CAS 28380-24-7

Nigericin

Description:

Nigericin is a polyether antibiotic produced by the fermentation of certain species of Streptomyces, particularly Streptomyces hygroscopicus. It is characterized by its ability to transport potassium ions across biological membranes, which disrupts cellular ion homeostasis. This ionophore exhibits a unique structure that includes a macrocyclic ring, allowing it to form complexes with cations, particularly K+ and Na+. Nigericin is known for its antimicrobial properties and has been studied for its potential applications in research and medicine, particularly in the context of cell biology and pharmacology. It can influence various cellular processes, including mitochondrial function and apoptosis, by altering ion gradients. Additionally, nigericin has been utilized in studies involving ion transport mechanisms and cellular signaling pathways. However, its use is often limited due to potential toxicity and the need for careful handling in laboratory settings. Overall, nigericin serves as a valuable tool in biochemical research, providing insights into ion transport and cellular dynamics.

Formula: C₄₀H₆₈O₁₁

InChI: InChI=1S/C40H68O11/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34/h21-35,41,44H,11-20H2,1-10H3,(H,42,43)/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+/m0/s1

InChI key: InChIKey=DANUORFCFTYTSZ-SJSJOXFOSA-N

SMILES: C[C@H]1[C@]2(O[C@@](C)(C1)[C@@]3(O[C@@](C)(CC3)[C@@]4(O[C@](C[C@@H]4C)([C@]5(O[C@](CO)(O)[C@H](C)C[C@@H]5C)[H])[H])[H])[H])O[C@H](C[C@@H]6O[C@@]([C@H](C(O)=O)C)([C@@H](C)CC6)[H])C[C@@H](OC)[C@H]2C

Synonyms:

• (2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10R)-2-{(2S,2'R,3'S,5R,5'R)-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl]-2,3'-dimethyloctahydro-2,2'-bifuran-5-yl}-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]dec-7-yl]methyl}-3-methyltetrahydro-2H-pyran-2-yl]propanoic acid
• (2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10S)-2-{(2S,2'R,3'S,5R,5'R)-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl]-2,3'-dimethyloctahydro-2,2'-bifuran-5-yl}-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]dec-7-yl]methyl}-3-methyltetrahydro-2H-pyran-2-yl]propanoic acid
• 1,6-Dioxaspiro[4.5]decane, nigericin deriv.
• Antibiotic K 178
• Antibiotic M 2
• Antibiotic X 464
• Azalomycin M
• Helixin C
• Nigericin
• Nigericin Sodium From Streptomyces*Hygroscopicus
• Polyetherin A
• Stereoisomer of tetrahydro-6-[[9-methoxy-2,4,10-trimethyl-2-[octahydro-2,3′-dimethyl-5′-[tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl][2,2′-bifuran]-5-yl]-1,6-dioxaspiro[4.5]dec-7-yl]methyl]-α,3-dimethyl-2H-pyran-2-acetic acid
• X 464

Nigericin

CAS: 28380-24-7

Nigericin isantimicrobial, antimalarial, anticoronaviral and anticancer, promoting cellular potassium efflux, pyroptosis and apoptosis through Wnt/β-catenin.

Formula: C₄₀H₆₈O₁₁

Purity: 98.50%

Color and Shape: White Solid

Molecular weight: 724.96

Ref: TM-T16323

NIGERICIN SODIUM SALT

CAS: 28380-24-7

Formula: C₄₀H₆₈O₁₁

Purity: 97%

Color and Shape: Solid

Molecular weight: 724.9613

Ref: IN-DA00BCHJ

Nigericin

CAS: 28380-24-7

Formula: C₄₀H₆₈O₁₁

Color and Shape: White To Off-White Solid

Molecular weight: 724.98

Ref: 4Z-N-351

Nigericin

CAS: 28380-24-7

Nigericin

Molecular weight: 724.97g/mol

Ref: 54-BITP3218

Nigericin

CAS: 28380-24-7

Nigericin is a drug that belongs to the class of pharmacological agents. It has been shown to be effective in the treatment of solid tumours. Nigericin is an amphiphilic molecule that can enter cells through passive diffusion and interacts with the mitochondrial membrane potential, leading to cell lysis. Nigericin also interacts with the cell-surface receptor toll-like receptor 4, which initiates signal pathways that lead to cell death. This drug is active against gram-positive bacteria but not against gram-negative bacteria such as Escherichia coli or Pseudomonas aeruginosa. Nigericin has shown high activity in killing cancer cells and is used for the treatment of patients with solid tumours at physiological levels, typically around 100 μM (1 mM). It has been found that nigericin may act synergistically with dimethyl fumarate, a drug used for treating multiple sclerosis, under acidic conditions.

Formula: C₄₀H₆₈O₁₁

Purity: Min. 95%

Molecular weight: 724.96 g/mol

Ref: 3D-DBA38024