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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:
Molecular Weight:
523.62
Beilstein/REAXYS Number:
1096801
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.32

sterility

non-sterile

Quality Level

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cell line (S49)7 but also has been shown to block apoptosis in other systems, such as when interleukin-3 (IL-3) is withdrawn from IL-3-dependent cells.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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Storage Class

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flash_point_f

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flash_point_c

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Sebastian Lourido et al.
The EMBO journal, 31(24), 4524-4534 (2012-11-15)
Calcium signalling coordinates motility, cell invasion, and egress by apicomplexan parasites, yet the key mediators that transduce these signals remain largely unknown. One underlying assumption is that invasion into and egress from the host cell depend on highly similar systems
Ian T Foe et al.
mSphere, 3(5) (2018-09-21)
Hydrolase are enzymes that regulate diverse biological processes, including posttranslational protein modifications. Recent work identified four active serine hydrolases (ASHs) in Toxoplasma gondii as candidate depalmitoylases. However, only TgPPT1 (ASH1) has been confirmed to remove palmitate from proteins. ASH4 (TgME49_264290)
Sharissa L Latham et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 27(2), 672-683 (2012-11-20)
Elevated endothelial microparticle (MP) levels are observed in numerous diseases, increasingly supporting roles as effectors and valuable markers of vascular dysfunction. While a contractile role for the actin cytoskeleton has been implicated in vesiculation, i.e., MP production, the precise interactions
Armen V Gyulkhandanyan et al.
British journal of haematology, 161(2), 245-254 (2013-02-13)
Anucleate platelets perform two fundamental processes, activation and apoptosis. We elaborated an approach for selective and concurrent stimulation of platelet apoptosis and/or activation, processes important in haemostasis and platelet clearance. Human platelets were treated with BH3 mimetic ABT-737, thrombin, calcium
Jeannine Winkler et al.
Thrombosis and haemostasis, 109(3), 532-539 (2013-01-12)
Although platelets possess the hallmarks of apoptosis such as activation of caspases, cytochrome c release and depolarisation of the mitochondrial transmembrane potential (∆Ψm), their entire apoptotic-signalling pathway is not totally understood. Therefore we studied the expression of various apoptotic proteins

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