56092-81-0

Basic information

• Product Name: IONOMYCIN
• Synonyms: (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;SQ-23377;Ionomycin,Free Acid,from Streptomyces conglbatus;(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;SQ 23377, EM 94;Ionomycin, free acid, from Streptomyces conglobatus;(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;IONOMYCIN
• CAS NO: 56092-81-0
• Molecular Formula: C41H72O9
• Molecular Weight: 709.01
• Product Categories: Chemical Structure Class;Core Bioreagents;Interferes with Cell Membrane Permeability (Ionophores)Antibiotics;Mechanism of Action;Spectrum of Activity;Calcium channel;Ion Channels;antibiotic;MiscellaneousMore...Close...;A - KResearch Essentials;Antibacterial;Antibiotics A to;Antibiotics by Application;Antibiotics G-MAntibiotics;AntibioticsAntibiotics;Antineoplastic and Immunosuppressive AntibioticsAntibiotics
• Mol File: 56092-81-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 817.2 °C at 760 mmHg
• Flash Point: 235.2 °C
• Appearance: Pale Yellow Oil
• Density: 1.072 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.512
• Storage Temp.: −20°C
• Solubility: Soluble to 10 mM in Ethanol and to 10 mM in DMSO.
• PKA: 4.77±0.10(Predicted)
• 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.
• BRN: 3642126
• CAS DataBase Reference: IONOMYCIN(CAS DataBase Reference)
• NIST Chemistry Reference: IONOMYCIN(56092-81-0)
• EPA Substance Registry System: IONOMYCIN(56092-81-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 36-36/37/39-27-26-24/25
• WGK Germany: 3
• RTECS: NO0650000
• F: 8-10
• HazardClass: 3
• Hazardous Substances Data: 56092-81-0(Hazardous Substances Data)

Usage

Description

Ionomycin, with the chemical formula (56092-81-0), is a highly selective nonfluorescent calcium (Ca2+) ionophore produced by Streptomyces conglobatus. It is characterized by its high affinity and selectivity for calcium ions, making it a potent Gram-positive antibiotic. Ionomycin is a very long-chain fatty acid with various substitutions, including methyl groups, hydroxy groups, and a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group. It is a white powder and is used in research to raise intracellular levels of Ca2+ and understand Ca2+ transport across biological membranes.

Uses

Used in Cell Biology Research:
Ionomycin is used as a universal calcium ionophore for studying the role of calcium regulation in cells. It helps researchers explore the effects of calcium flux on endoplasmic reticulum (ER) stress, mitochondrial stress, and intrinsic apoptosis mechanisms.
Used in Research on Calcium Transport:
Ionomycin is used as a mobile ion carrier for Ca2+ in research on Ca2+ transport across biological membranes. It is more effective than the antibiotic A23187 as a Ca++ ionophore.
Used in Neurobiology Research:
Ionomycin induces apoptotic degeneration of embryonic cortical neurons, making it a useful tool for studying neuronal degeneration and cell cycle arrest in mature Burkitt lymphoma cell lines.
Used in Immunology Research:
Ionomycin is used to stimulate the intracellular production of cytokines, such as interferon, perforin, IL-2, and IL-4, usually in conjunction with PMA. It also activates and primes neutrophil NADPH oxidase, which is essential for studying the immune response.
Used in Cancer Research:
Ionomycin has been shown to induce central demyelination, inhibit adrenal bovine TREK-1 channels, and regulate cell division of mature human B cells. It is also used to study the effects of calcium ions on various cancer cell lines, such as colon cancer cells.
Used in Chemical Research:
Ionomycin's chemical properties, such as its ability to complex with Ca2+ between pH 7 and 9.5, make it a valuable tool for studying the interactions between ions and biological molecules.

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].

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

InChI: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

Upstream product

• 110497-18-2 ionomycin methyl ester 
• 440104-25-6 benzoic acid 3-hydroxy-1-[5'-(1-hydroxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-20-methoxycarbonyl-2,4,8,10,14,16,18-heptamethyl-11,13-dioxo-eicos-5-enyl ester 
• 440104-13-2 [3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanal 
• 440104-12-1 [3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile 
• 440104-14-3 [3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-1-ol 
• 440104-18-7 [2E,6E]-9-benzenesulfonyl-3,7-dimethyl-nona-2,6-dien-1-ol 
• 440104-11-0 [2S,4R]-O-(4-toluene-sulfonate)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol 
• 440104-15-4 [3S,5R]-S-(1-phenyl-1H-tetrazol-5-yl)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-1-thiol 
• 440104-23-4 (2S)-4-(benzenesulfonyl)-2-[(2R,5S)-5-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-5-methyloxolan-2-yl]butan-2-ol 
• 440104-21-2 [2R,3S,6E]-toluene-4-sulfonic acid-9-benzenesulfonyl-2-(t-butyldimethylsiloxy)-3-hydroxy-3,7-dimethyl-non-6-enyl ester 
• 7586-22-3 methyl hydrogen meso-2,4-dimethylethylglutarate 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 37905-04-7 (2E,6E)-8-bromo-3,7-dimethylocta-2,6-dienyl acetate 
• 37905-03-6 8-hydroxygeranyl acetate 

Relevant articles and documents

Total Synthesis of Ionomycin Using Ring-Opening Strategies

(Matrix Presented) The total synthesis of the polyether antibiotic ionomycin, a calcium ionophore, is described. The synthesis demonstrates the utility of ring-opening methodologies as applied to the synthesis of polypropionate and deoxypolypropionate subunits, which are found in two of the four fragments in the synthesis.