ChemicalBook > CAS DataBase List > A23187

A23187

Product Name
A23187
CAS No.
52665-69-7
Chemical Name
A23187
Synonyms
SBE-β-CD;CALCIMYCIN;A23187, 98%, FREE ACID;CALCIUM IONOPHORE A23187;5-(Methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)-ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-4-benzoxazolecarboxylic acid;11B1;A23187;(R*),9B2;Calimycin;(2S*,3S*),8B2
CBNumber
CB4315720
Molecular Formula
C29H37N3O6
Formula Weight
523.62
MOL File
52665-69-7.mol
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A23187 Property

Melting point:
187-190 °C
alpha 
D25 -56° (c = 1 in chloroform)
Boiling point:
710.3±55.0 °C(Predicted)
Density 
1.28±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
Soluble in DMSO with warming or sonication. Also soluble in ethanol or ethyl acetate
form 
Solid
pka
pKa1 6.9 in 90% DMSO
color 
white to light yellow
Merck 
13,1639
BRN 
1096801
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 4 months.
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Safety

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-20/21/22
Safety Statements 
26-36
WGK Germany 
3
RTECS 
DM4676000
F 
8
HS Code 
29349990
Toxicity
LD50 i.p. in mice: 10 mg/kg (Gale)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
100105
Product name
A23187, Free Acid,
Packaging
1mg
Price
$54.7
Updated
2024/03/01
Sigma-Aldrich
Product number
100105
Product name
A23187, Free Acid,
Packaging
5mg
Price
$142
Updated
2024/03/01
Sigma-Aldrich
Product number
21186
Product name
Calcium ionophore III
Purity
Selectophore?, function tested
Packaging
5mg
Price
$112
Updated
2022/05/15
Sigma-Aldrich
Product number
21186
Product name
Calcium ionophore III
Purity
Selectophore?, function tested
Packaging
25mg
Price
$406
Updated
2022/05/15
Alfa Aesar
Product number
J63020
Product name
Antibiotic A23187, 98%
Packaging
10mg
Price
$249
Updated
2024/03/01
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A23187 Chemical Properties,Usage,Production

Description

Antibiotic A-23187 (52665-69-7) is a highly selective divalent cation ionophore, commonly used to increase intracellular Ca2+ levels in intact cells (though it is most selective for Mn2+).1 It uncouples oxidative phosphorylation.2 In addition, antibiotic A-23187 inhibits ATPase activity.3

Chemical Properties

white to off-white solid

Uses

Calcimycin is a potent calcium ionophore isolated from Streptomyces chartreusis in 1974. Calcimycin is a spiroketal substituted by pyrollic and benzoxazolyl groups which afford its high affinity and selectivity for calcium. Calimycin exhibits broad biological activity against bacteria, fungi and protozoa. It has found wide application as a research tool for calcium-regulated cellular events.

Uses

A23187 (Mixed Calcium-Magnesium Salt) is used in cell activation experiments when calcium dose-response data are not required. Ca-Mg ratio ~ 1:1. it is widely used as a compound in cell activation. It is used as a highly selective Ca2+ ionophore. it is used in studies of intracellular Ca2+ mediated events. A23187 has been observed to induce cell activation, differentiation or proliferation. In vitro experimentation has shown A23187 to boost ROS generation and platelet fragmentation. A23187 is a widely used ionophore. It has the ability to increase the intracellular concentrations of cations and is widely used to increase the intracellular levels of calcium. Visualization of Synaptic Ca2+ Calmodulin-Dependent Protein Kinase II Activity in Living Neurons.

Uses

CA was used in elucidating the mechanisms underlying the positive and inotropic and chronotropic ability of CA on isolated superfused guinea pig atria. It may also be used to stimulate and measure the erythrocyte Ca2+ dependent K+ channels as the K+ efflux.

Definition

ChEBI: 5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid is a benzoxazole.

General Description

A mobile ion-carrier that forms stable complexes with divalent cations. Useful for increasing intracellular Ca2+ levels. Also acts as an uncoupler of oxidative phosphorylation and inhibitor of mitochondrial ATPase activity. An antibiotic with weak activity against Gram-positive bacteria. Also induces apoptosis in mouse lymphoma cell line (S49); however, A23187 has been shown to block apoptosis in other systems, such as when interleukin-3 (IL-3) is withdrawn from IL-3-dependent cells.

Biological Activity

Calcium ionophore that induces Ca 2+ -dependent cell death by increasing intracellular calcium concentration. Promotes intracelllular ROS generation and platelet particle formation (fragmentation) in vitro and in vivo .

Biochem/physiol Actions

Primary TargetMitochondrial ATPase

storage

+4°C (desiccate)

Purification Methods

It recrystallises from Me2CO as colourless needles. Protect it from light and moisture, store in a refrigerator. It is soluble in Me2SO or EtOH and can be stored for 3 months without loss of activity. The Mg and Ca salts are soluble in organic solvents and cross biological membranes. It has a pKa of 6.9 in 90% Me2SO. The Ca complex crystallises from 50% EtOH as colourless prisms. It is highly TOXIC. [Pressman Ann Rev Biochem 45 501 1976, Chaney et al. J Am Chem Soc 96 1932 1974, Chaney et al. J Antibiotics 29 124 1976, Suzuki et al. Anal Biochem 61 382 1989, Simon & Carafoli Methods Enzymol 56 439 1977.]

References

1) Reed and Lardy (1972) A23187: a divalent cation ionophore; J. Biol. Chem, 247 6970 2) Wong et al. (1973) Effects of antibiotic ionophore, A23187, on oxidative phosphorylation and calcium transport of liver mitochondria; Arch. Biochem. Biophys, 156 578 3) Hara and Kanazawa (1986) Selective inhibition by ionophore A23187 of the enzyme isomerization in the catalytic cycle of sarcoplasmic reticulum Ca2+-ATPase; J. Biol. Chem., 261 16584

A23187 Preparation Products And Raw materials

Raw materials

Preparation Products

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A23187 Suppliers

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52665-69-7, A23187Related Search:

1,7-DIOXASPIRO[5.5]UNDECANE 2-ETHYL-BENZOOXAZOLE 4-ISOBUTOXY-2-BUTANONE A23187 2-PROPIONYLPYRROLE CALCIMYCIN HEMICALCIUM SALT Magnesium 4-BROMO-A23187 2-BUTYL-1,3-BENZOXAZOL-5-AMINE 1,1-DI(2-METHYLBUTOXY)ETHANE 1,1-DI-ISOBUTOXYPROPANE 2-METHYL-1,3-BENZOXAZOL-5-AMINE 5-AMINOBENZOOXAZOLE CALCIMYCIN A23187 HEMIMAGNESIUM SALT 2-ETHYL-1,3-BENZOXAZOL-5-AMINE 4-BROMO-CALCIUM IONOPHORE A23187 FREE AC A23187,freeacid Calcium ionophore A23187（free acid）

  • A23187 (CalciMycin)
  • CALCIUM IONOPHORE III
  • CALCIUM IONOPHORE A23187
  • CALCIMYCIN
  • CALCIMYCIN A23187
  • IONOPHORE A-23187
  • 5-(Methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)-ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-4-benzoxazolecarboxylic acid
  • Bis[5-methylamino-2-[[(6S)-3β,9α,11β-trimethyl-8α-[(S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2β-yl]methyl]-4-benzoxazolecarboxylic acid]calcium salt
  • 5-(Methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-4-benzoxazolecarboxylic acid
  • 5-Methylamino-2-[[(2R,3R,6S)-3,9α,11β-trimethyl-8α-[(S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-4-benzoxazolecarboxylic acid
  • Calcium ionophore A23187, 98%, from Streptomyces chartreusis
  • A 23187, CaliMycin
  • CalciuM Ionophore A23187, froM StreptoMyces chartreusis
  • Calcimycin [Calcium Ionophore A23187]
  • 4-Benzoxazolecarboxylicacid,5-(methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-
  • CALIMYCIN;ANTIBIOTIC A 23187
  • A23187, Free Acid, Streptomyces chartreusensis - CAS 52665-69-7 - Calbiochem
  • Calcimycin hydrate
  • 4-BENZOXAZOLECARBOXYLIC ACID, 5-(METHYLAMINO)-2-((3,9,11-TRIMETHYL-8-(1-METHYL-2-OXO-2-(1H-PYRROL-2-YL)ETHYL)-1,7-DIOXASPIRO(5.5)UNDEC-2-YL)METHYL)-(6S-(6ALPHA(2S*,3S*),8BETA(R),9BETA,11ALPHA))-
  • 5-(METHYLAMINO)-2-[[[2R,3R,6S,8S,9R,11R]-3,9,11-TRIMETHYL-8-[(1S)-1-METHYL-2-OXO-2-(1H-PYRROL-2-YL)-ETHYL]-1,7-DIOXASPIRO[5.5]UNDEC-2-YL]METHYL]-4-BENZOXAZOLECARBOXYLIC ACID
  • A23187
  • ANTIBIOTIC A23187
  • 2-oxo-2-(1h-pyrrol-2-yl)ethyl)-1,7-dioxaspiro(5.5)undec-2-yl)methyl),(6s-(6-a
  • 3s*),8-beta(r*),9-beta,11-alpha))-lpha(2s
  • 5-(methylamino)-2-((3,9,11-trimethyl-8-(1-methyl-4-benzoxazolecarboxylicaci
  • Calimycin
  • CALCIMYCIN A23187 FREE ACID
  • CALCIUM IONOPHORE (CALCIMYCIN) FREE ACID III
  • 4-Benzoxazolecarboxylic acid, 5-(methylamino)-2-((3,9,11-trimethyl-8-(1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl)-1,7-dioxaspiro(5.5)undec-2-yl)methyl)-, (6S-(6alpha(2S*,3S*),8beta(R*),9beta,11alpha))-, A23187 (free acid), Calcimycin, Calcium Ionophore A23187
  • Antibiotic A 23187, Calcium Ionophore A23187, Calimycin
  • Antibiotic A 23187, Calimycin
  • A23187, 98%, MIXED CALCIUM-MAGNESIUM SALT
  • A23187, 98%, FREE ACID
  • (2S*,3S*),8B2
  • (R*),9B2
  • 11B1
  • 4-Benzoxazolecarboxylic acid, 5-(methylamino)-2-[[3,9,11-trimethyl-8-[1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-, [6S-[6B1
  • SBE-β-CD
  • Calcimycin (Mixed Ca/Mg salt)
  • 52665-69-7
  • C29H36N3O6xCaxMg
  • C29H37N3O6
  • BioChemical
  • Antibiotics
  • Antibiotics A-F
  • Antibiotics A to Z
  • Signalling
  • antibiotic
  • Calcium channel