52665-69-7 Usage
Description
A23187, also known as Calcimycin, is a potent calcium ionophore derived from Streptomyces chartreusis. It is a spiroketal substituted by pyrollic and benzoxazolyl groups, which provide high affinity and selectivity for calcium. A23187 is a mobile ion-carrier that forms stable complexes with divalent cations and is useful for increasing intracellular Ca2+ levels. It also acts as an uncoupler of oxidative phosphorylation and an inhibitor of mitochondrial ATPase activity. A23187 is an antibiotic with weak activity against Gram-positive bacteria and has been shown to induce apoptosis in certain cell lines.
Uses
Used in Cell Activation Experiments:
A23187 is used as a compound in cell activation experiments when calcium dose-response data are not required. It is a highly selective Ca2+ ionophore with a Ca-Mg ratio of approximately 1:1.
Used in Studies of Intracellular Ca2+ Mediated Events:
A23187 is employed in research to study intracellular Ca2+ mediated events, as it has the ability to increase the intracellular concentrations of cations, particularly calcium.
Used in In Vitro Experimentation:
A23187 has been observed to induce cell activation, differentiation, or proliferation in in vitro experimentation. It has also been shown to boost reactive oxygen species (ROS) generation and platelet fragmentation.
Used in Visualization of Synaptic Ca2+ Calmodulin-Dependent Protein Kinase II Activity:
A23187 is utilized in living neurons to visualize the activity of Synaptic Ca2+ Calmodulin-Dependent Protein Kinase II.
Used in Elucidating Mechanisms of Positive Inotropic and Chronotropic Ability:
A23187 is used to study the mechanisms underlying the positive inotropic and chronotropic effects on isolated superfused guinea pig atria.
Used in Stimulating and Measuring Erythrocyte Ca2+ Dependent K+ Channels:
A23187 may be used to stimulate and measure the erythrocyte Ca2+ dependent K+ channels as the K+ efflux.
Used in Inducing Apoptosis:
A23187 has been shown to induce apoptosis in mouse lymphoma cell line (S49), although it has also been shown to block apoptosis in other systems, such as when interleukin-3 (IL-3) is withdrawn from IL-3-dependent cells.
Used in Drug Delivery Systems:
In the pharmaceutical industry, A23187 can be used to enhance the delivery, bioavailability, and therapeutic outcomes of certain drugs by employing various organic and metallic nanoparticles as carriers.
Chemical Properties:
A23187 is a white to off-white solid.
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
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
Check Digit Verification of cas no
The CAS Registry Mumber 52665-69-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,6,6 and 5 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 52665-69:
(7*5)+(6*2)+(5*6)+(4*6)+(3*5)+(2*6)+(1*9)=137
137 % 10 = 7
So 52665-69-7 is a valid CAS Registry Number.
52665-69-7Relevant articles and documents
Stereocontrolled Total Synthesis of Antibiotic A-23187 (Calcimycin)
Martinez, Gregory R.,Grieco, Paul A.,Williams, Eric,Kanai, Ken-ichi,Srinivasan, C. V.
, p. 1436 - 1438 (1982)
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The chemistry of cyclic vinyl ethers. 6. Total synthesis of polyether ionophore antibiotics of the calcimycin (A-23187) class
Boeckman Jr., Robert K.,Charette, André B.,Asberom, Theodros,Johnston, Brian H.
, p. 5337 - 5353 (2007/10/02)
An extremely convergent (longest linear sequence, 16 steps), fully stereoselective, and potentially general synthesis of the antibiotic ionophores of the Calcimycin (A-23187) class was devised. The key steps involve a coupling reaction between the chiral nonracemic subunits dihydropyran 41 (as the α-lithio anion) and bromide 49. Subsequent acid-promoted cyclization directly produces the spirocyclic ring system found in the ionophore X-14885A (3). Alternatively, cyclopropanation of substituted vinyl ether 55 followed by acid treatment afforded the spiroketal 58 that was subsequently converted into the polyether ionophore Calcimycin (1) and also Cezomycin (2).
