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 Streptomyceschartreusensis.
A23187 has antibiotic properties against gram positivebacteria 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or S49, and Jurkat cells) and prevents it in others (e.g. cells dependent on interleukin 3 that have had the factor withdrawn).[3]
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.[5]
Biosynthesisedit
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.[6]
Commercial availabilityedit
Commercially, A23187 is available as free acid, Ca2+ salt, and 4-brominated analog.[7]
Referencesedit
^. Medical Dictionary Online. 2006. Archived from the original on 10 December 2006. Retrieved 2006-11-01.
^Abbott BJ, Fukuda DS, Dorman DE, Occolowitz JL, Debono M, Farhner L (December 1979). "Microbial transformation of A23187, a divalent cation ionophore antibiotic". Antimicrobial Agents and Chemotherapy. 16 (6): 808–812. doi:10.1128/aac.16.6.808. PMC352958. PMID 119484.
^"A23187 (Antibiotic A23187; Calcium Ionophore; Calcimycin)". Fermantek. from the original on 3 November 2006. Retrieved 2006-11-01.
^Tardi P, Choice E, Masin D, Redelmeier T, Bally M, Madden TD (July 2000). "Liposomal encapsulation of topotecan enhances anticancer efficacy in murine and human xenograft models". Cancer Research. 60 (13): 3389–93. PMID 10910044.
^Eftekhar M, Mohammadian F, Yousefnejad F, Khani P, Aflatoonian A (March 2012). "Effect of calcium ionophore on unfertilized oocytes after ICSI cycles". Iranian Journal of Reproductive Medicine. 10 (2): 83–6. PMC4163267. PMID 25242978.
^Wu Q, Liang J, Lin S, Zhou X, Bai L, Deng Z, Wang Z (March 2011). "Characterization of the biosynthesis gene cluster for the pyrrole polyether antibiotic calcimycin (A23187) in Streptomyces chartreusis NRRL 3882". Antimicrobial Agents and Chemotherapy. 55 (3): 974–982. doi:10.1128/AAC.01130-10. PMC3067094. PMID 21173184.
^. Fermentek. Archived from the original on June 26, 2006.
External linksedit
from AG Scientific, another vendor
from BIOMOL, a vendor's product page
Calcimycin from Bioaustralis, a vendor's product page
November 30, 2023
a23187, mobile, carrier, that, forms, stable, complexes, with, divalent, cations, ions, with, charge, also, known, calcimycin, calcium, ionophore, antibiotic, calcium, ionophore, produced, fermentation, streptomyces, chartreusensis, identifiersiupac, name, met. 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 A23187IdentifiersIUPAC name 5 methylamino 2 2R 3R 6S 8S 9R 11R 3 9 11 trimethyl 8 1S 1 methyl 2 oxo 2 1H pyrrol 2 yl ethyl 1 7 dioxaspiro 5 5 undec 2 yl methyl 1 3 benzoxazole 4 carboxylic acidCAS Number52665 69 7 YPubChem CID11957499ChemSpider10131749 YUNII37H9VM9WZLChEMBLChEMBL1256686 NCompTox Dashboard EPA DTXSID1040405ECHA InfoCard100 052 786Chemical and physical dataFormulaC 29H 37N 3O 6Molar mass523 630 g mol 13D model JSmol Interactive imageSMILES 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 OInChI InChI 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 YKey HIYAVKIYRIFSCZ CYEMHPAKSA N Y N Y what is this verify Contents 1 Actions and uses 2 Biosynthesis 3 Commercial availability 4 References 5 External linksActions and uses editA23187 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 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 5 Biosynthesis editThe core biosynthetic enzymes are thought to include 3 proteins for the biosynthesis of the a 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 6 Commercial availability editCommercially A23187 is available as free acid Ca2 salt and 4 brominated analog 7 References edit A23187 Medical Dictionary Online 2006 Archived from the original on 10 December 2006 Retrieved 2006 11 01 Abbott BJ Fukuda DS Dorman DE Occolowitz JL Debono M Farhner L December 1979 Microbial transformation of A23187 a divalent cation ionophore antibiotic Antimicrobial Agents and Chemotherapy 16 6 808 812 doi 10 1128 aac 16 6 808 PMC 352958 PMID 119484 A23187 Antibiotic A23187 Calcium Ionophore Calcimycin Fermantek Archived from the original on 3 November 2006 Retrieved 2006 11 01 Tardi P Choice E Masin D Redelmeier T Bally M Madden TD July 2000 Liposomal encapsulation of topotecan enhances anticancer efficacy in murine and human xenograft models Cancer Research 60 13 3389 93 PMID 10910044 Eftekhar M Mohammadian F Yousefnejad F Khani P Aflatoonian A March 2012 Effect of calcium ionophore on unfertilized oocytes after ICSI cycles Iranian Journal of Reproductive Medicine 10 2 83 6 PMC 4163267 PMID 25242978 Wu Q Liang J Lin S Zhou X Bai L Deng Z Wang Z March 2011 Characterization of the biosynthesis gene cluster for the pyrrole polyether antibiotic calcimycin A23187 in Streptomyces chartreusis NRRL 3882 Antimicrobial Agents and Chemotherapy 55 3 974 982 doi 10 1128 AAC 01130 10 PMC 3067094 PMID 21173184 A23187 Fermentek Archived from the original on June 26 2006 External links editA23187 from AG Scientific another vendor A21387 from BIOMOL a vendor s product page Calcimycin from Bioaustralis a vendor s product page Retrieved from https en wikipedia org w index php title A23187 amp oldid 1186391070, wikipedia, wiki, book, books, library,
