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SML1793

Sigma-Aldrich

MI-4F

≥98% (HPLC)

Synonym(s):

2-[2-(4-Fluorophenyl)ethenyl]-3-phenyl-5-(phenylamino)-1,3,4-thiadiazolium chloride, M1 4F

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About This Item

Empirical Formula (Hill Notation):
C22H17ClFN3S
CAS Number:
346460-45-5
Molecular Weight:
409.91
UNSPSC Code:
12352202
PubChem Substance ID:
329826068

assay

≥98% (HPLC)

form

powder

color

, light yellow to yellow-orange

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

FC(C=C1)=CC=C1C=CC2=[N+](C3=CC=CC=C3)N=C(NC4=CC=CC=C4)S2.[Cl-]

Biochem/physiol Actions

MI-4F is mesoionic compound that exhibits potent anticancer activity against multiple cancer cell lines and in vivo.
MI-4F is mesoionic compound that exhibits potent anticancer activity against multiple cancer cell lines and in vivo. MI-4F induces apoptosis in HepG2 cells. MI-4F appears to inhibit calcium efflux through inhibition formation of mitochondrial permeability transition pore (MPTP). MI-4F inhibits superoxide dismutase. MI-4F is not susceptible to MDR transporters P-glycoprotein, ABCG2 and MRP1. MI-4F also inhibits ABCG2-mediated efflux of mitoxantrone.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
106M4618V

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Amanda do Rocio Andrade Pires et al.
Chemico-biological interactions, 186(1), 1-8 (2010-04-14)
The main goal of this work was to investigate the relationship between the effects of three new 1,3,4-thiadiazolium mesoionic derivatives on mitochondrial bioenergetics and their previously described chemical structure and antimelanoma activity. The 4-phenyl-5-(2'-Y, 4'-X or 4'-X-cinnamoyl)-1,3,4-thiadiazolium-2-phenylamine chlorides differed from
Gustavo Jabor Gozzi et al.
PloS one, 10(6), e0130046-e0130046 (2015-06-18)
In this work, we evaluated the cytotoxicity of mesoionic 4-phenyl-5-(2-Y, 4-X or 4-X-cinnamoyl)-1,3,4-thiadiazolium-2-phenylamine chloride derivatives (MI-J: X=OH, Y=H; MI-D: X=NO2, Y=H; MI-4F: X=F, Y=H; MI-2,4diF: X=Y=F) on human hepatocellular carcinoma (HepG2), and non-tumor cells (rat hepatocytes) for comparison. MI-J, M-4F
Amanda do Rocio Andrade Pires et al.
European journal of pharmacology, 770, 78-84 (2015-12-17)
Mesoionic compounds have shown antitumor and citotoxic activity against different tumor cells lines, which has been attributed to their physical and chemical characteristics. Among these compounds, the 1,3,4-thiadiazolium-2-phenylamine derivatives have been highlighted due to their important anti-melanoma activity. In this

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