Valinomycin

SIGMA/V0627 - ≥98% (TLC), ≥90% (HPLC)

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

CAS Number: 2001-95-8
Empirical Formula (Hill Notation): C₅₄H₉₀N₆O₁₈
Molecular Weight: 1111.32
EC Number: 217-896-6
MDL Number: MFCD00005114
Linear Formula: C₅₄H₉₀N₆O₁₈
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-V0627-10MG	10 mg	$107.00 1/EA	Add To Favorites
45-V0627-25MG	25 mg	$167.00 1/EA	Add To Favorites
45-V0627-100MG	100 mg	$414.00 1/EA	Add To Favorites
45-V0627-500MG	500 mg	$2100.00 1/EA	Add To Favorites

Valinomycin is a cyclododecadepsi-peptide ionophore antibiotic. It is a potassium ionophore that transports K+ across biological and artificial lipid membranes. Valinomycin can induce K+ conductivity in cell membranes, uncouples oxidative phosphorylation and induces apoptosis.

Properties
Descriptions
Safety Info.
Basic Data

antibiotic activity spectrum	Gram-positive bacteria
	parasites
	viruses
assay	≥90% (HPLC)
	≥98% (TLC)
color	white
form	powder
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
mode of action	cell membrane \| interferes
Quality Level	300
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
solubility	DMSO: ≥50 mg/mL
	H₂O: insoluble
storage condition	(Keep container tightly closed in a dry and well-ventilated place.)
storage temp.	2-8°C

Application:	Valinomycin has been used: • to equilibrate intracellular pH and extracellular pH of 5 (and 6-)-carboxyfluorescein succinimidyl ester (cFSE) in Escherichia coli strain B23 • as an ionophore to equilibrate intracellular pH and extracellular pH of lactic acid bacteria (LAB) strains • to establish the desired pH for acid-base transition and formation of K⁺-valinomycin diffusion potential
Biochem/physiol Actions:	K⁺-selective ionophore which uncouples oxidative phosphorylation.
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.
Biochem/physiol Actions:	Valinomycin selectively transfers alkali metal ions via biological and synthetic membranes. The formation of a metal ion-peptide complex contributes to this ion-transporting. Valinomycin can create stable complexes with potassium, rubidium, and cesium (K⁺, Rb⁺, and Cs⁺) .
General description:	Chemical structure: peptide
General description:	Valinomycin is a cyclic peptide, which contains d-valine, d-α-hydroxyvaleric acid, l-valine, and l-lactic acid in the sequential order of cyclo-[(l-Val-d-Hyv-d-Val-l-Lac)₃].
General description:	Valinomycin, a nonribosomal peptide (NRP), is proposed to have a structure of a 24-membered cyclic peptide cyclo-(d-α-hydroxyisovaleryl-d-valyl-l-lactyl-l-valyl)2. It exhibits antitumor properties and plays a major role as a mitophagy activator. Initially isolated as an antibiotic compound, valinomycin has demonstrated antibacterial activity against Mycobacterium tuberculosis. Moreover, it has been identified as a potent antiviral agent against a wide spectrum of viruses, including human coronavirus, bunyavirus, enterovirus, and flavivirus.
Other Notes:	Keep container tightly closed in a dry and well-ventilated place.
Packaging:	10MG,25MG,100MG,500MG

Symbol	GHS06
Signal word	Danger
Hazard statements	H300 + H310
Precautionary statements	P262 - P280 - P301 + P310 + P330 - P302 + P352 + P310
Hazard Codes	T+
Risk Statements	27/28
Safety Statements	28-36/37-45
RIDADR	UN 2811 6.1 / PGI
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥90% (HPLC); ≥98% (TLC)
Storage Temp.	2-8°C
UNSPSC	12352200

To Order From a Quote