Ionomycin Free Acid | CAS#56092-81-0 | CAS#56092-82-1

MedKoo Cat#: 540223 | Name: Ionomycin Free Acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ionomycin Free Acid is a Ca 2+ ionophore. Its depletion of intracellular Ca 2+ stores may be linked to the induction of apoptosis.

Chemical Structure

Ionomycin Free Acid

CAS#56092-81-0 (free acid)

Theoretical Analysis

MedKoo Cat#: 540223

Name: Ionomycin Free Acid

CAS#: 56092-81-0 (free acid)

Chemical Formula: C41H72O9

Exact Mass: 708.5176

Molecular Weight: 709.02

Elemental Analysis: C, 69.46; H, 10.24; O, 20.31

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 385.00	2 Weeks
10mg	USD 700.00	2 Weeks

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Related CAS #

56092-81-0 (free acid) 56092-82-1 (calcium)

Synonym

Ionomycin; Ionomycin free acid; SQ23377; SQ 23377;

IUPAC/Chemical Name

(4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-trihydroxy-22-((2S,5'S)-5'-((R)-1-hydroxyethyl)-2,5'-dimethyloctahydro-[2,2'-bifuran]-5-yl)-4,6,8,12,14,18,20-heptamethyl-9-oxodocosa-10,16-dienoic acid

InChi Key

PGHMRUGBZOYCAA-OJFQOPKISA-N

InChi Code

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

SMILES Code

C[C@@H](C[C@@H](C[C@@H](C(/C=C(O)/[C@@H](C[C@@H](C/C=C/[C@H]([C@@H](O)[C@H]([C@@H](O)CC1CC[C@@](C)(C2CC[C@@](C)([C@H](O)C)O2)O1)C)C)C)C)=O)C)C)CCC(O)=O

Appearance

A solution in ethanol

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ionomycin (SQ23377) is a potent, selective calcium ionophore and an antibiotic produced by Streptomyces conglobatus.

In vitro activity:

At higher PEF intensities (6.0 and 6.9 kV/cm), the addition of ionomycin significantly increased the percentage of IRE (irreversible electroporation) cells while decreasing the number of RE (reversible electroporation) cells. Reference: Biophys J. 2018 Jun 19;114(12):2875-2886. https://pubmed.ncbi.nlm.nih.gov/29925024/

In vivo activity:

BMSCs from Prrx1-alpl−/− mice treated with ionomycin showed increased osteogenic and decreased adipogenic differentiation (Fig. 7f–i). These results indicate that ALPL deficiency in BMSCs induces an age-related osteoporosis phenotype and that ionomycin treatment reversed this phenotype. Reference: Bone Res. 2020 Apr 26;8:19. https://pubmed.ncbi.nlm.nih.gov/32351759/

	Solvent	mg/mL	mM
Solubility
	DMF	2.5	3.53
	DMSO	4.3	5.99
	Ethanol	20.0	28.21
	Ethanol:PBS (pH 7.2) (1:10)	0.1	0.14

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 709.02 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Aiken EJ, Kilberg BG, Yu S, Hagness SC, Booske JH. Ionomycin-Induced Changes in Membrane Potential Alter Electroporation Outcomes in HL-60 Cells. Biophys J. 2018 Jun 19;114(12):2875-2886. doi: 10.1016/j.bpj.2018.05.018. PMID: 29925024; PMCID: PMC6026377. 2. Romera-Cárdenas G, Thomas LM, Lopez-Cobo S, García-Cuesta EM, Long EO, Reyburn HT. Ionomycin Treatment Renders NK Cells Hyporesponsive. PLoS One. 2016 Mar 23;11(3):e0150998. doi: 10.1371/journal.pone.0150998. PMID: 27007115; PMCID: PMC4805247. 3. Li B, He X, Dong Z, Xuan K, Sun W, Gao L, Liu S, Liu W, Hu C, Zhao Y, Shi S, Jin Y. Ionomycin ameliorates hypophosphatasia via rescuing alkaline phosphatase deficiency-mediated L-type Ca2+ channel internalization in mesenchymal stem cells. Bone Res. 2020 Apr 26;8:19. doi: 10.1038/s41413-020-0090-7. PMID: 32351759; PMCID: PMC7183511.

In vitro protocol:

In vivo protocol:

1. Li B, He X, Dong Z, Xuan K, Sun W, Gao L, Liu S, Liu W, Hu C, Zhao Y, Shi S, Jin Y. Ionomycin ameliorates hypophosphatasia via rescuing alkaline phosphatase deficiency-mediated L-type Ca2+ channel internalization in mesenchymal stem cells. Bone Res. 2020 Apr 26;8:19. doi: 10.1038/s41413-020-0090-7. PMID: 32351759; PMCID: PMC7183511.

1: Okudera M, Gojoubori T, Tsujino I, Asano M. Effect of ionomycin on interaction of calnexin with vesicular stomatitis virus glycoprotein is cell type-specific. J Oral Sci. 2015;57(4):305-12. doi: 10.2334/josnusd.57.305. PubMed PMID: 26666853. 2: Nakamura S, Nakanishi A, Takazawa M, Okihiro S, Urano S, Fukui K. Ionomycin-induced calcium influx induces neurite degeneration in mouse neuroblastoma cells: analysis of a time-lapse live cell imaging system. Free Radic Res. 2016;50(11):1214-1225. Epub 2016 Sep 29. PubMed PMID: 27573976. 3: Zhang Z, Zhang Y, Mou Z, Chu S, Chen X, He W, Guo X, Yuan Y, Takahashi M, Chen N. Tyrosine 402 phosphorylation of Pyk2 is involved in ionomycin-induced neurotransmitter release. PLoS One. 2014 Apr 9;9(4):e94574. doi: 10.1371/journal.pone.0094574. eCollection 2014. PubMed PMID: 24718602; PubMed Central PMCID: PMC3981813. 4: Zheng W, Feng X, Qiu L, Pan Z, Wang R, Lin S, Hou D, Jin L, Li Y. Identification of the antibiotic ionomycin as an unexpected peroxisome proliferator-activated receptor γ (PPARγ) ligand with a unique binding mode and effective glucose-lowering activity in a mouse model of diabetes. Diabetologia. 2013 Feb;56(2):401-11. doi: 10.1007/s00125-012-2777-9. Epub 2012 Nov 23. PubMed PMID: 23178929. 5: Nakazawa S, Shirae-Kurabayashi M, Otsuka K, Sawada H. Proteomics of ionomycin-induced ascidian sperm reaction: Released and exposed sperm proteins in the ascidian Ciona intestinalis. Proteomics. 2015 Dec;15(23-24):4064-79. doi: 10.1002/pmic.201500162. Epub 2015 Sep 25. PubMed PMID: 26223815. 6: Karlsson F, Hassan-Zahraee M. Quantification of Th1 and Th17 Cells with Intracellular Staining Following PMA/Ionomycin Stimulation. Curr Protoc Cytom. 2015 Jan 5;71:6.35.1-7. doi: 10.1002/0471142956.cy0635s71. PubMed PMID: 25559223. 7: Romera-Cárdenas G, Thomas LM, Lopez-Cobo S, García-Cuesta EM, Long EO, Reyburn HT. Ionomycin Treatment Renders NK Cells Hyporesponsive. PLoS One. 2016 Mar 23;11(3):e0150998. doi: 10.1371/journal.pone.0150998. eCollection 2016. PubMed PMID: 27007115; PubMed Central PMCID: PMC4805247. 8: Müller MS, Obel LF, Waagepetersen HS, Schousboe A, Bak LK. Complex actions of ionomycin in cultured cerebellar astrocytes affecting both calcium-induced calcium release and store-operated calcium entry. Neurochem Res. 2013 Jun;38(6):1260-5. doi: 10.1007/s11064-013-1021-4. Epub 2013 Mar 22. PubMed PMID: 23519933. 9: Vasilev F, Chun JT, Gragnaniello G, Garante E, Santella L. Effects of ionomycin on egg activation and early development in starfish. PLoS One. 2012;7(6):e39231. doi: 10.1371/journal.pone.0039231. Epub 2012 Jun 18. PubMed PMID: 22723970; PubMed Central PMCID: PMC3377674. 10: Chatila T, Silverman L, Miller R, Geha R. Mechanisms of T cell activation by the calcium ionophore ionomycin. J Immunol. 1989 Aug 15;143(4):1283-9. PubMed PMID: 2545785. 11: Zimmermann J, Radbruch A, Chang HD. A Ca(2+) concentration of 1.5 mM, as present in IMDM but not in RPMI, is critical for maximal response of Th cells to PMA/ionomycin. Eur J Immunol. 2015 Apr;45(4):1270-3. doi: 10.1002/eji.201445247. Epub 2015 Feb 17. PubMed PMID: 25545753; PubMed Central PMCID: PMC4407954. 12: Leis HJ, Windischhofer W. Ionomycin induces prostaglandin E2 formation in murine osteoblastic MC3T3-E1 cells via mechanisms independent of its ionophoric nature. Biochem Cell Biol. 2016 Jun;94(3):236-40. doi: 10.1139/bcb-2015-0148. Epub 2016 Feb 9. PubMed PMID: 27065246. 13: Kim HS, Lee JY, Jeong EJ, Yang CJ, Hyun SH, Shin T, Hwang WS. Effects of repetitive ionomycin treatment on in vitro development of bovine somatic cell nuclear transfer embryos. J Reprod Dev. 2012;58(1):132-9. Epub 2011 Dec 2. PubMed PMID: 22134064. 14: Morgan AJ, Jacob R. Ionomycin enhances Ca2+ influx by stimulating store-regulated cation entry and not by a direct action at the plasma membrane. Biochem J. 1994 Jun 15;300 ( Pt 3):665-72. PubMed PMID: 8010948; PubMed Central PMCID: PMC1138219. 15: Gao M, Jin W, Qian Y, Ji L, Feng G, Sun J. Effect of N-methyl-D-aspartate receptor antagonist on T helper cell differentiation induced by phorbol-myristate-acetate and ionomycin. Cytokine. 2011 Nov;56(2):458-65. doi: 10.1016/j.cyto.2011.06.022. Epub 2011 Jul 26. PubMed PMID: 21795061. 16: Li Q, Zhu X, Ishikura S, Zhang D, Gao J, Sun Y, Contreras-Ferrat A, Foley KP, Lavandero S, Yao Z, Bilan PJ, Klip A, Niu W. Ca²⁺ signals promote GLUT4 exocytosis and reduce its endocytosis in muscle cells. Am J Physiol Endocrinol Metab. 2014 Jul 15;307(2):E209-24. doi: 10.1152/ajpendo.00045.2014. Epub 2014 Jun 3. PubMed PMID: 24895284. 17: Ye L, Yang S. [Sirtuin 3 inhibits cardiomyocyte apoptosis by reducing cytochrome C release in myocardiac H9c2 cells with calcium overload]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2015 Aug;31(8):1031-5. Chinese. PubMed PMID: 26271974. 18: Ye Y, Zhang Y, Lu X, Huang X, Zeng X, Lai X, Zeng Y. The anti-inflammatory effect of the SOCC blocker SK&F 96365 on mouse lymphocytes after stimulation by Con A or PMA/ionomycin. Immunobiology. 2011 Sep;216(9):1044-53. doi: 10.1016/j.imbio.2011.03.001. Epub 2011 Mar 12. PubMed PMID: 21470712. 19: Phillippe M, Chien EM, Freij M, Saunders T. Ionomycin-stimulated phasic myometrial contractions. Am J Physiol. 1995 Oct;269(4 Pt 1):E779-85. PubMed PMID: 7485495. 20: Rascado Tda S, Martins LR, Minto BW, de Sá Lorena SE, Landim-Alvarenga Fda C. Parthenogenetic development of domestic cat oocytes treated with ionomycin, cycloheximide, roscovitine and strontium. Theriogenology. 2010 Sep 1;74(4):596-601. doi: 10.1016/j.theriogenology.2010.03.010. Epub 2010 May 7. PubMed PMID: 20452001.