A23187

drugbox
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

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CAS_number = 52665-69-7
ATC_prefix =
ATC_suffix =
ATC_supplemental =
PubChem =
DrugBank =
C=29|H=37|N=3|O=6
molecular_weight = 523.62 g/mol

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.

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. [cite web | url= http://www.online-medical-dictionary.org/A23187.asp?q=A23187| title=A23187| date=2006| publisher=Medical Dictionary Online| accessdate=2006-11-01] A23187 is most selective for Mn²⁺, somewhat less selective for Ca²⁺ and Mg²⁺, much less selective for Sr²⁺, and even less selective for Ba²⁺. [cite journal | last =Abbott | first = Bernard| authorlink = BJ Abbott| coauthors = D S Fukuda, D E Dorman, J L Occolowitz, M Debono, and L Farhner| title =Microbial transformation of A23187, a divalent cation ionophore antibiotic | journal =Antimicrobial Agents and Chemotherapy | volume = 16| issue =6 | pages = 808–812| publisher = | date = 1979| url =http://www.pubmedcentral.nih.gov/pagerender.fcgi?artid=352958&pageindex=1 | doi = | id = | accessdate = ] 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or S49, and Jurkat cells) and prevents it in others (e.g. cells dependent on interleukin 3 that have had the factor withdrawn).cite web | url= http://a23187.4mg.com/| title=A23187| accessdate=2006-11-01]

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. [ [http://cancerres.aacrjournals.org/cgi/content/full/60/13/3389 Liposomal Encapsulation of Topotecan Enhances Anticancer Efficacy in Murine and Human Xenograft Models] ]

Commercial availability

Commercially, A23187 is available as free acid, Ca²⁺ salt, and 4-Brominated analog. [ [http://www.fermentek.co.il/a23187FA.htm A23187 ] product page from Fermentek]

References

External links

* [http://www.agscientific.com/Virtual/VirtualPages/Item_Page_ALL_TYPES.asp?ItemCode=A1020&Item_Process_Mode=ADD A23187] from AG Scientific, another vendor
* [http://www.biomol.com/Online_Catalog/Online_Catalog/Products/Product_Detail/38/?categoryID=42&productID=133 A21387] from BIOMOL, a vendor's product page