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C7522

Calcium Ionophore A23187

Name: Calcium Ionophore A23187
Brand: SIGMA

≥98% (TLC), powder

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Synonym(s):

Antibiotic A 23187, Calimycin

Empirical Formula (Hill Notation):

C₂₉H₃₇N₃O₆

CAS Number:

52665-69-7

Molecular Weight:

523.62

Beilstein:

1096801

EC Number:

258-084-1

MDL number:

MFCD00151202

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 (with heating. Solutions are stable for at least 3 months at -20 °C when protected from light and water contamination.)
DMSO: 50 mg/mL (with heating or sonication. Solutions are stable for at least 3 months at -20 °C when protected from light and water contamination.)

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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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.

Biochem/physiol Actions

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 complexes 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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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