27. PMID: 30484122. 12: Sialer C, García I, González-Sabín J, Braña AF, Méndez C, Morís F, Salas JA. Generation by mutasynthesis of potential neuroprotectant derivatives of the bipyridyl collismycin A. Bioorg Med Chem Lett. 2013 Oct 15;23(20):5707-9. doi: 10.1016/j.bmcl.2013.08.017. Epub 2013 Aug 12. PMID: 23993774. 13: Ma Y, Guo P, Chen X, Xu M, Liu W, Jin X. Anti-Klebsiella pneumoniae activity of secondary metabolism of Achromobacter from the intestine of Periplaneta americana. BMC Microbiol. 2023 Jun 5;23(1):162. doi: 10.1186/s12866-023-02909-7. PMID: 37277707; PMCID: PMC10240788. 14: Ku SK, Jeong SY, Yang S, Kim KM, Choi H, Bae JS. Suppressive effects of collismycin C on polyphosphate-mediated vascular inflammatory responses. Fitoterapia. 2019 Apr;134:447-453. doi: 10.1016/j.fitote.2019.03.022. Epub 2019 Mar 23. PMID: 30914331. 15: Liu W, Li E, Liu L, Tian F, Luo X, Cai Y, Wang J, Jin X. Antifungal activity of compounds from Gordonia sp. WA8-44 isolated from the gut of Periplaneta americana and molecular docking studies. Heliyon. 2023 Jul 4;9(7):e17777. doi: 10.1016/j.heliyon.2023.e17777. PMID: 37539250; PMCID: PMC10395128. 16: Ma X, Tang Z, Ding W, Liu T, Yang D, Liu W, Ma M. Structure-Based Mechanistic Insights into ColB1, a Flavoprotein Functioning in-trans in the 2,2'-Bipyridine Assembly Line for Cysteine Dehydrogenation. ACS Chem Biol. 2023 Jan 20;18(1):18-24. doi: 10.1021/acschembio.2c00785. Epub 2023 Jan 5. PMID: 36603145. 17: Bu YY, Yamazaki H, Ukai K, Namikoshi M. Anti-mycobacterial nucleoside antibiotics from a marine-derived Streptomyces sp. TPU1236A. Mar Drugs. 2014 Dec 17;12(12):6102-12. doi: 10.3390/md12126102. PMID: 25522318; PMCID: PMC4278220. 18: Liang L, Haltli B, Marchbank DH, Fischer M, Kirby CW, Correa H, Clark TN, Gray CA, Kerr RG. Discovery of an Isothiazolinone-Containing Antitubercular Natural Product Levesquamide. J Org Chem. 2020 May 15;85(10):6450-6462. doi: 10.1021/acs.joc.0c00339. Epub 2020 May 4. PMID: 32363877. 19: Stadler M, Bauch F, Henkel T, Mühlbauer A, Müller H, Spaltmann F, Weber K. Antifungal actinomycete metabolites discovered in a differential cell-based screening using a recombinant TOPO1 deletion mutant strain. Arch Pharm (Weinheim). 2001 May;334(5):143-7. doi: 10.1002/1521-4184(200105)334:5<143::aid- ardp143>3.0.co;2-b. PMID: 11413818. 20: Shindo K, Yamagishi Y, Okada Y, Kawai H. Collismycins A and B, novel non- steroidal inhibitors of dexamethasone-glucocorticoid receptor binding. J Antibiot (Tokyo). 1994 Sep;47(9):1072-4. doi: 10.7164/antibiotics.47.1072. PMID: 7928696.

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