Calcimycin

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

MedKoo CAT#: 571087

CAS#: 52665-69-7

Description: Calcimycin is an ionophorous, polyether carboxylic antibiotic from Streptomyces chartreusensis. It binds and transports calcium and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems. Calcimycin was identified as a transcriptional inhibitor of a target gene in colon cancer pathways. In addition, it is used in human fertility treatments.


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Calcimycin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 571087
Name: Calcimycin
CAS#: 52665-69-7
Chemical Formula: C29H37N3O6
Exact Mass: 523.2682
Molecular Weight: 523.63
Elemental Analysis: C, 66.52; H, 7.12; N, 8.02; O, 18.33


Synonym: Calcimycin; A23187; A 23187; A-23187; Ionophore A23187; Antibiotic 23187

IUPAC/Chemical Name: 4-Benzoxazolecarboxylic acid, 5-(methylamino)-2-((3,9,11-trimethyl-8-(1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl)-1,7-dioxaspiro(5.5)undec-2-yl)methyl)-, (6S-(6alpha(2S*,3S*),8beta(R*),9beta,11alpha))-

InChi Key: HIYAVKIYRIFSCZ-BNJSRTAHSA-N

InChi Code: InChI=1S/C29H37N3O6/c1-15-10-11-29(17(3)13-16(2)27(38-29)18(4)26(33)20-7-6-12-31-20)37-22(15)14-23-32-25-21(36-23)9-8-19(30-5)24(25)28(34)35/h6-9,12,15-18,22,27,30-31H,10-11,13-14H2,1-5H3,(H,34,35)/t15-,16+,17+,18+,22-,27-,29+/m1/s1

SMILES Code: O=C(C1=C2N=C(C[C@H]3O[C@]4(O[C@@H]([C@@H](C)C(C5=CC=CN5)=O)[C@@H](C)C[C@@H]4C)CC[C@H]3C)OC2=CC=C1NC)O


Technical Data

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).

Harmonized System Code:
293490


References

1: Wu Q, Gou L, Lin S, Liang J, Yin J, Zhou X, Bai L, An D, Deng Z, Wang Z. Characterization of the N-methyltransferase CalM involved in calcimycin biosynthesis by Streptomyces chartreusis NRRL 3882. Biochimie. 2013 Jul;95(7):1487-93. doi: 10.1016/j.biochi.2013.03.014. Epub 2013 Apr 11. PubMed PMID: 23583975.

2: Gou L, Wu Q, Lin S, Li X, Liang J, Zhou X, An D, Deng Z, Wang Z. Mutasynthesis of pyrrole spiroketal compound using calcimycin 3-hydroxy anthranilic acid biosynthetic mutant. Appl Microbiol Biotechnol. 2013 Sep;97(18):8183-91. doi: 10.1007/s00253-013-4882-1. Epub 2013 May 12. PubMed PMID: 23666477.

3: Sack U, Walther W, Scudiero D, Selby M, Aumann J, Lemos C, Fichtner I, Schlag PM, Shoemaker RH, Stein U. S100A4-induced cell motility and metastasis is restricted by the Wnt/β-catenin pathway inhibitor calcimycin in colon cancer cells. Mol Biol Cell. 2011 Sep;22(18):3344-54. doi: 10.1091/mbc.E10-09-0739. Epub 2011 Jul 27. PubMed PMID: 21795396; PubMed Central PMCID: PMC3172260.

4: Pohl P, Antonenko YN, Yaguzhinsky LS. Kinetic properties of cation/H(+)-exchange: calcimycin (A23187)-mediated Ca2+/2H(+)-exchange on the bilayer lipid membrane. Biochim Biophys Acta. 1990 Sep 7;1027(3):295-300. PubMed PMID: 2118807.

5: Li WC, Kuszak JR, Wang GM, Wu ZQ, Spector A. Calcimycin-induced lens epithelial cell apoptosis contributes to cataract formation. Exp Eye Res. 1995 Jul;61(1):91-8. PubMed PMID: 7556474.

6: Wu Q, Liang J, Lin S, Zhou X, Bai L, Deng Z, Wang Z. Characterization of the biosynthesis gene cluster for the pyrrole polyether antibiotic calcimycin (A23187) in Streptomyces chartreusis NRRL 3882. Antimicrob Agents Chemother. 2011 Mar;55(3):974-82. doi: 10.1128/AAC.01130-10. Epub 2010 Dec 20. PubMed PMID: 21173184; PubMed Central PMCID: PMC3067094.

7: Zeng GQ, Rui YC. [Inhibitory effect of dauricine on platelet activating factor released from calcimycin-induced mouse peritoneal macrophages]. Zhongguo Yao Li Xue Bao. 1990 Jul;11(4):346-50. Chinese. PubMed PMID: 2104489.

8: Santella L, Dale B. Assisted yes, but where do we draw the line? Reprod Biomed Online. 2015 Oct;31(4):476-8. doi: 10.1016/j.rbmo.2015.06.013. Epub 2015 Jul 3. PubMed PMID: 26277587.

9: Nguyen DB, Ly TB, Wesseling MC, Hittinger M, Torge A, Devitt A, Perrie Y, Bernhardt I. Characterization of Microvesicles Released from Human Red Blood Cells. Cell Physiol Biochem. 2016;38(3):1085-99. doi: 10.1159/000443059. Epub 2016 Mar 4. PubMed PMID: 26938586.

10: Li SG, Chen HJ, Yang YY, Wu WJ, Wu Y. A Novel Allyl Transfer Coupled with a Grob Fragmentation. Chem Asian J. 2015 Nov;10(11):2333-6. doi: 10.1002/asia.201500728. Epub 2015 Aug 28. PubMed PMID: 26317577.

11: Turner CT, Fuller M, Hopwood JJ, Meikle PJ, Brooks DA. Drug induced exocytosis of glycogen in Pompe disease. Biochem Biophys Res Commun. 2016 Oct 28;479(4):721-727. doi: 10.1016/j.bbrc.2016.09.145. Epub 2016 Sep 28. PubMed PMID: 27693584.

12: Prudhomme M, Guyot J, Jeminet G. Semi-synthesis of A23187 (calcimycin) analogs. IV. Cation carrier properties in mitochondria of analogs with modified benzoxazole rings. Antimicrobial activity. J Antibiot (Tokyo). 1986 Jul;39(7):934-7. PubMed PMID: 3093432.

13: Tang Y, Abe N, Yoshimoto M, Zhu B, Murata Y, Nakamura Y. Benzyl isothiocyanate inhibits IL-13 expression in human basophilic KU812 cells. Biosci Biotechnol Biochem. 2015;79(1):159-63. doi: 10.1080/09168451.2014.963503. Epub 2014 Sep 25. PubMed PMID: 25253661.

14: Nim S, Lobato LG, Moreno A, Chaptal V, Rawal MK, Falson P, Prasad R. Atomic modelling and systematic mutagenesis identify residues in multiple drug binding sites that are essential for drug resistance in the major Candida transporter Cdr1. Biochim Biophys Acta. 2016 Nov;1858(11):2858-2870. doi: 10.1016/j.bbamem.2016.08.011. Epub 2016 Aug 25. PubMed PMID: 27569110.

15: Meiniel R, Didier R, Meiniel A, Jeminet G, Prudhomme M. A radioautographic study of [3H]-A 23187 (calcimycin) in components of the brain. Distribution in different cell types of the diencephalo-mesencephalic roof. Biol Cell. 1992;74(2):239-41. PubMed PMID: 1596644.

16: Murtha AP, Feng L, Yonish B, Leppert PC, Schomberg DW. Progesterone protects fetal chorion and maternal decidua cells from calcium-induced death. Am J Obstet Gynecol. 2007 Mar;196(3):257.e1-5. PubMed PMID: 17346545.

17: Prudhomme M, Dauphin G, Jeminet G. Semi-synthesis of A23187 (calcimycin) analogs. III. Modification of benzoxazole ring substituents, ionophorous properties in an organic phase. J Antibiot (Tokyo). 1986 Jul;39(7):922-33. PubMed PMID: 3093431.

18: Prudhomme M, Dauphin G, Guyot J, Jeminet G. Semisynthesis of A23187 (calcimycin) analogs. II. Introduction of a methyl group on the benzoxazole ring. J Antibiot (Tokyo). 1984 Jun;37(6):627-34. PubMed PMID: 6430853.

19: Li SG, Wu Y. Synthesis and absolute configuration of demethyl (C-11) cezomycin. Chem Asian J. 2013 Nov;8(11):2792-800. doi: 10.1002/asia.201300623. Epub 2013 Jul 23. PubMed PMID: 23881716.

20: Geissler FT, Li DW, James ER. Inhibition of lens epithelial cell growth by induction of apoptosis: potential for prevention of posterior capsule opacification. J Ocul Pharmacol Ther. 2001 Dec;17(6):587-96. PubMed PMID: 11777182.