| Revision as of 11:02, 21 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 461498364 of page A23187 for the Chem/Drugbox validation project (updated: 'ChEMBL'). |
Latest revision as of 15:42, 1 January 2025 edit Minnsurfur (talk | contribs)79 editsm →Actions and uses |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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|Verifiedfields = changed |
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| verifiedrevid = 460442039 |
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|Watchedfields = changed |
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| IUPAC_name = 5-(methylamino)-2-({(2''R'',3''R'',6''S'',8''S'',9''R'',11''R'')-3,9,11-trimethyl-8--1,7-dioxaspiroundec-2-yl}methyl)-1,3-benzoxazole-4-carboxylic acid |
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|verifiedrevid = 461749035 |
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| image = A23187.png |
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|IUPAC_name = 5-(methylamino)-2-({(2''R'',3''R'',6''S'',8''S'',9''R'',11''R'')-3,9,11-trimethyl-8--1,7-dioxaspiroundec-2-yl}methyl)-1,3-benzoxazole-4-carboxylic acid |
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|image = A23187.png |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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|tradename = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 52665-69-7 |
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| CAS_number = 52665-69-7 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ATC_prefix = |
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| UNII = 37H9VM9WZL |
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| ATC_suffix = |
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| ATC_supplemental = |
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| ATC_suffix = |
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| ATC_supplemental = |
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| PubChem = 11957499 |
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| PubChem = 11957499 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 1256686 --> |
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| ChEMBL = 1256686 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10131749 |
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| ChemSpiderID = 10131749 |
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| SMILES = O=C(O)c1c(NC)ccc2oc(nc12)C5O3(O((C)C3C)(C(=O)c4cccn4)C)CC5C |
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| smiles = CNc5ccc4oc(C1O3(CC1C)O((C)C(=O)c2ccc2)(C)C3C)nc4c5C(=O)O |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/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 |
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| InChIKey = HIYAVKIYRIFSCZ-CYEMHPAKBV |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = HIYAVKIYRIFSCZ-CYEMHPAKSA-N |
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| StdInChIKey = HIYAVKIYRIFSCZ-CYEMHPAKSA-N |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=29 | H=37 | N=3 | O=6 |
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|C=29|H=37|N=3|O=6 |
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| molecular_weight = 523.62 g/mol |
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'''A23187''' is a mobile ] that forms stable complexes with divalent cations (]s with a charge of +2). A23187 is also known as '''Calcimycin''', '''Calcium ]''', '''Antibiotic A23187''' and '''Calcium ] A23187'''. It is produced at ] of '']'' '']''. |
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==Actions and uses== |
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A23187 has ] properties against ] ] and ]. It also acts as a divalent cation ], allowing these ions to cross ]s, 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 ] and ], much less selective for ], and even less selective for ].<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 ]s. It also uncouples ], the process cells use to synthesize ], which they use for energy. In addition, A23187 inhibits mitochondrial ] activity. A23187 also induces apoptosis in some cells (e.g. mouse ] cell line, or S49, and ]) and prevents it in others (e.g. cells dependent on ] 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> |
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] (Canada) reported an innovative application of A23187. Inex used A23187 as a molecular tool in order to make artificial ] loaded with anti-] drugs such as ].<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> |
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In ] field, Ca Ionophore can be used in case of low fertilization rate after ICSI procedure, particularly with ] (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> |
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==Biosynthesis== |
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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> |
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==Commercial availability== |
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Commercially, A23187 is available as free ], 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 = ] }}</ref> |
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== References == |
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{{Reflist}} |
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== External links == |
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* from ], another vendor |
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* from BIOMOL, a vendor's product page |
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* from Bioaustralis, a vendor's product page |
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