Calcimycin

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

Product information

CAS Number: 52665-69-7

Molecular Weight: 523.62

Formula: C29H37N3O6

Synonym:

A-23187

Antibiotic A-23187

Chemical Name: 5-(methylamino)-2-{[(2R, 3R, 6S, 8S, 9R, 11R)-3, 9, 11-trimethyl-8-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1, 7-dioxaspiro[5.5]undecan-2-yl]methyl}-1, 3-benzoxazole-4-carboxylic acid

Smiles: CNC1=CC=C2OC(C[C@H]3O[C@@]4(CC[C@H]3C)O[C@H]([C@H](C)C(=O)C3=CC=CN3)[C@H](C)C[C@H]4C)=NC2=C1C(O)=O

InChiKey: HIYAVKIYRIFSCZ-CYEMHPAKSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 50 mg/mL (95.49 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Calcimycin (A-23187) mediates mycobacterial killing by inducing intracellular calcium-regulated autophagy in a P2RX7 dependent manner.

In Vivo:

Calcimycin (A-23187) (2.5 or 7.5 nM; intrapleurally) induces protein leakage.

References:

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.

Products are for research use only. Not for human use.