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C7522

Sigma-Aldrich

Calcium Ionophore A23187

≥98% (TLC), powder

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cell line (S49)7 but also has been shown to block apoptosis in other systems, such as when interleukin-3 (IL-3) is withdrawn from IL-3-dependent cells.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

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.

also commonly purchased with this product

Product No.
Description
Pricing

840857P

16:0-18:1 PA, powder

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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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Hans Wohlmuth et al.
Journal of natural products, 73(4), 743-746 (2010-03-20)
Bioactivity-guided fractionation of an ethanolic extract of the rhizome of Pleuranthodium racemigerum, a tropical Zingiberaceae species from Northeastern Australia, resulted in the isolation and structural elucidation of 1-(4''-methoxyphenyl)-7-(4'-hydroxyphenyl)-(E)-hept-2-ene (1), a new diarylheptanoid related to curcumin. Compound 1 was a fairly
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
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
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)
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