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MedKoo Cat#: 540054 | Name: Cerulomycin A
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Description:

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

Cerulomycin A is a toxin that inhibits growth of Entamoeba. It may prevent proliferation of cancer cells, and suppresses immune responses.

Chemical Structure

Cerulomycin A
CAS# 21802-37-9

Theoretical Analysis

MedKoo Cat#: 540054

Name: Cerulomycin A

CAS#: 21802-37-9

Chemical Formula: C12H11N3O2

Exact Mass: 229.0851

Molecular Weight: 229.23

Elemental Analysis: C, 62.87; H, 4.84; N, 18.33; O, 13.96

Price and Availability

Size Price Availability Quantity
1mg USD 550.00 2 Weeks
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Related CAS #
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Synonym
Carulomycin A; Cerulomycin; AC1NTHG8; AC1N-THG8; AC1N THG8 NSC-114341; NSC114341; NSC 114341; HE185727; HE 185727; HE-185727; Caerulomycin A
IUPAC/Chemical Name
(E)-4-methoxy-[2,2'-bipyridine]-6-carbaldehyde oxime
InChi Key
JCTRJRHLGOKMCF-RIYZIHGNSA-N
InChi Code
InChI=1S/C12H11N3O2/c1-17-10-6-9(8-14-16)15-12(7-10)11-4-2-3-5-13-11/h2-8,16H,1H3/b14-8+
SMILES Code
COC1=CC(C2=NC=CC=C2)=NC(/C=N/O)=C1
Appearance
Solid powder
Purity
>98% (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
>2 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 229.23 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: Tong L, Sun W, Wu S, Han Y. Characterization of Caerulomycin A as a dual- targeting anticancer agent. Eur J Pharmacol. 2022 May 5;922:174914. doi: 10.1016/j.ejphar.2022.174914. Epub 2022 Mar 23. PMID: 35337812; PMCID: PMC9077901. 2: Zhang H, Lan M, Cui G, Zhu W. The Influence of Caerulomycin A on the Intestinal Microbiota in SD Rats. Mar Drugs. 2020 May 22;18(5):277. doi: 10.3390/md18050277. PMID: 32456087; PMCID: PMC7281470. 3: Kujur W, Gurram RK, Haleem N, Maurya SK, Agrewala JN. Caerulomycin A inhibits Th2 cell activity: a possible role in the management of asthma. Sci Rep. 2015 Oct 20;5:15396. doi: 10.1038/srep15396. PMID: 26481184; PMCID: PMC4612543. 4: Xie Y, Chen J, Wang B, Chen T, Chen J, Zhang Y, Liu X, Chen Q. Activation and enhancement of caerulomycin A biosynthesis in marine-derived Actinoalloteichus sp. AHMU CJ021 by combinatorial genome mining strategies. Microb Cell Fact. 2020 Aug 6;19(1):159. doi: 10.1186/s12934-020-01418-w. Erratum in: Microb Cell Fact. 2020 Sep 7;19(1):177. PMID: 32762690; PMCID: PMC7412835. 5: Zhu Y, Zhang Q, Li S, Lin Q, Fu P, Zhang G, Zhang H, Shi R, Zhu W, Zhang C. Insights into caerulomycin A biosynthesis: a two-component monooxygenase CrmH- catalyzed oxime formation. J Am Chem Soc. 2013 Dec 18;135(50):18750-3. doi: 10.1021/ja410513g. Epub 2013 Dec 5. PMID: 24295370. 6: Singla AK, Gurram RK, Chauhan A, Khatri N, Vohra RM, Jolly RS, Agrewala JN. Caerulomycin A suppresses immunity by inhibiting T cell activity. PLoS One. 2014 Oct 6;9(10):e107051. doi: 10.1371/journal.pone.0107051. PMID: 25286329; PMCID: PMC4186789. 7: Zhu Y, Fu P, Lin Q, Zhang G, Zhang H, Li S, Ju J, Zhu W, Zhang C. Identification of caerulomycin A gene cluster implicates a tailoring amidohydrolase. Org Lett. 2012 Jun 1;14(11):2666-9. doi: 10.1021/ol300589r. Epub 2012 May 16. PMID: 22591508. 8: Kujur W, Gurram RK, Maurya SK, Nadeem S, Chodisetti SB, Khan N, Agrewala JN. Caerulomycin A suppresses the differentiation of naïve T cells and alleviates the symptoms of experimental autoimmune encephalomyelitis. Autoimmunity. 2017 Aug;50(5):317-328. doi: 10.1080/08916934.2017.1332185. Epub 2017 Jul 7. PMID: 28686480. 9: Kaur S, Srivastava G, Sharma AN, Jolly RS. Novel immunosuppressive agent caerulomycin A exerts its effect by depleting cellular iron content. Br J Pharmacol. 2015 May;172(9):2286-99. doi: 10.1111/bph.13051. Epub 2015 Feb 10. PMID: 25537422; PMCID: PMC4403094. 10: Gurram RK, Kujur W, Maurya SK, Agrewala JN. Caerulomycin A enhances transforming growth factor-β (TGF-β)-Smad3 protein signaling by suppressing interferon-γ (IFN-γ)-signal transducer and activator of transcription 1 (STAT1) protein signaling to expand regulatory T cells (Tregs). J Biol Chem. 2014 Jun 20;289(25):17515-28. doi: 10.1074/jbc.M113.545871. Epub 2014 May 8. PMID: 24811173; PMCID: PMC4067188. 11: Xie Y, Chen J, Wang B, Chen T, Chen J, Zhang Y, Liu X, Chen Q. Correction to: Activation and enhancement of caerulomycin A biosynthesis in marine-derived Actinoalloteichus sp. AHMU CJ021 by combinatorial genome mining strategies. Microb Cell Fact. 2020 Sep 7;19(1):177. doi: 10.1186/s12934-020-01429-7. Erratum for: Microb Cell Fact. 2020 Aug 6;19(1):159. PMID: 32894136; PMCID: PMC7487562. 12: FUNK A, DIVEKAR PV. Caerulomycin, a new antibiotic from Streptomyces caeruleus Baldacci. I. Production, isolation, assay, and biological properties. Can J Microbiol. 1959 Aug;5:317-21. doi: 10.1139/m59-039. PMID: 13825679. 13: Zhu Y, Picard MÈ, Zhang Q, Barma J, Després XM, Mei X, Zhang L, Duvignaud JB, Couture M, Zhu W, Shi R, Zhang C. Flavoenzyme CrmK-mediated substrate recycling in caerulomycin biosynthesis. Chem Sci. 2016 Aug 1;7(8):4867-4874. doi: 10.1039/c6sc00771f. Epub 2016 Apr 13. PMID: 30155134; PMCID: PMC6016722. 14: Lahoum A, Sabaou N, Bijani C, Bouras N, Pont F, Snini SP, Mathieu F. Antimicrobial activities of novel bipyridine compounds produced by a new strain of Saccharothrix isolated from Saharan soil. Saudi Pharm J. 2019 Jan;27(1):56-65. doi: 10.1016/j.jsps.2018.07.019. Epub 2018 Jul 20. PMID: 30662307; PMCID: PMC6323153. 15: Zhu Y, Xu J, Mei X, Feng Z, Zhang L, Zhang Q, Zhang G, Zhu W, Liu J, Zhang C. Biochemical and Structural Insights into the Aminotransferase CrmG in Caerulomycin Biosynthesis. ACS Chem Biol. 2016 Apr 15;11(4):943-52. doi: 10.1021/acschembio.5b00984. Epub 2016 Jan 12. PMID: 26714051. 16: Linardi D, She W, Zhang Q, Yu Y, Qian PY, Lam H. Proteomining-Based Elucidation of Natural Product Biosynthetic Pathways in Streptomyces. Front Microbiol. 2022 Jul 11;13:913756. doi: 10.3389/fmicb.2022.913756. PMID: 35898901; PMCID: PMC9309509. 17: Horan AM, Duong VK, McGarrigle EM. Synthesis of Bis-heteroaryls Using Grignard Reagents and Pyridylsulfonium Salts. Org Lett. 2021 Dec 3;23(23):9089-9093. doi: 10.1021/acs.orglett.1c03379. Epub 2021 Nov 16. PMID: 34784224; PMCID: PMC8650099. 18: Babadi ZK, Sudarman E, Ebrahimipour GH, Primahana G, Stadler M, Wink J. Structurally diverse metabolites from the rare actinobacterium Saccharothrix xinjiangensis. J Antibiot (Tokyo). 2020 Jan;73(1):48-55. doi: 10.1038/s41429-019-0223-7. Epub 2019 Aug 26. PMID: 31451754. 19: Chen R, Su K, Zhang Y, Zhu Y, Liu J, Xu J. Co-crystal structure provides insights on transaminase CrmG recognition amino donor L-Arg. Biochem Biophys Res Commun. 2023 Jul 9;675:41-45. doi: 10.1016/j.bbrc.2023.07.009. Epub ahead of print. PMID: 37451216. 20: Dash J, Reissig HU. A new and flexible synthesis of 4-hydroxypyridines: rapid access to caerulomycins A, E and functionalized terpyridines. Chemistry. 2009 Jul 13;15(28):6811-4. doi: 10.1002/chem.200900939. PMID: 19533694.