formazan

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/07/08 15:24:50」(JST)

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Reduction of a tetrazolium to a formazan. The "Rs" stand-in for various organic groups that define the various tetrazolium salts and provide their unique chemical characteristics.

Formazan dyes are artificial chromogenic products of the reduction of tetrazolium salts by dehydrogenases and reductases. They have a variety of colors from dark blue to deep red to orange, depending on the original tetrazolium salt used as the substrate for the reaction.

Leading examples of tetrazolium salts include:^[1]

INT or 2-(4-iodophenyl)-3-(4-nitrophenyl)-5-phenyl-2H-tetrazolium chloride, which is water insoluble.
MTT or 3-(4,5-dimethyl-2-thiazolyl)-2, 5-diphenyl-2H-tetrazolium bromide, which is water insoluble and used in the MTT assay.
XTT or 2,3-bis-(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide, which is water soluble.
MTS or 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium, which is water soluble and used in the MTS assay.
TTC or tetrazolium chloride or 2,3,5-triphenyl-2H-tetrazolium chloride, which is water soluble.
NBT used in a diagnostic test, particularly for chronic granulomatous disease and other diseases of phagocyte function.

When reduced in a cell, either enzymatically or through direct reaction with NADH or NADPH, the classical tetrazolium salt, MTT, turns blue to purple and may form an insoluble precipitate. These formazan dyes are commonly used in cell proliferation and toxicity assays like the EpiDerm^[2] and EpiSkin tests since they only stain living, metabolically active cells.^[3]^[4]

References

^ Altman FP (1976). "Tetrazolium salts and formazans". Prog. Histochem. Cytochem. 9 (3): 1–56. PMID 792958.
^ http://www.mattek.com Missing or empty |title= (help)
^ Marshall NJ, Goodwin CJ, Holt SJ (June 1995). "A critical assessment of the use of microculture tetrazolium assays to measure cell growth and function". Growth Regul. 5 (2): 69–84. PMID 7627094.
^ Scudiero DA, Shoemaker RH, Paull KD, et al. (1 September 1988). "Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines". Cancer Res. 48 (17): 4827–33. PMID 3409223.

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1. 好中球減少症および好中球機能不全の検査での評価 laboratory evaluation of neutropenia and neutrophil dysfunction
2. 慢性肉芽腫性疾患：病因、臨床症状、および診断 chronic granulomatous disease pathogenesis clinical manifestations and diagnosis

English Journal

Mechanical and structural response of a hybrid hydrogel based on chitosan and poly(vinyl alcohol) cross-linked with epichlorohydrin for potential use in tissue engineering.

Garnica-Palafox IM, Sánchez-Arévalo FM, Velasquillo C, García-Carvajal ZY, García-López J, Ortega-Sánchez C, Ibarra C, Luna-Bárcenas G, Solís-Arrieta L.Sourcea Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México , Apdo. Postal 70-360, Cd. Universitaria , México D.F. , 04360 , México.
Journal of biomaterials science. Polymer edition.J Biomater Sci Polym Ed.2013 Sep 5. [Epub ahead of print]
The development and characterization of a hybrid hydrogel based on chitosan (CS) and poly(vinyl alcohol) (PVA) chemically cross-linked with epichlorohydrin (ECH) is presented. The mechanical response of these hydrogels was evaluated by uniaxial tensile tests; in addition, their structural properties
PMID 24007370

Highly Efficient Visual Detection of Trace Copper(II) and Protein by the Quantum Photoelectric Effect.

Wang P, Lei J, Su M, Liu Y, Hao Q, Ju H.SourceState Key Laboratory of Analytical Chemistry for Life Science, Department of Chemistry, Nanjing University , Nanjing 210093, China.
Analytical chemistry.Anal Chem.2013 Sep 3. [Epub ahead of print]
This work presented a photocurrent response mechanism of quantum dots (QDs) under illumination with the concept of a quantum photoelectric effect. Upon irradiation, the photoelectron could directly escape from QDs. By using nitro blue tetrazolium (NBT) to capture the photoelectron, a new visual syst
PMID 23964566

Superoxide generated by pyrogallol reduces highly water-soluble tetrazolium salt to produce a soluble formazan: A simple assay for measuring superoxide anion radical scavenging activities of biological and abiological samples.

Xu C, Liu S, Liu Z, Song F, Liu S.SourceChangchun Center of Mass Spectrometry & Chemical Biology Laboratory, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, PR China; University of the Chinese Academy of Sciences, Beijing 100039, PR China.
Analytica chimica acta.Anal Chim Acta.2013 Sep 2;793:53-60. doi: 10.1016/j.aca.2013.07.027. Epub 2013 Jul 15.
Superoxide anion radical (O2(-)) plays an important role in several human diseases. The xanthine/xanthine oxidase system is frequently utilized to produce O2(-). However, false positive results are easily got by using this system. The common spectrophotometric probes for O2(-) are nitroblue tetrazol
PMID 23953206

Japanese Journal

BF₃-Functionalized Silica-Coated Magnetic Nanoparticles as a Novel Heterogeneous Solid Acid for Synthesis of Formazan Derivatives via a Green Protocol

Bamoniri Abdolhamid,Moshtael-Arani Naimeh
Bulletin of the Chemical Society of Japan 88(5), 662-672, 2015-05
NAID 40020459996

BF3-Functionalized Silica-Coated Magnetic Nanoparticles as a Novel Heterogeneous Solid Acid for Synthesis of Formazan Derivatives via a Green Protocol

Bamoniri Abdolhamid,Moshtael-Arani Naimeh
Bulletin of the Chemical Society of Japan 88(5), 662-672, 2015
… The activity of this super solid acid was probed through the synthesis of aryl diazonium salts as the starting reactant and then, their diazo coupling with aldehyde phenylhydrazones for formation of formazan derivatives in a solvent-free medium at room temperature. …
NAID 130005069515

BF3-Functionalized Silica-Coated Magnetic Nanoparticles as a Novel Heterogeneous Solid Acid for Synthesis of Formazan Derivatives via a Green Protocol

Bamoniri Abdolhamid,Moshtael-Arani Naimeh
Bulletin of the Chemical Society of Japan advpub(0), 2015
… The activity of this super solid acid was probed through the synthesis of aryl diazonium salts as the starting reactant and then, their diazo coupling with aldehyde phenylhydrazones for formation of formazan derivatives in a solvent-free medium at room temperature. …
NAID 130004801866

Related Pictures

[1] Altman FP (1976). "Tetrazolium salts and formazans". Prog. Histochem. Cytochem. 9 (3): 1–56. PMID 792958.

[2] ttp://www.mattek.com Missing or empty |title= (help)

[3] Marshall NJ, Goodwin CJ, Holt SJ (June 1995). "A critical assessment of the use of microculture tetrazolium assays to measure cell growth and function". Growth Regul. 5 (2): 69–84. PMID 7627094.

[4] Scudiero DA, Shoemaker RH, Paull KD, et al. (1 September 1988). "Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines". Cancer Res. 48 (17): 4827–33. PMID 3409223.

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