{{Short description|Chemical compound}} {{Drugbox |Verifiedfields = changed |Watchedfields = changed |verifiedrevid = 461749035 |IUPAC_name = 5-(methylamino)-2-({(2''R'',3''R'',6''S'',8''S'',9''R'',11''R'')-3,9,11-trimethyl-8-[(1''S'')-1-methyl-2-oxo-2-(1''H''-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl}methyl)-1,3-benzoxazole-4-carboxylic acid |image = A23187.png |image_class = skin-invert-image
<!--Clinical data--> |tradename =
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 52665-69-7 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 37H9VM9WZL | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 11957499 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1256686 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 10131749 | smiles = CNc5ccc4oc(C[C@H]1O[C@@]3(CC[C@H]1C)O[C@H]([C@H](C)C(=O)c2ccc[nH]2)[C@H](C)C[C@H]3C)nc4c5C(=O)O | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C29H37N3O6/c1-15-10-11-29(17(3)13-16(2)27(38-29)18(4)26(33)20-7-6-12-31-20)37-22(15)14-23-32-25-21(36-23)9-8-19(30-5)24(25)28(34)35/h6-9,12,15-18,22,27,30-31H,10-11,13-14H2,1-5H3,(H,34,35)/t15-,16-,17-,18-,22-,27+,29+/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = HIYAVKIYRIFSCZ-CYEMHPAKSA-N
<!--Chemical data--> |C=29|H=37|N=3|O=6 }} '''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.<ref>{{cite web |url=http://www.online-medical-dictionary.org/A23187.asp?q=A23187 |title=A23187 |year=2006 |publisher=Medical Dictionary Online |access-date=2006-11-01 |archive-url=https://web.archive.org/web/20061210155944/http://www.online-medical-dictionary.org/A23187.asp?q=A23187 |archive-date=10 December 2006 |url-status=dead }}</ref> A23187 is most selective for Mn<sup>2+</sup>, somewhat less selective for Ca<sup>2+</sup> and Mg<sup>2+</sup>, much less selective for Sr<sup>2+</sup>, and even less selective for Ba<sup>2+</sup>.<ref>{{cite journal | vauthors = Abbott BJ, Fukuda DS, Dorman DE, Occolowitz JL, Debono M, Farhner L | title = Microbial transformation of A23187, a divalent cation ionophore antibiotic | journal = Antimicrobial Agents and Chemotherapy | volume = 16 | issue = 6 | pages = 808–812 | date = December 1979 | pmid = 119484 | pmc = 352958 | doi = 10.1128/aac.16.6.808 | authorlink = BJ Abbott }}</ref> The ionophore is used in laboratories to increase intracellular Ca<sup>2+</sup> 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).<ref name="A23">{{cite web|url=http://a23187.4mg.com/ |title=A23187 (Antibiotic A23187; Calcium Ionophore; Calcimycin) | work = Fermantek |access-date=2006-11-01 |archive-url=https://web.archive.org/web/20061103171331/http://a23187.4mg.com/ |archive-date=3 November 2006 |url-status=live }}</ref>
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.<ref name="pmid10910044">{{cite journal | vauthors = Tardi P, Choice E, Masin D, Redelmeier T, Bally M, Madden TD | title = Liposomal encapsulation of topotecan enhances anticancer efficacy in murine and human xenograft models | journal = Cancer Research | volume = 60 | issue = 13 | pages = 3389–93 | date = July 2000 | pmid = 10910044 | doi = | url = }}</ref>
In IVF field, Ca Ionophore can be used in case of low fertilization rate after ICSI procedure, particularly with Globozoospermia (Round Head sperm syndrome), Ca Ionophore will replace absence of sperm acrosome, and plays role in oocyte activation after ICSI. Recommended use is 0.5 microgram/ml twice for 10 min interrupted with fresh media with 30 min incubation, followed with regular injected eggs culture for IVF.<ref name="pmid25242978">{{cite journal | vauthors = Eftekhar M, Mohammadian F, Yousefnejad F, Khani P, Aflatoonian A | title = Effect of calcium ionophore on unfertilized oocytes after ICSI cycles | journal = Iranian Journal of Reproductive Medicine | volume = 10 | issue = 2 | pages = 83–6 | date = March 2012 | pmid = 25242978 | pmc = 4163267 | doi = | url = }}</ref>
==Biosynthesis== The core biosynthetic enzymes are thought to include 3 proteins for the biosynthesis of the α-ketopyrrole moiety, 5 for modular type I polyketide synthases for the spiroketal ring, 4 for the biosynthesis of 3-hydroxyanthranilic acid, an N-methyltransferase tailoring enzyme, and a type II thioesterase.<ref>{{cite journal | vauthors = Wu Q, Liang J, Lin S, Zhou X, Bai L, Deng Z, Wang Z | title = Characterization of the biosynthesis gene cluster for the pyrrole polyether antibiotic calcimycin (A23187) in Streptomyces chartreusis NRRL 3882 | journal = Antimicrobial Agents and Chemotherapy | volume = 55 | issue = 3 | pages = 974–982 | date = March 2011 | pmid = 21173184 | pmc = 3067094 | doi = 10.1128/AAC.01130-10 }}</ref>
==Commercial availability== Commercially, A23187 is available as free acid, Ca<sup>2+</sup> salt, and 4-brominated analog.<ref>{{cite web | url = http://www.fermentek.co.il/a23187FA.htm | title = A23187 | archive-url = https://web.archive.org/web/20060626050927/http://www.fermentek.co.il/a23187FA.htm | archive-date=June 26, 2006| work = Fermentek }}</ref>
== References == {{Reflist}}
== External links == * [https://web.archive.org/web/20070928105958/http://www.agscientific.com/Virtual/VirtualPages/Item_Page_ALL_TYPES.asp?ItemCode=A1020&Item_Process_Mode=ADD A23187] from AG Scientific, another vendor * [https://web.archive.org/web/20090906052243/http://www.biomol.com/Online_Catalog/Online_Catalog/Products/Product_Detail/38/?categoryID=42&productID=133 A21387] from BIOMOL, a vendor's product page * [http://www.bioaustralis.com/productorder.php?prodid=BIA-C1236&name=Calcimycin&searchtermf=Ionophore Calcimycin] from Bioaustralis, a vendor's product page
Category:Antibiotics Category:Ionophores Category:Benzoxazoles Category:Pyrroles Category:Uncouplers