VALINOMYCIN

Product Name: VALINOMYCIN
CAS No.: 2001-95-8
Chemical Name: VALINOMYCIN
Synonyms: valinomicin;nsc122023;valamycin;-valyl)[qr];VALINOMYCIN;nsc122023[qr];valinomicin[qr];VALINOMYCIN 99%;Valinomycin,90%;Valinomycin,96%
CBNumber: CB7199194
Molecular Formula: C54H90N6O18
Formula Weight: 1111.32
MOL File: 2001-95-8.mol

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VALINOMYCIN Property

Melting point:: 187-190 °C
alpha: D20 +31.0° (c = 1.6 in benzene)
Boiling point:: 821.74°C (rough estimate)
Density: 1.060
refractive index: 1.6400 (estimate)
Flash point:: 87℃
storage temp.: 2-8°C
solubility: DMSO: ≥10 mg/mL
form: solid
pka: 11.32±0.70(Predicted)
color: white
optical activity: [α]20/D +32±2°, c = 1.6% in benzene
Water Solubility: Soluble in DMSO at 10mg/ml. Insoluble in water
Merck: 13,9976
BRN: 78657
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
EPA Substance Registry System: Valinomycin (2001-95-8)

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Safety

Hazard Codes: Xn,T,T+,Xi
Risk Statements: 27/28-36/37/38-21/22
Safety Statements: 36-45-36/37-28-37/39-26
RIDADR: UN 2811 6.1/PG 1
WGK Germany: 3
RTECS: YV9468000
F: 10-18-21
TSCA: Yes
HazardClass: 6.1(a)
PackingGroup: I
HS Code: 29419090
Hazardous Substances Data: 2001-95-8(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Precautionary statements

P262Do not get in eyes, on skin, or on clothing.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 60403
Product name: Potassium ionophore I
Purity: Selectophore
Packaging: 100mg
Price: $495
Updated: 2024/03/01

Sigma-Aldrich

Product number: 676377
Product name: Valinomycin
Purity: A cyclododecadepsi-peptide ionophore antibiotic.
Packaging: 25mg
Price: $117
Updated: 2022/05/15

Alfa Aesar

Product number: J62312
Product name: Valinomycin, 90+%
Packaging: 100mg
Price: $290
Updated: 2024/03/01

Alfa Aesar

Product number: J67410
Product name: Valinomycin, 10 mg/ml in DMSO
Purity: sterile-filtered
Packaging: 1ml
Price: $63.4
Updated: 2021/12/16

Cayman Chemical

Product number: 10009152
Product name: Valinomycin
Purity: ≥95%
Packaging: 5mg
Price: $25
Updated: 2024/03/01

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VALINOMYCIN Chemical Properties,Usage,Production

Description

Valinomycin (2001-95-8) is a selective K+ ionophore capable of transporting potassium ions through lipid membranes.1 Valinomycin can induce apoptosis in cells by causing a rapid loss of mitochondrial membrane potential via potassium efflux.2,3

Chemical Properties

white crystalline powder

Uses

antibiotic; LD50 (rat, po) 4 mg/kg

Uses

K+-selective ionophoric cyclodepsipeptide; potassium ionophore which uncouples oxidative phosphorylation, induces apoptosis in murine thymocytes, inhibits NGF-induced neuronal differentiation and anta gonizes ET-induced vasoconstriction. Used as insecticide, nematocide.

Uses

Valinomycin is a hydrophobic cyclodepsipeptide with potent antitumour activity. Valinomycin is a highly selective potassium ionophore and this action leads to a diverse range of profound cell membrane effects. More recently, valinomycin has found application as a biosensor to detect to detect potassium efflux.

Uses

Valinomycin is a hydrophobic cyclodepsipeptide with potent antitumor activity. Valinomycin is a highly selective potassium ionophore and this action leads to a diverse range of profound cell membrane effects. More recently, valinomycin has found application as a biosensor to detect to detect potassium efflux.

Uses

Insecticide, nematocide, Patterson, Wright, US 3520973 (1970 to Am. Cyanamid).

Definition

ChEBI: Valinomycin is a twelve-membered cyclodepsipeptide composed of three repeating D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains. It has a role as an antiviral agent, an antimicrobial agent, a potassium ionophore and a bacterial metabolite. It is a cyclodepsipeptide and a macrocycle.

General Description

Shiny crystalline solid. Used as an insecticide and nematocide. Not registered as a pesticide in the U.S.

Reactivity Profile

VALINOMYCIN is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Health Hazard

VALINOMYCIN is highly toxic orally.

Fire Hazard

When heated to decomposition, VALINOMYCIN emits toxic fumes of nitrogen oxides.

Biological Activity

Selective K + ionophore (K 0.5 values are 48, 73, 75, 93 and 246 mM for K + , Rb + , Cs + , Na + and Li + respectively) that transports K + across biological and artificial lipid membranes. Inhibits Ca 2+ -ATPase activity and induces apoptosis through mitochondrial membrane depolarization, caspase-3 activation and phosphatidylserine translocation in vitro .

Biochem/physiol Actions

Valinomycin affects the ion transport behavior of mitochondrial systems.

in vitro

valinomycin caused substantial cho cells death within 12 h of treatment. several apoptotic events were identified in valinomycin-treated cho cells, including caspase-3 activation, phosphatidylserine (ps) membrane translocation, and mitochondrial membrane depolarization during the first few hours of treatment. k+ efflux was reduced by elevating extracellular k+ concentrations [2].

in vivo

valinomycin is irritant in the case of eye and skin contact. inhalation of valinomycin can cause breathing disturbances and even loss of conscious. lethal doses (ld50) for mouse and rabbit is 2.5 mg/kg and 5 mg/kg respectively. valinomycin also shows to provoke lots of chronic effects, including damage of the central and peripheral nervous system, eyes, lens and cornea [1].

storage

Store at -20°C

Purification Methods

Recrystallise valinomycin from dibutyl ether or Et2O. It is dimorphic: modification A crystallises from n-octane, and modification B crystallises from EtOH/H2O. It is soluble in pet ether, CHCl3, AcOH, BuOAc and Me2CO. [Smith et al. J Am Chem Soc 97 7242 1975, UV, IR and NMR see Brocknmann & Schmidt-Kastner Chem Ber 88 57 1955, Beilstein 27 I 9728. 17 IV 9728.]

References

1) Pressman, (1976) Biological applications of ionophores; Annu. Rev. Biochem., 45 501 2) Furlong et al., (1998) Induction of apoptosis by valinomycin: mitochondrial permeability transition causes intracellular acidification; Cell Death Diff., 5 214 3) Inai et al. (1997) Valinomycin induces apoptosis of ascites hepatoma cells (AH-130) in relation to mitochondrial membrane potential; Cell Struc. Funct., 22 555

VALINOMYCIN Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from VALINOMYCIN manufacturers

Hebei Weibang Biotechnology Co., Ltd

Product: VALINOMYCIN 2001-95-8
Price: US $1.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10 mt
Release date: 2024-11-20

Zhejiang Zhulong Biotechnology Co.,Ltd

Product: valinomycin 2001-95-8
Price: US $0.00-0.00/g
Min. Order: 0.5g
Purity: 98.9 TLC; 95.8 HPLC
Supply Ability: 2kg
Release date: 2024-08-07

Hebei Mojin Biotechnology Co., Ltd

Product: VALINOMYCIN 2001-95-8
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-08-30

2001-95-8, VALINOMYCINRelated Search:

1,5-DIAMINO-3-OXAPENTANE N-SEC-BUTYL-N-PROPYLAMINE ISOVALERAMIDE Ethyl acetamidoacetate 1-AMINO-2-BUTANOL 2-Isopropoxy-ethylamine (R)-(-)-2-Amino-3-methyl-1-butanol D-2-Aminobutyric acid Propyl butyrate Isobutyl isovalerate Isobutyl butyrate (S)-(+)-1-METHOXY-2-PROPYLAMINE 2-HYDROXYACETAMIDE 2-N-FORMYLAMIONO-BUTYRICACID Isobutyl formate ISOPROPYL PROPIONATE 2-(ISOPROPYLAMINO)ETHANOL VALINOMYCIN

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,12,24,36-trimetyl-3,6,9,15,18,21,27,30,33-non

akis(1-methylethyl)-[qr]

Valinomycin, ≥98%(TLC),≥95%(HPLC),solid

Valinomycin, Streptomyces fulvissimus - CAS 2001-95-8 - Calbiochem

aleryl-d-valyl-l-lactoyl-l-valyl-d-alpha-hydroxyisovaleryl-d-valyl-l-lactoyl-l

antibioticn-329b

cyclic(d-alpha-hydroxyisovaleryl-d-valyl-l-lactoyl-l-valyl-d-alpha-hydroxyisov

nsc122023

nsc122023[qr]

valinomicin

valinomicin[qr]

Valinomycin, 97%, from Streptomyces fulvissimus

ValinoMycin, froM StreptoMyces fulvissiMus

-valyl)[qr]

VALINOMYCIN

VALINOMYCIN, STREPTOMYCES FULVISSIMUS

POTASSIUM IONOPHORE I

CYCLO[-L-VAL-D-HYLVA-D-VAL-L-LAC-]3

CYCLO(LAC-VAL-D-HIV-D-VAL-LAC-VAL-D-HIV-D-VAL-)

Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)3: HyIva = α-Hydroxyisovaleric acid, Lac = Lactic acid

VALINOMYCIN >94% PURITY

VALINOMYCIN READY MADE SOLUTION

VALINOMYCIN 99%

Valinomycin,90%

Valinomycin,96%

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)

VALINOMYCINRESEARCH GRADE

Potassium ionophore I,Valinomycin

Valinomycin,Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)3: HyIva = α-Hydroxyisovaleric acid, Lac = Lactic acid

1Cyclo(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)

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

VALINOMYCIN,CRYSTAL

VALINOMYCIN USP/EP/BP

Valinomycin (NSC-122023)

valamycin

(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-nonakis(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

2001-95-8

C54H90N6O18

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