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A23187

A23187 Structure
A23187 structure
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
Molecular Weight:
523.62
MDL Number:
MFCD00151202
MOL File:
52665-69-7.mol
Last updated:2024-11-15 21:27:52
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A23187 Properties

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.
FDA UNII 37H9VM9WZL

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P280a-P304+P340-P305+P351+P338-P405-P501a
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)
NFPA 704
0
2 0

A23187 price More Price(29)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 100105 A23187, Free Acid, 52665-69-7 1mg $54.7 2024-03-01 Buy
Sigma-Aldrich 100105 A23187, Free Acid, 52665-69-7 5mg $142 2024-03-01 Buy
Sigma-Aldrich 21186 Calcium ionophore III Selectophore?, function tested 52665-69-7 5mg $112 2022-05-15 Buy
Sigma-Aldrich 21186 Calcium ionophore III Selectophore?, function tested 52665-69-7 25mg $406 2022-05-15 Buy
Alfa Aesar J63020 Antibiotic A23187, 98% 52665-69-7 10mg $249 2024-03-01 Buy
Product number Packaging Price Buy
100105 1mg $54.7 Buy
100105 5mg $142 Buy
21186 5mg $112 Buy
21186 25mg $406 Buy
J63020 10mg $249 Buy

A23187 Chemical Properties,Uses,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

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.

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

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.

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 synthesis

95015-27-3
52665-69-7
Synthesis of A23187 from 4-Benzoxazolecarboxylic acid, 5-[methyl(trifluoroacetyl)amino]-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]-, methyl ester, [6S-[6α(2S*,3S*),8β(R*),9β,11α]]- (9CI)

A23187 Preparation Products And Raw materials

Raw materials

4-Benzoxazolecarboxylic acid, 5-[methyl(trifluoroacetyl)amino]-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]-, methyl ester, [6S-[6α(2S*,3S*),8β(R*),9β,11α]]- (9CI)

Preparation Products

A23187 Suppliers

Global( 158)Suppliers
Supplier Tel Email Country ProdList Advantage
TargetMol Chemicals Inc. 		+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 32161 58
Alfa Chemistry 		info@alfa-chemistry.com United States 2344 58
BOC Sciences 		16314854226; +16314854226 inquiry@bocsci.com United States 19741 58
TargetMol Chemicals Inc. 		support@targetmol.com United States 38631 58
Shanghai Acmec Biochemical Technology Co., Ltd. 		+undefined18621343501 product@acmec-e.com China 33338 58
Aladdin Scientific 		+1-+1(833)-552-7181 sales@aladdinsci.com United States 57505 58
SHANGHAI KEAN TECHNOLOGY CO., LTD. 		+8613817748580 cooperation@kean-chem.com China 40066 58
Amadis Chemical Company Limited 		571-89925085 sales@amadischem.com China 131957 58
Shanghai Sinch Parmaceuticals Tech. Co. Ltd. +86-21-54098501 sales@sinch.com.cn China 11598 64
J & K SCIENTIFIC LTD. 010-82848833 400-666-7788 jkinfo@jkchemical.com China 96815 76
Supplier Advantage
TargetMol Chemicals Inc. 		58
Alfa Chemistry 		58
BOC Sciences 		58
TargetMol Chemicals Inc. 		58
Shanghai Acmec Biochemical Technology Co., Ltd. 		58
Aladdin Scientific 		58
SHANGHAI KEAN TECHNOLOGY CO., LTD. 		58
Amadis Chemical Company Limited 		58
Shanghai Sinch Parmaceuticals Tech. Co. Ltd. 64
J & K SCIENTIFIC LTD. 76

View Lastest Price from A23187 manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Calcimycin pictures 2024-11-15 Calcimycin
52665-69-7
 US $62.00 / mg 98% 10g TargetMol Chemicals Inc.
Calcimycin pictures 2024-11-15 Calcimycin
52665-69-7
 US $62.00 / mg 98% 10g TargetMol Chemicals Inc.
  • Calcimycin pictures
  • Calcimycin
    52665-69-7
  • US $62.00 / mg
  • 98%
  • TargetMol Chemicals Inc.
  • Calcimycin pictures
  • Calcimycin
    52665-69-7
  • US $62.00 / mg
  • 98%
  • TargetMol Chemicals Inc.

52665-69-7(A23187)Related 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）

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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]- 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 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 A23187 (CalciMycin) CALCIUM IONOPHORE III CALCIMYCIN A23187 IONOPHORE A-23187 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 Antibiotic A 23187, Calimycin A23187, 98%, MIXED CALCIUM-MAGNESIUM SALT Calcium ionophore A23187, 98%, from Streptomyces chartreusis CALIMYCIN;ANTIBIOTIC A 23187 A23187, Free Acid, Streptomyces chartreusensis - CAS 52665-69-7 - Calbiochem Calcimycin hydrate (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 CALCIUM IONOPHORE A23187 CALCIMYCIN 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, 98%, FREE ACID SBE-β-CD Calimycin Calcimycin (Mixed Ca/Mg salt) 52665-69-7 C29H36N3O6xCaxMg C29H37N3O6 BioChemical Antibiotics Antibiotics A-F Antibiotics A to Z Signalling antibiotic Calcium channel