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
CAS_number = 52665-69-7
molecular_weight = 523.62 g/mol
A23187 is a mobile
ion-carrierthat 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 StreptomycesChartreusensis.
Actions and uses
antibioticproperties against gram positive bacteriaand 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 triphosphatewhich they use for energy. In addition, A23187 inhibits mitochondrial ATPaseactivity. A23187 also induces apoptosis in some cells (e.g. mouse lymphomacell line, or S49, and Jurkat cells) and prevents it in others (e.g. cells dependent on interleukin 3that have had the factor withdrawn).cite web | url= http://a23187.4mg.com/| title=A23187| accessdate=2006-11-01] Inex Pharmaceuticals Corporation(Canada) reported an innovative application of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 liposomesloaded with anti- cancerdrugs 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] ]
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]
* [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
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