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V3639

Sigma-Aldrich

Valinomycin

Ready Made Solution, ~1 mg/mL in DMSO

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C54H90N6O18
CAS Number:
2001-95-8
Molecular Weight:
1111.32
Beilstein:
78657
MDL number:
MFCD00005114
UNSPSC Code:
51102829
PubChem Substance ID:
24900743
NACRES:
NA.76

biological source

Streptomyces sp.

Quality Level

200

Assay

≥90% (HPLC)

form

liquid

storage condition

(Keep container tightly closed in a dry and well-ventilated place. Hydroscopic.)

concentration

~1 mg/mL in DMSO

color

colorless

antibiotic activity spectrum

Gram-positive bacteria
parasites
viruses

Mode of action

cell membrane | interferes

shipped in

wet ice

storage temp.

2-8°C

SMILES string

CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC1=O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C

InChI

1S/C54H90N6O18/c1-22(2)34-49(67)73-31(19)43(61)55-38(26(9)10)53(71)77-41(29(15)16)47(65)59-36(24(5)6)51(69)75-33(21)45(63)57-39(27(11)12)54(72)78-42(30(17)18)48(66)60-35(23(3)4)50(68)74-32(20)44(62)56-37(25(7)8)52(70)76-40(28(13)14)46(64)58-34/h22-42H,1-21H3,(H,55,61)(H,56,62)(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t31-,32-,33-,34-,35+,36+,37-,38-,39-,40+,41+,42+/m0/s1

InChI key

FCFNRCROJUBPLU-RPUZOQEISA-N

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General description

Chemical structure: peptide

Application

Valinomycin is a cyclic dodecadepsipeptides with potassium ionophoric properties. It is used to study ion transport in biological systems. It is used to study its inhibitory effect on intact cells and the growth of bacteria and yeast. It is used to induce apoptosis.

Biochem/physiol Actions

K+-selective ionophoric cyclodepsipeptide; potassium ionophore which uncouples oxidative phosphorylation, induces apoptosis in murine thymocytes, inhibits NGF-induced neuronal differentiation and antagonizes ET-induced vasoconstriction.
Valinomycin is a K+-selective ionophoric cyclodepsipeptide. It is a potassium ionophore which uncouples oxidative phosphorylation, induces apoptosis in murine thymocytes, inhibits NGF-induced neuronal differentiation and antagonizes ET-induced vasoconstriction. It is reported to be insecticidal, nematicidal and antiviral.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Hygroscopic.

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

188.6 °F - closed cup

Flash Point(C)

87 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Marcel H Tempelaars et al.
Applied and environmental microbiology, 77(8), 2755-2762 (2011-03-02)
Cereulide and valinomycin are highly similar cyclic dodecadepsipeptides with potassium ionophoric properties. Cereulide, produced by members of the Bacillus cereus group, is known mostly as emetic toxin, and no ecological function has been assigned. A comparative analysis of the antimicrobial
Viktor K Jirsa et al.
Brain : a journal of neurology, 137(Pt 8), 2210-2230 (2014-06-13)
Seizures can occur spontaneously and in a recurrent manner, which defines epilepsy; or they can be induced in a normal brain under a variety of conditions in most neuronal networks and species from flies to humans. Such universality raises the
Ko-Shing Chang et al.
Biosensors & bioelectronics, 31(1), 137-143 (2011-11-01)
A silicon nanowire field-effect transistor (SiNW-FET) coated with a polyvinyl chloride (PVC) membrane containing valinomycin (VAL) was employed as a biosensor (referred to as VAL-PVC/SiNW-FET) to detect the K(+)-efflux from live chromaffin cells. The detection sensitivity of K(+) with the
Kahori Shiba-Fukushima et al.
The Journal of biological chemistry, 289(48), 33131-33136 (2014-10-23)
PINK1/Parkin-mediated mitophagy is thought to ensure mitochondrial quality control in neurons as well as other cells. Upon the loss of mitochondrial membrane potential (ΔΨm), Lys-63-linked polyubiquitin chains accumulate on the mitochondrial outer membrane in a Parkin-dependent manner. However, the physiological
TianHua Zhang et al.
Biochimica et biophysica acta, 1838(10), 2425-2430 (2014-05-27)
Daptomycin is a lipopeptide antibiotic that is used clinically to treat severe infections caused by Gram-positive bacteria. Its bactericidal action involves the calcium-dependent binding to membranes containing phosphatidylglycerol, followed by the formation of membrane-associated oligomers. Bacterial cells exposed to daptomycin
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