A23187

A23187

Identifiers
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
CAS Number	52665-69-7 Y
PubChem CID	11957499
ChemSpider	10131749 Y
ChEMBL	CHEMBL1256686 N
ECHA InfoCard	100.052.786
Chemical and physical data
Formula	C29H37N3O6
Molar mass	523.62 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)c1c(NC)ccc2oc(nc12)C[C@H]5O[C@]3(O[C@@H]([C@H](C)C[C@H]3C)[C@@H](C(=O)c4cccn4)C)CC[C@H]5C
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 Y Key:HIYAVKIYRIFSCZ-CYEMHPAKSA-N Y
NY (what is this?)

A23187 is a mobile ion-carrier that forms stable complexes with divalent cations (ions with a charge of +2). A23187 is also known as Calcimycin, Calcium Ionophore, Antibiotic A23187 and Calcium Ionophore A23187. It is produced at fermentation of Streptomyces chartreusensis.

A23187 has antibiotic properties against gram positive bacteria and fungi. It also acts as a divalent cation ionophore, allowing these ions to cross cell membranes, which are usually impermeable to them. A23187 is most selective for Mn²⁺, somewhat less selective for Ca²⁺ and Mg²⁺, much less selective for Sr²⁺, and even less selective for Ba²⁺. The ionophore is used in laboratories to increase intracellular Ca²⁺ levels in intact cells. It also uncouples oxidative phosphorylation, the process cells use to synthesize Adenosine triphosphate which they use for energy. In addition, A23187 inhibits mitochondrial ATPase activity. A23187 also induces apoptosis in some cells (e.g. mouse lymphoma cell line, or S49, and Jurkat cells) and prevents it in others (e.g. cells dependent on interleukin 3 that have had the factor withdrawn).

Inex Pharmaceuticals Corporation (Canada) reported an innovative application of A23187. Inex used A23187 as a molecular tool in order to make artificial liposomes loaded with anti-cancer drugs such as Topotecan.