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Conjugation of Bioactive Molecules to a Fluorescent Dithiomaleimide by Photoinduced and BEt 3 ‐Initiated Thio‐Click Reactions
Author(s) -
Lázár László,
Nagy Miklós,
Borbás Anikó,
Herczegh Pál,
Zsuga Miklós,
Kéki Sándor
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501116
Subject(s) - chemistry , maleimide , fluorescence , alkene , photochemistry , ether , thio , derivative (finance) , tetrahydrofuran , click chemistry , thiol , polymer chemistry , organic chemistry , physics , quantum mechanics , solvent , financial economics , economics , catalysis
Abstract Two versions of the free‐radical thiol–ene addition, a photoinduced reaction in the presence of 2,2‐dimethoxy‐2‐phenylacetophenone, and a UV‐light‐free hydrothiolation using triethylborane as the initiator, were studied for the conjugation of fluorescent dithiomaleimide to biologically active compounds. A dithiomaleimide derivative bearing a vinyl ether functionality was prepared as the alkene partner. This was coupled with a range of thiols, including thiosugars, captopril, N ‐acetyl‐ L ‐cysteine, and sodium 2‐sulfonatoethanethiol. The Et 3 B‐initiated method was superior to the photoinduced reaction, as it minimized decomposition of the sensitive maleimide group. The vinyl ether derivative and the addition products showed green light emission in tetrahydrofuran. The compounds all showed almost identical absorption and emission spectra, proving that the structure of the thiols has no influence on the fluorescence properties of the maleimide part of the molecules. The hydrothiolation products showed relatively high quantum yields.