100105

A23187 free acid

from Streptomyces chartreusensis, ≥98% (TLC), solid, mitochondrial ATPase inhibitor, Calbiochem^®

• Synonym(s): A23187, Free Acid, Streptomyces chartreusensis, Calcimycin
• Empirical Formula (Hill Notation): C₂₉H₃₇N₃O₆
• CAS Number: 52665-69-7
• Molecular Weight: 523.62
• UNSPSC Code: 12352106
• NACRES: NA.77
• MDL number: MFCD00151202
• Assay: ≥98% (TLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Properties

• Product Name: A23187, Free Acid, Streptomyces chartreusensis, A mobile ion-carrier that forms stable complexes with divalent cations.
• Quality Segment: 100
• description: Merck USA index - 14, 1639
• assay: ≥98% (TLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: white
• solubility: DMSO: soluble, methanol: soluble
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: [nH]1c(ccc1)C(=O)C([C@H]2OC3(O[C@H]([C@H](CC3)C)Cc4nc5c([o]4)ccc(c5C(=O)O)NC)[C@@H](C[C@H]2C)C)C
• 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?/m0/s1
• InChI key: HIYAVKIYRIFSCZ-CVXKHCKVSA-N

Description

General description

A mobile ion-carrier that forms stable complexes with divalent cations. Useful for increasing intracellular Ca²⁺ levels. Also acts as an uncoupler of oxidative phosphorylation and inhibitor of mitochondrial ATPase activity. An antibiotic with weak activity against Gram positive bacteria. Also induces apoptosis in mouse lymphoma cell line (S49); however, A23187 has been shown to block apoptosis in other systems, such as when interleukin-3 (IL-3) is withdrawn from IL-3-dependent cells.

Biochem/physiol Actions

Cell permeable: no

Primary Target
Mitochondrial ATPase

Product does not compete with ATP.

Reversible: no

Preparation Note

For use in aqueous systems, preparation of a 100 mM stock in DMSO is recommended. Microliter amounts of this solution can then be added to H₂O with rapid mixing (e.g. 10 µl into 5 ml of H₂O). In aqueous systems, the ionophore aggregates over time.

Other Notes

Caron-Leslie, L.A., et al. 1994. FASEB J.8, 639.
Saunders, M.J., and Hepler, P.K. 1982. Science217, 943.
Pressman, B.C. 1976. Annu. Rev. Biochem. 45,501.
Pfeiffer, D.R., et al. 1974. Biochemistry 13, 4007.
Reed, P.W., and Lardy, H.A. 1972. J. Biol. Chem. 247, 6970.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable