72124-77-7
Chemical Structure
Calcimycin hemimagnesium
Synonym(s): A-23187 hemimagnesium; Antibiotic A-23187 hemimagnesium
- CAS No.: 72124-77-7
- Formula:C58H72MgN6O12
- Molecular Weight:1069.53
IUPAC Name: magnesium 5-(methylamino)-2-(((2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-((S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methyl)benzo[d]oxazole-4-carboxylate
InChIKey: XBWKBTZDBYFEMH-UIOMRPQBSA-L
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
Biological Activity: 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].
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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. | |||||||||||||||||||||
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- [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. [Content Brief]
- [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. [Content Brief]
- [3]. Engedal N, et al. Modulation of intracellular calcium homeostasis blocks autophagosome formation. Autophagy. 2013 Oct;9(10):1475-90. [Content Brief]
- [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. [Content Brief]
- [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. [Content Brief]
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