Valinomycin

Names

[ CAS No. ]:
2001-95-8

[ Name ]:
Valinomycin

[Synonym ]:
(3S,6S,9R,12R,15S,18S,21R,24R,27S,30S,33R,36R)-6,18,30-trimethyl-3,9,12,15,21,24,27,33,36-nona(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone
Valinomycin
antibioticn-329b
valinomicin
1,7,13,19,25,31-Hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone, 6,18,30-trimethyl-3,9,12,15,21,24,27,33,36-nonakis(1-methylethyl)-, (3S,6S,9R,12R,15S,18S,21R,24R,27S,30S,33R,36R)-
EINECS 217-896-6
Valinomycin,Cyclo(D-α-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl-D-α-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl-D-α-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl)
Cyclo(D-α-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl-D-α-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl-D-α-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl)
(3R,6R,9S,12S,15R,18R,21S,24S,27R,30R,33S,36S)-3,6,9,15,18,21,27,30,33-Nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone
BU 226 hydrochloride
Cyclo(D-a-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl-D-a-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl-D-a-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl)
MFCD00005114

Biological Activity

[Description]:

Valinomycin (NSC 122023) is a cyclic depsipeptide antibiotic first isolated from Streptomyces fulvissimus, act as a potassium selective ionophore. Valinomycin (NSC 122023) inhibits lymphocyte proliferation by its effects on the cell membrane, and induces apoptosis in CHO cells[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Others

Signaling Pathways >> Others >> Others

[References]

[1]. Daniele RP, et al. A potassium ionophore (valinomycin) inhibits lymphocyte proliferation by its effects on the cell membrane. Proc Natl Acad Sci U S A. 1976 Oct;73(10):3599-602.

[2]. Tosteson DC, et al. The effect of valinomycin on potassium and sodium permeability of HK and LK sheep red cells. J Gen Physiol. 1967 Dec;50(11):2513-25.

[3]. Abdalah R, et al. Valinomycin-induced apoptosis in Chinese hamster ovary cells. Neurosci Lett. 2006 Sep 11;405(1-2):68-73.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
1333.9±65.0 °C at 760 mmHg

[ Melting Point ]:
186-190ºC

[ Molecular Formula ]:
C₅₄H₉₀N₆O₁₈

[ Molecular Weight ]:
1111.322

[ Flash Point ]:
760.5±34.3 °C

[ Exact Mass ]:
1110.631104

[ PSA ]:
332.40000

[ LogP ]:
-2.08

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.449

[ Storage condition ]:
2~8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YV9468000

CHEMICAL NAME :: Valinomycin

CAS REGISTRY NUMBER :: 2001-95-8

BEILSTEIN REFERENCE NO. :: 0078657

LAST UPDATED :: 199701

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C54-H90-N6-O18

MOLECULAR WEIGHT :: 1111.50

WISWESSER LINE NOTATION :: T-36-MV DOV GMV JOV MMV POV SMV VOV B&MV E&OV H&MV K&OVTJ C1 FY1&1 IY1&1 LY1&1 O1 RY1&1 UY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 8,451,1985

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 800 ug/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 8,451,1985

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2500 ug/kg

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

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,325,1978

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 390 ug/kg

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

REFERENCE :: NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. (Bethesda, MD 20205) Volume(issue)/page/year: JAN1986

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4140 ug/kg

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

REFERENCE :: ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 12,482,1962

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 180 ug/kg

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

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 46,5518,1986

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 5 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 8,451,1985

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300 + H310

[ Precautionary Statements ]:
P264-P280-P301 + P310-P302 + P350-P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R27/28

[ Safety Phrases ]:
S28;S45;S36/S37

[ RIDADR ]:
UN 2811 6

[ WGK Germany ]:
3

[ RTECS ]:
YV9468000

[ Hazard Class ]:
6.1(a)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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Related Compounds

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