C7522

Calcium Ionophore A23187

≥98% (TLC), powder

• 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

Properties

• 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

Description

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.

Safety Information

• 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