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Merck
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SML2379

Sigma-Aldrich

Fluorizoline

≥98% (HPLC)

Sinónimos:

2,5-bis(4-Chlorophenyl)-4,4,5-trifluoro-4,5-dihydrothiazole, 4,4,5-Trifluoro-2,5-bis(4-chlorophenyl)-4,5-dihydrothiazole

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About This Item

Fórmula empírica (notación de Hill):
C15H8Cl2F3NS
Número de CAS:
1362243-70-6
Peso molecular:
362.20
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

ClC(C=C1)=CC=C1C2=NC(F)(F)C(C3=CC=C(Cl)C=C3)(F)S2

Biochem/physiol Actions

Fluorizoline is a prohibitin (PHB) 1/2-binding diaryl trifluorothiazoline compound that induces p53-independent apoptosis in various cancer cultures (IC50 from 1.6 μM/Bx-PC3 to 9.4 μM/JeKo 1; 24 h) and upregulates proapoptotic Noxa and Bim mRNAs in wild-type, but not PHBs-depleted MEFs. Box(-/-)/Bak(-/-) or Noxa(-/-)/Bim(-/-) MEFs as well as BAX/BAK- or NOXA-downregulated HeLa cells are resistant to fluorizoline-induced apoptosis. Fluorizoline treatment is shown to prevent active RAS-CRAF interaction and downstream MEK1/2 activation following EGF stimulation in HeLa cells (10 μM).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Alba Pérez-Perarnau et al.
Angewandte Chemie (International ed. in English), 53(38), 10150-10154 (2014-09-10)
A new class of small molecules, with an unprecedented trifluorothiazoline scaffold, were synthesized and their pro-apoptotic activity was evaluated. With an EC50 in the low micromolar range, these compounds proved to be potent inducers of apoptosis in a broad spectrum
The prohibitin-binding compound fluorizoline induces apoptosis in chronic lymphocytic leukemia cells ex vivo but fails to prevent leukemia development in a murine model.
Marina Wierz et al.
Haematologica, 103(4), e154-e157 (2018-01-07)
H Yurugi et al.
Oncogene, 36(33), 4778-4789 (2017-04-18)
KRAS is one of the most frequently mutated oncogenes in human non-small cell lung cancers (NSCLCs). RAS proteins trigger multiple effector signalling pathways including the highly conserved RAF-MAPK pathway. CRAF, a direct RAS effector protein, is required for KRAS-mediated tumourigenesis.
Ana M Cosialls et al.
Haematologica, 102(9), 1587-1593 (2017-06-18)
Fluorizoline is a new synthetic molecule that induces apoptosis by selectively targeting prohibitins. In the study herein, the pro-apoptotic effect of fluorizoline was assessed in 34 primary samples from patients with chronic lymphocytic leukemia. Fluorizoline induced apoptosis in chronic lymphocytic
Helena Pomares et al.
Oncotarget, 7(40), 64987-65000 (2016-08-20)
Fluorizoline is a new synthetic molecule that induces apoptosis by selectively targeting prohibitins (PHBs). In this study, the pro-apoptotic effect of fluorizoline was assessed in two cell lines and 21 primary samples from patients with debut of acute myeloid leukemia
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