U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C41H72O9
Molecular Weight 709.005
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of IONOMYCIN

SMILES

C[C@H](CCC(O)=O)C[C@H](C)C[C@H](C)C(=O)\C=C(/O)[C@H](C)C[C@H](C)C\C=C\[C@@H](C)[C@@H](O)[C@@H](C)[C@@H](O)C[C@@H]1CC[C@](C)(O1)[C@H]2CC[C@](C)(O2)[C@@H](C)O

InChI

InChIKey=PGHMRUGBZOYCAA-ADZNBVRBSA-N
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

HIDE SMILES / InChI

Molecular Formula C41H72O9
Molecular Weight 709.005
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 14 / 14
E/Z Centers 2
Optical Activity UNSPECIFIED

Description

Ionomycin is an ionophore produced by the bacterium Streptomyces conglobatus. The molecules act as a motile Ca2+ carrier and enhances Ca2+ influx by direct stimulation of store-regulated cation entry across biological membranes. It is highly specific for divalent cations. Ion selectivity is as follows: Ca2+ > Mg2+ >> Sr2+ = Ba2+ Binding of Sr2+ and Ba2+ is insignificant and binding to monovalent cations or rubidium is negligible. La2+ is also bound to some extent. Complexation with a cation is always in a 1:1 stoichiometry and pH-dependent. Essentially no binding of Ca2+ occurs below pH 7.0 and maximum binding takes place at pH 9.5. At the micromolar level, ionomycin can activate Ca2+/Calmodulin dependent kinase and phosphatase to stimulate gene expression. Ionomycin has been shown to induce central demyelination, inhibit adrenal bovine TREK-1 channels, and to regulate cell division of mature human B cells [1]. It is used to study the effects of calcium flux on endoplasmic reticulum (ER) stress, mitochodrial stress and intrinsic apoptosis mechanisms. It is also used to stimulate the intracellular production of the cytokines, interferon, perforin, IL-2, and IL-4 usually in conjunction with PMA.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Fifty male Sprague–Dawley rats weighing 200–250 g were maintained in SPF animal house under 12 h light/dark with water and food available ad libitum. After acclimation for a few days, six rats were selected for the normal group, the other remaining 44 animals were anesthetized with 7% chloral hydrate (0.5 ml/kg) and injected with 5 mkL 6-OHDA in the medial forebrain bundle (MFB). After two weeks of recovery, all rats were injected with apomorphine (0.05 mg/kg, s.c.) and observed for contralateral turns selecting animals with >7 turns/min for the studies. L-DOPA methyl ester (Sigma–Aldrich,12 mg/kg) plus benserazide (Sigma–Aldrich, 3 mg/kg) dissolved in saline was injected (i.p.) once a day for 21 consecutive days to induce AIMs. On the 11th day, the ionomycin group began to receive intrastriatal infusion of 1 mkg ionomycin (Cayman Chemical) dissolved in 4 mkl solution (5% DMSO and 5% tween-80 in saline) 30 min before LDOPA treatment
Route of Administration: Other
In Vitro Use Guide
T cells were cultured in 12 x 75 mm sterile serum and were stimulated with the Ionomycin with or without 10% monocytes. After 48 h of culture, the supernatants were collected and tested for IL-2 activity
Substance Class Chemical
Record UNII
54V905V6AT
Record Status Validated (UNII)
Record Version