Syntheses of some p-nitrophenyl substituted tetrazolium salts as electron acceptors for the demonstration of dehydrogenases

Kwan Chung Tsou, Chao Shing Cheng, Marvin M. Nachlas, Arnold M. Seligman

Research output: Contribution to journalArticle

Abstract

A number of p-nitrophenyl substituted tetrazolium salts have been synthesized for the histochemical demonstration of de, hydrogenase in tissues. One of these, 2,2′-di-p-nitrophenyl-5,5′-diphenyl-3,3′-(3,3′- dimethoxy-4,4′-biphenylene)-ditetrazolium chloride (XA, "nitro-BT") (Table IV) was found to be superior to any tetrazole so far developed for histochemistry-and makes possible the demonstration of the dehydrogenases at the cytological level. It was also found that during the coupling of a tetrazotized biphenylenediamine with a phenylhydrazone, one of the diazonium groups could be replaced by hydrogen to form a phenyl group. Thus, in the formation of the above-mentioned ditetrazolium salt, a monotetrazolium salt, 2-p-nitrophenyl-5-phenyl-3-(3,3′-dimethoxy-4-biphenylyl)-tetrazolium chloride (IIIA) (Table III), was obtained concomitantly. The isolation of the mono- and diformazans is described and mechanisms for the formation of the monoformazans are discussed. The nature of the monotetrazole that is found as a contaminant in commercial preparations of ditetrazoles is thus ellucidated.

Original languageEnglish (US)
Pages (from-to)6139-6144
Number of pages6
JournalJournal of the American Chemical Society
Volume78
Issue number23
StatePublished - 1956
Externally publishedYes

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Tetrazolium Salts
Chlorides
Oxidoreductases
Demonstrations
Salts
Electrons
Nitroblue Tetrazolium
Hydrogenase
Hydrogen
Impurities
Tissue
diformazan dye
1H-tetrazole
diphenyl
phenylhydrazone
1,21-diamino-4,9,13,18-tetraazahenicosane

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Syntheses of some p-nitrophenyl substituted tetrazolium salts as electron acceptors for the demonstration of dehydrogenases. / Tsou, Kwan Chung; Cheng, Chao Shing; Nachlas, Marvin M.; Seligman, Arnold M.

In: Journal of the American Chemical Society, Vol. 78, No. 23, 1956, p. 6139-6144.

Research output: Contribution to journalArticle

Tsou, Kwan Chung ; Cheng, Chao Shing ; Nachlas, Marvin M. ; Seligman, Arnold M. / Syntheses of some p-nitrophenyl substituted tetrazolium salts as electron acceptors for the demonstration of dehydrogenases. In: Journal of the American Chemical Society. 1956 ; Vol. 78, No. 23. pp. 6139-6144.
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AB - A number of p-nitrophenyl substituted tetrazolium salts have been synthesized for the histochemical demonstration of de, hydrogenase in tissues. One of these, 2,2′-di-p-nitrophenyl-5,5′-diphenyl-3,3′-(3,3′- dimethoxy-4,4′-biphenylene)-ditetrazolium chloride (XA, "nitro-BT") (Table IV) was found to be superior to any tetrazole so far developed for histochemistry-and makes possible the demonstration of the dehydrogenases at the cytological level. It was also found that during the coupling of a tetrazotized biphenylenediamine with a phenylhydrazone, one of the diazonium groups could be replaced by hydrogen to form a phenyl group. Thus, in the formation of the above-mentioned ditetrazolium salt, a monotetrazolium salt, 2-p-nitrophenyl-5-phenyl-3-(3,3′-dimethoxy-4-biphenylyl)-tetrazolium chloride (IIIA) (Table III), was obtained concomitantly. The isolation of the mono- and diformazans is described and mechanisms for the formation of the monoformazans are discussed. The nature of the monotetrazole that is found as a contaminant in commercial preparations of ditetrazoles is thus ellucidated.

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