Ionomycin free acid

calcium ionophore CAS# 56092-81-0

Ionomycin free acid

Catalog No. BCC7261----Order now to get a substantial discount!

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Chemical structure

Ionomycin free acid

3D structure

Chemical Properties of Ionomycin free acid

Cas No. 56092-81-0 SDF Download SDF
PubChem ID 6434517 Appearance Powder
Formula C41H72O9 M.Wt 709.01
Type of Compound N/A Storage Desiccate at -20°C
Solubility Ethanol : ≥ 10 mg/mL (14.10 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-[(5S)-5-[(5S)-5-[(1R)-1-hydroxyethyl]-5-methyloxolan-2-yl]-5-methyloxolan-2-yl]-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid
SMILES CC(CCC(=O)O)CC(C)CC(C)C(=O)C=C(C(C)CC(C)CC=CC(C)C(C(C)C(CC1CCC(O1)(C)C2CCC(O2)(C)C(C)O)O)O)O
Standard InChIKey PGHMRUGBZOYCAA-OJFQOPKISA-N
Standard InChI InChI=1S/C41H72O9/c1-25(21-29(5)34(43)24-35(44)30(6)22-27(3)20-26(2)14-15-38(46)47)12-11-13-28(4)39(48)31(7)36(45)23-33-16-18-41(10,49-33)37-17-19-40(9,50-37)32(8)42/h11,13,24-33,36-37,39,42-43,45,48H,12,14-23H2,1-10H3,(H,46,47)/b13-11+,34-24-/t25-,26-,27+,28-,29-,30+,31+,32-,33?,36+,37?,39-,40+,41+/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Ionomycin free acid

DescriptionCalcium ionophore; more specific than A23187.

Ionomycin free acid Dilution Calculator

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Ionomycin free acid Molarity Calculator

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Preparing Stock Solutions of Ionomycin free acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.4104 mL 7.0521 mL 14.1042 mL 28.2083 mL 35.2604 mL
5 mM 0.2821 mL 1.4104 mL 2.8208 mL 5.6417 mL 7.0521 mL
10 mM 0.141 mL 0.7052 mL 1.4104 mL 2.8208 mL 3.526 mL
50 mM 0.0282 mL 0.141 mL 0.2821 mL 0.5642 mL 0.7052 mL
100 mM 0.0141 mL 0.0705 mL 0.141 mL 0.2821 mL 0.3526 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Ionomycin free acid

Ionomycin is a selective and potent calcium ionophore, which acts as a motile Ca2+ carrier.by direct stimulation of store-regulated cation entry across biological membranes, ionomycin can effectively enhance Ca2+ influx.

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].

Clinical trial: One randomized, prospective, controlled study has been performed to analyze the effect of calcium ionophore solution on fertilization rate in patients with diminished ovarian reserve, which did not observe any differences in fertilization, clinical pregnancy, or ongoing pregnancy rates between the groups [3].

References:
[1] Liu C, Hermann TE.  Characterization of ionomycin as a calcium ionophore. J Biol Chem. 1978 Sep 10;253(17):5892-4.
[2] Heytens E, Soleimani R, Lierman S, De Meester S, Gerris J, Dhont M, Van der Elst J, De Sutter P.  Effect of ionomycin on oocyte activation and embryo development in mouse. Reprod Biomed Online. 2008 Dec;17(6):764-71.
[3] Caglar Aytac P, Kilicdag EB, Haydardedeoglu B, Simsek E, Cok T, Parlakgumus HA.  Can calcium ionophore "use" in patients with diminished ovarian reserve increase fertilization and pregnancy rates A randomized, controlled study. Fertil Steril. 2015 Nov;104(5):1168-74.

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References on Ionomycin free acid

Liberation of [3H]arachidonic acid and changes in cytosolic free calcium in fura-2-loaded human platelets stimulated by ionomycin and collagen.[Pubmed:3092807]

Biochem J. 1986 May 1;235(3):869-77.

Cytosolic Ca2+ levels and arachidonate liberation were investigated in platelets loaded with the fluorescent Ca2+ indicator dye fura-2, and labelled with [3H]arachidonate. Fura-2 was used in preference to quin2 because the latter interfered with [3H]arachidonate labelling of phospholipids. From a resting free Ca2+ level of around 100 nM, ionomycin (10-200 nM) evoked an instantaneous, concentration-dependent increase in cytosolic Ca2+ that only resulted in [3H]arachidonate liberation (up to 4-fold over control) at Ca2+ levels greater than 1 microM. Addition of collagen (10 micrograms/ml) evoked an elevation in Ca2+ up to 461 +/- 133 nM. These changes in Ca2+ were accompanied by a 2-4-fold elevation in [3H]arachidonate with depletion of [3H]phosphatidylcholine by 17 +/- 4% and [3H]phosphatidylinositol by 41 +/- 7%. Indomethacin (10 microM) reduced the elevation in Ca2+ by collagen to 115 +/- 18 nM but did not significantly inhibit the 2-4-fold increase in [3H]arachidonate. [3H]Phosphatidylcholine and [3H]phosphatidylinositol were decreased by 9 +/- 7% and 10 +/- 6%, respectively, with collagen in the presence of indomethacin. Stimulation of phosphoinositide turnover by collagen in the presence and absence of indomethacin was indicated by [32P]phosphatidate formation in cells prelabelled with [32P]Pi. This phosphatidate formation was decreased (75%) by the presence of indomethacin. In the presence of indomethacin, phorbol myristate acetate (20 nM) alone or in combination with ionomycin (30 nM) failed to stimulate arachidonate liberation despite a marked stimulation of aggregation. These results indicate that, whereas ionomycin requires Ca2+ in the microM range for arachidonate liberation, collagen, notably in the presence of indomethacin, does so at basal Ca2+ levels. The mechanisms underlying the regulation of arachidonate release by collagen are not clear, but do not appear to involve activation of protein kinase C, or an elevation of cytosolic free Ca2+.

Ionomycin causes activation of p38 and p42/44 mitogen-activated protein kinases in human neutrophils.[Pubmed:11401859]

Am J Physiol Cell Physiol. 2001 Jul;281(1):C350-60.

Many receptor-linked agents that prime or activate the NADPH oxidase in polymorphonuclear neutrophils (PMNs) elicit changes in cytosolic Ca2+ concentration and activate mitogen-activated protein (MAP) kinases. To investigate the role of Ca2+ in the activation of p38 and p42/44 MAP kinases, we examined the effects of the Ca2+-selective ionophore ionomycin on priming and activation of the PMN oxidase. Ionomycin caused a rapid rise in cytosolic Ca2+ that was due to both a release of cytosolic Ca2+ stores and Ca2+ influx. Ionomycin also activated (2 microM) and primed (20-200 nM) the PMN oxidase. Dual phosphorylation of p38 MAP kinase and phosphorylation of its substrate activating transcription factor-2 were detected at ionomycin concentrations that prime or activate the PMN oxidase, while dual phosphorylation of p42/44 MAP kinase and phosphorylation of its substrate Elk-1 were elicited at 0.2-2 microM. SB-203580, a p38 MAP kinase antagonist, inhibited ionomycin-induced activation of the oxidase (68 +/- 8%, P < 0.05) and tyrosine phosphorylation of 105- and 72-kDa proteins; conversely, PD-98059, an inhibitor of MAP/extracellular signal-related kinase 1, had no effect. Treatment of PMNs with thapsigargin resulted in priming of the oxidase and activation of p38 MAP kinase. Chelation of cytosolic but not extracellular Ca2+ completely inhibited ionomycin activation of p38 MAP kinase, whereas chelation of extracellular Ca2+ abrogated activation of p42/44 MAP kinase. These results demonstrate the importance of changes in cytosolic Ca2+ for MAP kinase activation in PMNs.

Cation transport and specificity of ionomycin. Comparison with ionophore A23187 in rat liver mitochondria.[Pubmed:6766939]

J Biol Chem. 1980 Apr 10;255(7):2735-9.

Based on the effects of ionomycin upon mitochondrial respiration, ionomycin was shown to be an effective ionophore for Ca2+ in rat liver mitochondria. The ionomycin-induced efflux of Ca2+ across the inner membrane was more sensitive to loading the mitochondria with Ca2+ than was efflux catalyzed by A23187. At saturating concentrations of Ca2+, the turnover number for ionomycin was 3- to 5-fold greater than that of A23187. Ionomycin catalyzed the efflux of mitochondrial Mg2+ at rates comparable to those observed with A23187. Ionomycin also mediated an efflux of K+ provided that the mitochondria were depleted of their endogenous divalent metal ions. The apparent turnover numbers for K+ efflux suggest that ionomycin is more specific for divalent metal ions than A23187.

Characterization of ionomycin as a calcium ionophore.[Pubmed:28319]

J Biol Chem. 1978 Sep 10;253(17):5892-4.

The ionophorous properties of a new antibiotic, ionomycin, have been studied. It was found that the antibiotic is capable of extracting calcium ion from the bulk of an aqueous phase into an organic phase. The antibiotic also acts as a mobile ion carrier to transport the cation across a solvent barrier. The divalent cation selectivity order for ionomycin as determined by ion competition experiments was found to be: Ca greater than Mg greater than Sr = Ba, where the binding of strontium and barium by the antibiotic is insignificant. The antibiotic also binds La3+ to some extent, but its complexation with monovalent alkali metal ions is negligible. Measurement of the binding of ionomycin with Ca2+ indicates that ionomycin complexes and transports calcium ion in a one to one stoichiometry.

Description

Ionomycin (SQ23377) is a potent, selective calcium ionophore and an antibiotic produced by Streptomyces conglobatus. Ionomycin (SQ23377) is highly specific for divalent cations (Ca>Mg>Sr=Ba). Ionomycin (SQ23377) promotes apoptosis. Ionomycin also induces the activation of protein kinase C (PKC).

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