| Identification | Back Directory | [Name]
IONOMYCIN | [CAS]
56092-81-0 | [Synonyms]
EM 94
SQ-23377
IONOMYCIN
SQ 23377, EM 94
Ionomycinefreeacid
IONOMYCIN (SQ23377)
IONOMYCIN USP/EP/BP
Ionomycin Free Acid (85%)
IONOMYCIN, STREPTOMYCES CONGLOBATUS
Ionomycin from Streptomyces conglobatus
Ionomycin, Free Acid, Streptomyces conglobatus
Ionomycin, 98.5%, from Streptomyces conglobatus
Ionomycin, free acid, from Streptomyces conglobatus
Ionomycin,Free Acid,from Streptomyces conglbatus
ionomycin calcium salt from streptomyces conglobatus
Ionomycin, Free Acid, Streptomyces conglobatus - CAS 56092-81-0 - Calbiochem
Ionomycin, Free Acid, Streptomyces conglobatus in Solution - CAS 56092-81-0 - Calbiochem
(4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-Trihydroxy-4,6,8,12,14,18,20-heptamethyl-22-((2S,2'R,5S,5'S)-octahyd
(4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-Trihydroxy-4,6,8,12,14,18,20-heptamethyl-22-[(2S,2'R,5S,5'S)-octahydro-5'-[(1R)-1-hydroxyethyl]-2,5'-dimethyl[2,2'-bifuran]-5-yl]-9-oxo-10,16-docosadienoicacid
(4R,6S,8S,10Z,12R,14R,16E,18S,19S,20R,21S)-11,19,21-Trihydroxy-22-{(2S,2'S,5S,5'R)-5'-[(1S)-1-hydroxyethyl]-2,5'-dimethyloctahydro-2,2'-bifuran-5-yl}-4,6,8,12,14,18,20-heptamethyl-9-oxo-10,16-docosadi enoic acid
(4R,6S,8R,12R,14S,18S,19R,20R,21R)-19,21-Dihydroxy-22-[(2R,5R)-5-[(2R,5S)-5-(1-hydroxyethyl)-5-methyl-oxolan-2-yl]-5-methyl-oxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-11-oxido-9-oxo-docosa-10,16-dienoate calcium salt
10,16-Docosadienoic acid, 11,19,21-trihydroxy-4,6,8,12,14,18,20-heptamethyl-22-[(2S,2'R,5S,5'S)-octahydro-5'-[(1R)-1-hydroxyethyl]-2,5'-dimethyl[2,2'-bifuran]-5-yl]-9-oxo-, (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)- | [Molecular Formula]
C41H72O9 | [MDL Number]
MFCD06798385 | [MOL File]
56092-81-0.mol | [Molecular Weight]
709.01 |
| Chemical Properties | Back Directory | [Boiling point ]
817.2±65.0 °C(Predicted) | [density ]
1.072±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Soluble to 10 mM in Ethanol and to 10 mM in DMSO. | [form ]
Waxy solid | [pka]
4.77±0.10(Predicted) | [color ]
Yellow | [BRN ]
3642126 | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
| Hazard Information | Back Directory | [Description]
Ionomycin (56092-81-0) is a highly selective nonfluorescent calcium (Ca2+) ionophore.1 Induces a rapid rise in cytosolic Ca2+ in human neutrophils which is due to both release from cytosolic Ca2+ stores as well as Ca2+ influx.2 It activates (2 μM) and primes (20-200 nM) neutrophil NADPH oxidase2. Down regulates beta-catenin/Tcf signaling in a colon cancer cell line via suppressing the binding of Tcf to its specific DNA-binding site.3 In rat hepatoma cells, sub-lethal ionomycin activates the stress response by activating SAPK/JNK and HSF/HSE interaction leading to upregulation of HSP70 biosynthesis.4 | [Chemical Properties]
White powder | [Uses]
Ionomycin is more effective than A23187 as a Ca++ionophore.
Ionomycin is used in research on Ca++ transport across biological membranes;
Ionomycin induces apoptotic degeneration of embryonic cortical neurons | [Uses]
Ionomycin was isolated from Streptomyces conglobatus as a potent Gram positive antibiotic . During isolation, it was recognised that ionomycin exhibits a very high affinity and selectivity for calcium ions, suggesting the metabolite acts as a calcium ionophore. More recently, ionomycin has been used in cell biology as a universal calcium ionophore to explore the role of calcium regulation in the cell. | [Definition]
ChEBI: A very long-chain fatty acid that is docosa-10,16-dienoic acid which is substituted by methyl groups at positions 4, 6, 8, 12, 14, 18 and 20, by hydroxy groups at positions 11, 19 and 21, and by a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group at
osition 21. An ionophore produced by Streptomyces conglobatus, it is used in research to raise the intracellular level of Ca2+ and as a research tool to understand Ca2+ transport across biological memb
anes. | [General Description]
Highly specific for divalent cations (Ca2+ > Mg2+ >> Sr2+ = Ba2+). More effective than antibiotic A23187 as a mobile ion carrier for Ca2+. Complexes with Ca2+ between pH 7 and 9.5, causing significant absorption in the UV range; however, in contrast to A23187 (Cat. No. 100105), it is not fluorescent. Useful for studies of Ca2+ transport across biological membranes and measurement of cytoplasmic free Ca2+. Induces apoptotic neuronal degeneration in embryonic cortical neurons. Also induces cell cycle arrest in the G1 interval of mature Burkitt lymphoma cell lines. | [Biological Activity]
Calcium ionophore; more specific than A23187 (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]-4-benzoxazolecarboxylic acid ). | [Biochem/physiol Actions]
Cell permeable: yes | [in vitro]
calcium ion can be extracted by ionomycin fom the queous phase into the organic phase. ionomycin also acts as a mobile ion carrier, which transports the cation across a solvent barrier [1]. | [in vivo]
efficiency of ionomycin on oocyte activation and subsequent development was evaluated, which identified ionomycin as an efficient activator at the concentation of 10 μmol/l. with a second exposure to 5 μmol/l ionomycin on blastocyst development, an improved effect was found. no adverse effects of ionomycin on mouse embryo development were identified [2]. | [storage]
-20°C | [References]
1) Kaufmann et al., (1980), Cation transport and specificity of ionomycin. Comparison with ionophore A23187 in rat liver mitochondria; J. Biol. Chem. 255 2735
2) Elzi et al., (2001), Ionomycin causes activation of p38 and p42/44 mitogen-activated protein kinases in human neutrophils; Am. J. Physiol. Cell Physiol. 281 C350
3) Park et al., (2005), Ionomycin downregulates beta-catenin/tcf signaling in colon cancer cell line; Carcinogenesis, 26 1929
4) Sreedhar and Srinivas (2002), Activation of stress response by ionomycin in rat hepatoma cells; J. Cell Biochem., 86 154 |
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