Calcimycin (hemimagnesium)

Calcimycin (A-23187) hemimagnesium is an antibiotic and a unique divalent cation ionophore (like calcium and magnesium) . Calcimycin hemimagnesium induces Ca2+-dependent cell death by increasing intracellular calcium concentration. Calcimycin hemimagnesium inhibits the growth of Gram-positive bacteria and some fungi. Calcimycin hemimagnesium also inhibits the activity of ATPase and uncouples oxidative phosphorylation (OXPHOS) of mammalian cells. Calcimycin hemimagnesium induces apoptosis and autophagy[1][2][3][4][5].

Product Specifications

CAS Number

[72124-77-7]

Product Name Alternative

A-23187 (hemimagnesium) ; Antibiotic A-23187 (hemimagnesium)

UNSPSC

12352005

Hazard Statement

H302+H312+H332-H315-H319-H335

Target

Antibiotic; Apoptosis; Autophagy; Bacterial; Fungal; Oxidative Phosphorylation

Type

Reference compound

Related Pathways

Anti-infection; Apoptosis; Autophagy; Metabolic Enzyme/Protease

Applications

Cancer-Kinase/protease

Field of Research

Cancer; Infection

Assay Protocol

https://www.medchemexpress.com/calcimycin-hemimagnesium.html

Solubility

10 mM in DMSO

Smiles

CNC1=CC=C2OC(C[C@@H]3[C@@H](CC[C@@]4(O3)[C@@H](C[C@H]([C@H](O4)[C@@H](C(C5=CC=CN5)=O)C)C)C)C)=NC2=C1C([O-][Mg+2][O-]C(C6=C7N=C(C[C@H]8O[C@]9(O[C@H]([C@H](C)C(C%10=CC=CN%10)=O)[C@H](C)C[C@H]9C)CC[C@H]8C)OC7=CC=C6NC)=O)=O

Molecular Formula

C58H72MgN6O12

Molecular Weight

1069.53

Precautions

P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

References & Citations

[1]Wu Q, et al. 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.|[2]Elliott JI, et al. IKCa1 activity is required for cell shrinkage, phosphatidylserine translocation and death in Tlymphocyte apoptosis. EMBO Rep. 2003 Feb;4 (2) :189-94.|[3]Engedal N, et al. Modulation of intracellular calcium homeostasis blocks autophagosome formation. Autophagy. 2013 Oct;9 (10) :1475-90.|[4]Mawatwal S, et al. Calcimycin mediates mycobacterial killing by inducing intracellular calcium-regulated autophagy in a P2RX7 dependent manner. Biochim Biophys Acta Gen Subj. 2017 Dec;1861 (12) :3190-3200.|[5]Wang JP, et al. Effect of norathyriol, isolated from Tripterospermum lanceolatum, on A23187-induced pleurisy and analgesia in mice. Naunyn Schmiedebergs Arch Pharmacol. 1994 Jul;350 (1) :90-5.