Ionomycin

Names

[ Name ]:
Ionomycin

[Synonym ]:
10,16-Docosadienoic acid, 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-, (4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-
(4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-Trihydroxy-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-9-oxo-10,16-docosadienoic acid
Ionomycin
Ionomycin free acid,(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
Ionomycin,Free Acid,from Streptomyces conglbatus
MFCD00036890
Ionomycinefreeacid
Ionomycin from Streptomyces conglobatus
IONOMYCIN,STREPTOMYCES CONGLOBATUS
(4R,6S,8S,10Z,12R,14R,16E,18R,19R,20S,21S)-11,19,21-Trihydroxy-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-9-oxodocosa-10,16-dienoic acid
Ionomycin free acid
Ionomycin,Free Acid,Streptomyces conglobatus

Biological Activity

[Description]:

Ionomycin is a Calcium ionophore and an antibiotic produced by Streptomyces conglobatus ATCC 31005.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Research Areas >> Cancer

Research Areas >> Infection

[Target]

Calcium channel[1].

[In Vitro]

Ionomycin is a Calcium ionophore and an antibiotic produced by Streptomyces conglobatus ATCC 31005[1]. It is observed that LCLC 103H cells overexpressing the catalytic subunit of μ-calpain rapidly underwent cell death after treatment with ionomycin. The first signs of Ionomycin-induced cell death are detected 3 h after addition of the ionophore. Addition of 2 μM Ionomycin to LCLC 103H cells causes an instantaneous increase in intracellular Ca2+ concentration from 50 to 180 nM. Remarkably, calcium concentrations are raised transiently to 0.8-1.5 μM. DNA and protein analysis in Ionomycin-treated cultures revealed DNA fragmentation and PARP cleavage to an 85-kDa fragment typical of caspase-mediated apoptosis. Three hours after addition of ionomycin, the percentage of early apoptotic cells approximately doubles. Necrosis could be detected in ~1-5% of the Ionomycin treated cells as supported by simultaneously positive fluorescein labeling and propidium iodide uptake. Caspase activation in whole cells was followed by monitoring the increase in activity against Ac-DEVD-amc following Ionomycin treatment[2].

[References]

[1]. Liu C, et al. Characterization of ionomycin as a calcium ionophore. J Biol Chem. 1978 Sep 10;253(17):5892-4.

[2]. Gil-Parrado S, et al. Ionomycin-activated calpain triggers apoptosis. A probable role for Bcl-2 family members. J Biol Chem. 2002 Jul 26;277(30):27217-26.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.072 g/cm3

[ Boiling Point ]:
817.2ºC at 760 mmHg

[ Molecular Formula ]:
C₄₁H₇₂O₉

[ Molecular Weight ]:
709.00500

[ Flash Point ]:
235.2ºC

[ Exact Mass ]:
708.51800

[ PSA ]:
153.75000

[ LogP ]:
7.79960

[ Index of Refraction ]:
1.512

[ Storage condition ]:
−20°C

[ Water Solubility ]:
Soluble to 10 mM in Ethanol and to 10 mM in DMSO.

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NO0600000

CHEMICAL NAME :: Ionomycin

CAS REGISTRY NUMBER :: 56092-81-0

LAST UPDATED :: 199107

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C41-H70-O9

MOLECULAR WEIGHT :: 707.11

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 28 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 31,815,1978

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
36-36/37/39-27-26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
NO0650000

[ HS Code ]:
2941500000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2941500000

Articles

Ca²⁺ signals promote GLUT4 exocytosis and reduce its endocytosis in muscle cells.

Am. J. Physiol. Endocrinol. Metab. 307(2) , E209-24, (2014)

Elevating cytosolic Ca(2+) stimulates glucose uptake in skeletal muscle, but how Ca(2+) affects intracellular traffic of GLUT4 is unknown. In tissue, changes in Ca(2+) leading to contraction preclude ...

Regulation of T cell priming by lymphoid stroma.

PLoS ONE 6(11) , e26138, (2011)

The priming of immune T cells by their interaction with dendritic cells (DCs) in lymph nodes (LN), one of the early events in productive adaptive immune responses, occurs on a scaffold of lymphoid str...

Identification and characterization of IL-10/IFN-gamma-producing effector-like T cells with regulatory function in human blood.

J. Exp. Med. 206(5) , 1009-17, (2009)

Two subsets of natural and adaptive regulatory T (T reg) cells have been described, but the identity of adaptive type 1 regulatory (Tr1)-like cells in humans is unclear. We analyzed a subset of human ...

Related Compounds

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