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C7522

Sigma-Aldrich

Calcium Ionophore A23187

≥98% (TLC), powder

Synonym(s):

Calcimycin, Antibiotic A 23187, Calimycin

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About This Item

Empirical Formula (Hill Notation):
C29H37N3O6
CAS Number:
52665-69-7
Molecular Weight:
523.62
Beilstein/REAXYS Number:
1096801
EC Number:
258-084-1
MDL number:
MFCD00151202
UNSPSC Code:
12352200
PubChem Substance ID:
24277964
NACRES:
NA.32

sterility

non-sterile

Quality Level

300

assay

≥98% (TLC)

form

powder

color

white to light yellow

solubility

ethanol: 5 mg/mL
DMSO: 50 mg/mL

antibiotic activity spectrum

Gram-positive bacteria
fungi

mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

[H][C@@]1(O[C@@]2(CC[C@@H](C)[C@@H](Cc3nc4c(C(O)=O)c(NC)ccc4o3)O2)[C@H](C)C[C@H]1C)[C@H](C)C(=O)c5ccc[nH]5

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

InChI key

HIYAVKIYRIFSCZ-CYEMHPAKSA-N

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General description

Calcium ionophore A23187 is a carboxylic acid antibiotic with weak in vitro activity against Gram-positive organisms. It increases the potential of divalent ions to cross biological membranes, thus it acts as an ionophore. Calcium ionophore A23187 specifically forms stable 2:1 complex with divalent cations, rendering these ions soluble in ordinary organic solvents. Since calcium ionophore A23187 is commonly used to increase intracellular Ca2+ levels in intact cells, it acts as an uncoupler of oxidative phosphorylation and an inhibitor of mitochondrial adenosine triphosphatase (ATPase) activity. Calcium Ionophore A23187 is a potent inducer of phosphorylation of Toxoplasma eukaryotic initiation factor-2α (eIF2α). It also induces apoptosis in mouse lymphoma cell line (S49)7 but also has been shown to block apoptosis in other systems, such as when interleukin-3 (IL-3) is withdrawn from IL-3-dependent cells. Calcium ionophore A23187 is widely used as artificial activating substances for human oocytes.
with heating or sonication. Solutions are stable for at least 3 months at -20 °C when protected from light and water contamination.
with heating. Solutions are stable for at least 3 months at -20 °C when protected from light and water contamination.

Application

Calcium ionophore A23187 has been used:
  • as an endoplasmic reticulum (ER) stress inducer to study its effect on the expression of the toxoplasma unfolded protein response (UPR) genes
  • for the induction of the acrosome reaction
  • in skeletal muscle sarcoplasmic reticulum Ca2+ ATPase (SERCA) activity assay

Ionophore 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.

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Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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