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ChemicalBook--->CAS DataBase List--->36098-33-6

36098-33-6

36098-33-6 Structure

36098-33-6 Structure
IdentificationBack Directory
[Name]

F16
[CAS]

36098-33-6
[Synonyms]

F16
F16 (F-16
Compound F16)
F-16;COMPOUND F16
F16/Cell proliferation inhibitor (F16)
4-[(E)-2-(INDOL-3-YL)ETHENYL]-N-METHYLPYRIDINIUM IODIDE
3-[2-(1-methylpyridin-1-ium-4-yl)ethenyl]-1H-indole,iodide
4-[(1E)-2-(1H-INDOL-3-YL)ETHENYL]-1-METHYL-PYRIDINIUM IODIDE
[Molecular Formula]

C16H15IN2
[MDL Number]

MFCD00050298
[MOL File]

36098-33-6.mol
[Molecular Weight]

362.21
Chemical PropertiesBack Directory
[storage temp. ]

Store at -20°C
[solubility ]

≤500μg/ml in ethanol;20mg/ml in DMSO;25mg/ml in dimethyl formamide
[form ]

Orange solid.
[color ]

Yellow to orange
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H319-H335-H315
[Precautionary statements ]

P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Hazard InformationBack Directory
[Uses]

F16 is a cell-permeable mitochondrial toxin with apoptotic and necrotic action in tumor cell lines.
[Biological Activity]

f16 is a small, cationic, lipophilic, and fluorescent molecule capable of binding preferentially to mitochondrial membranes and disrupts their function. f16 is a potential antitumor agent.f16 affected growth in some mouse and human breast cancer cell lines. f16 resulted in a dramatic decrease in the number of cells in s phase and an increase in the percentage of cells in g1 phase [1]. prolonged incubation with 3 μm f16 led to increased cell death of f16-sensitive cells but not of f16-resistant ones. f16 accumulation in mitochondria induced mitochondrial damage characterized by imbalance of volumetric homeostasis, failure to synthesize atp, cytochrome c release and increased production of reactive oxy gen species [1]. f16 incubation decreased the cellular atp pool in both parental eph4-a6 and bcl-2-overexpressing eph4-a6.c13 and eph4-a6.c18 cells in a time-dependent manner [1]. treatment with f16 promoted early release of cytochrome c in transformed eph4-a6 cells. treatment with f16 (0.3-3 μm) resulted in the characteristic apoptotic dna laddering in the eph4-a6 cells. f16-induced mitochondrial dysfunction triggers apoptosis or necrosis. f16 induced necrosis in various cell lines resistant to apoptosis [2].
[References]

[1] fantin v r, berardi m j, scorrano l, et al. a novel mitochondriotoxic small molecule that selectively inhibits tumor cell growth[j]. cancer cell, 2002, 2(1): 29-42.
[2] fantin v r, leder p. f16, a mitochondriotoxic compound, triggers apoptosis or necrosis depending on the genetic background of the target carcinoma cell[j]. cancer research, 2004, 64(1): 329-336.
Spectrum DetailBack Directory
[Spectrum Detail]

F16(36098-33-6)1HNMR
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100-43-6

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