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A23187



A23187
Systematic (IUPAC) name
5-methylamino-2-(2S,3R,5R,8S,9S)-

3,5,9-trimethyl-2-(1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl)- 1,7-dioxaspiro(5.5)undecan-8-yl)methyl)benzooxazole-4-carboxylic acid

Identifiers
CAS number 52665-69-7
ATC code  ?
PubChem  ?
Chemical data
Formula C29H37N3O6 
Mol. mass 523.62 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

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Legal status
Routes  ?

A23187 is a mobile ion-carrier that forms stable complexes with divalent cations (ions with a charge of +2). A23187 is also known as Calcimycin, Calcium Ionophore, Antibiotic A23187 and Calcium Ionophore A23187. It is produced at fermentation of Streptomyces Chartreusensis.

Additional recommended knowledge

Actions and uses

A23187 has antibiotic properties against gram positive bacteria and fungi. It also acts as a divalent cation ionophore, allowing these ions to cross cell membranes, which are usually impermeable to them.[1] A23187 is most selective for Mn2+, somewhat less selective for Ca2+ and Mg2+, much less selective for Sr2+, and even less selective for Ba2+.[2] The ionophore is used in laboratories to increase intracellular Ca2+ levels in intact cells. It also uncouples oxidative phosphorylation, the process cells use to synthesize Adenosine triphosphate which they use for energy. In addition, A23187 inhibits mitochondrial ATPase activity. A23187 also induces apoptosis in some cells (e.g. mouse lymphoma cell line, or S49, and Jurkat cells) and prevents it in others (e.g. cells dependent on interleukin 3 that have had the factor withdrawn).[3]

Inex Pharmaceuticals Corporation (Canada) reported an innovative application of A23187. Inex used A23187 as a molecular tool in order to make artificial liposomes loaded with anti-cancer drugs such as Topotecan.[4]

Commercial availability

Commercially, A23187 is available as free acid, Ca2+ salt, and 4-Brominated analog.

References

  1. ^ A23187. Medical Dictionary Online (2006). Retrieved on 2006-11-01.
  2. ^ Abbott, Bernard; D S Fukuda, D E Dorman, J L Occolowitz, M Debono, and L Farhner (1979). "Microbial transformation of A23187, a divalent cation ionophore antibiotic". Antimicrobial Agents and Chemotherapy 16 (6): 808–812.
  3. ^ A23187. Retrieved on 2006-11-01.
  4. ^ Liposomal Encapsulation of Topotecan Enhances Anticancer Efficacy in Murine and Human Xenograft Models
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "A23187". A list of authors is available in Wikipedia.
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