Ionomycin

Ionomycin
Names
	IUPAC name (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-19,21-Dihydroxy-22-{(2S,2′R,5S,5′S)-5′-[(1R)-1-hydroxyethyl]-2,5′-dimethyloctahydro-2,2′-bifuran-5-yl}-4,6,8,12,14,18,20-heptamethyl-11-oxido-9-oxodocosa-10,16-dienoic acid
Identifiers
CAS Number	56092-81-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL501617 ; ChEMBL1222121 ;
ChemSpider	5288579 ;
ECHA InfoCard	100.121.228
PubChem CID	6912226;
UNII	54V905V6AT ;
	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 Key: PGHMRUGBZOYCAA-ADZNBVRBSA-N ; InChI=1/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 Key: PGHMRUGBZOYCAA-ADZNBVRBBY;
	SMILES C[C@H](CCC(=O)O)C[C@H](C)C[C@H](C)C(=O)/C=C(/[C@H](C)C[C@H](C)C/C=C/[C@@H](C)[C@H]([C@@H](C)[C@H](C[C@@H]1CC[C@@](O1)(C)[C@H]2CC[C@@](O2)(C)[C@@H](C)O)O)O)\O;
Properties
Chemical formula	C41H72O9
Molar mass	709.0050 g/mol
Solubility	insoluble in water, soluble in fats, DMSO,[1] heptane and hexane[2]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Ionomycin is an ionophore and an antibiotic that binds calcium ions (Ca²⁺) in a ratio 1:1. It is produced by the bacterium Streptomyces conglobatus.[3] It binds also other divalent cations like magnesium and cadmium, but binds Ca²⁺ preferably.[1][2]

It has 14 chiral centers. Its β-diketone and carboxylic acid group form a chelate with calcium.[3]

It was extracted in 1978 and the complete structure was elucidated in 1979.[2][3]

It is used in research to raise the intracellular calcium level (Ca²⁺) and as a research tool to understand Ca²⁺ transport across biological membranes.[3]

Ionomycin is often sold as a free acid, or as a Ca²⁺ salt. Both are insoluble in water, but soluble in fats and DMSO. Because of their fat solubility, they bind to proteins like albumin, which may interfere with their use in studies involving blood.[1]

References

Kao J, et al. (2010). "Practical aspects of measuring intracellular calcium signals with fluorescent indicators". Methods in Cell Biology. 99: 113–152. doi:10.1016/B978-0-12-374841-6.00005-0. ISBN 9780123748416. ISSN 0091-679X. PMID 21035685.
Toeplitz BK, et al. (1979). "Structure of ionomycin - a novel diacidic polyether antibiotic having high affinity for calcium ions". Journal of the American Chemical Society. 101 (12): 3344–3353. doi:10.1021/ja00506a035. ISSN 0002-7863.
Lautens M, et al. (2002). "Total synthesis of ionomycin using ring-opening strategies". Organic Letters. 4 (11): 1879–1882. doi:10.1021/ol025872f. ISSN 1523-7060. PMID 12027637.

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[:1-1] Kao J, et al. (2010). "Practical aspects of measuring intracellular calcium signals with fluorescent indicators". Methods in Cell Biology. 99: 113–152. doi:10.1016/B978-0-12-374841-6.00005-0. ISBN 9780123748416. ISSN 0091-679X. PMID 21035685.

[:2-2] Toeplitz BK, et al. (1979). "Structure of ionomycin - a novel diacidic polyether antibiotic having high affinity for calcium ions". Journal of the American Chemical Society. 101 (12): 3344–3353. doi:10.1021/ja00506a035. ISSN 0002-7863.

[:0-3] Lautens M, et al. (2002). "Total synthesis of ionomycin using ring-opening strategies". Organic Letters. 4 (11): 1879–1882. doi:10.1021/ol025872f. ISSN 1523-7060. PMID 12027637.