Back to Search Start Over

Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors.

Authors :
Patrascu B
Mocanu S
Coman A
Madalan AM
Popescu C
Paun A
Matache M
Ionita P
Source :
International journal of molecular sciences [Int J Mol Sci] 2020 May 18; Vol. 21 (10). Date of Electronic Publication: 2020 May 18.
Publication Year :
2020

Abstract

Starting from dansyl-chloride, in reaction with 1,1-diphenylhydrazine and methoxyamine, two new fluorescent derivatives 1 and 2 were obtained and characterized by NMR, IR, UV-Vis, HR-MS, and fluorescence spectroscopy. The single-crystal X-ray structure was obtained for compound 2 . Both compounds generate free radicals by oxidation, as demonstrated by ESR spectroscopy. Compound 1 generates the corresponding hydrazyl-persistent free radical, evidenced directly by ESR spectroscopy, while compound 2 generates in the first instance the methoxyaminyl short-lived free radical, which decomposes rapidly with the formation of the methoxy radical, evidenced by the ESR spin-trapping technique. By oxidation of compounds 1 and 2 , their fluorescence is quenched.

Details

Language :
English
ISSN :
1422-0067
Volume :
21
Issue :
10
Database :
MEDLINE
Journal :
International journal of molecular sciences
Publication Type :
Academic Journal
Accession number :
32443620
Full Text :
https://doi.org/10.3390/ijms21103559