A23187

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Synomyms: Calcimycin, Ionophore A23187, Antibiotic A23187, A-23187, A 23187

IUPAC Name:

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

Functional Activity:

A23187 is a mobile ion-carrier that forms stable complexes with divalent cations (ions with a charge of +2). It is highly selective for Ca²⁺. Potentiates responses to NMDA but not quisqualate. In cell culture, stimulates nitric oxide production by calmodulin-dependent constitutive nitric oxide synthase.

Technical Data:

M.Wt: 523.63

Formula: C₂₉H₃₇ N₃O₆

Solubility: Soluble to 10 mM in ethanol and to 50 mM in DMSO

Purity: >98%

Storage: Dessicate at 4°C

CAS No.: 52665-69-7

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References for A23187:

1. Leytin, V., Mutlu, A., Mykhaylov, S., Allen, D. J., Gyulkhandanyan, A. V., and Freedman, J. The GPIIbIIIa antagonist drugs eptifibatide and tirofiban do not induce activation of apoptosis executioner caspase-3 in resting platelets but inhibit caspase-3 activation in platelets stimulated with thrombin or calcium ionophore A23187. Haematologica, 94: 1783-1784, 2009.

2. Zhang, J., Ding, X., Bian, Z., Xia, Y., Lu, C., Wang, S., Song, L., and Wang, X. The effect of anti-eppin antibodies on ionophore A23187-induced calcium influx and acrosome reaction of human spermatozoa. Hum Reprod, 25: 29-36.

3. Li, Z., Zhu, J. Q., and Yang, W. X. Acrosome reaction in Octopus tankahkeei induced by calcium ionophore A23187 and a possible role of the acrosomal screw. Micron, 41: 39-46.

4. Yamazaki, M., Chiba, K., and Yoshikawa, C. Genipin suppresses A23187-induced cytotoxicity in neuro2a cells. Biol Pharm Bull, 32: 1043-1046, 2009.

5. Sakanashi, Y., Oyama, T. M., Matsuo, Y., Oyama, T. B., Nishimura, Y., Ishida, S., Imai, S., Okano, Y., and Oyama, Y. Zn(2+), derived from cell preparation, partly attenuates Ca(2+)-dependent cell death induced by A23187, calcium ionophore, in rat thymocytes. Toxicol In Vitro, 23: 338-345, 2009.

6. Kar, P., Chakraborti, T., Samanta, K., and Chakraborti, S. mu-Calpain mediated cleavage of the Na+/Ca2+ exchanger in isolated mitochondria under A23187 induced Ca2+ stimulation. Arch Biochem Biophys, 482: 66-76, 2009.

7. Borges, E., Jr., de Almeida Ferreira Braga, D. P., de Sousa Bonetti, T. C., Iaconelli, A., Jr., and Franco, J. G., Jr. Artificial oocyte activation with calcium ionophore A23187 in intracytoplasmic sperm injection cycles using surgically retrieved spermatozoa. Fertil Steril, 92: 131-136, 2009.

Certificate of Analysis/MSDS is available upon request with lot number