VALINOMYCIN Chemical Properties

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)

Safety Information

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)

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

VALINOMYCIN Usage And Synthesis

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

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