Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines

Abstract

Functional organic dyes play a key role in many fields, namely in biotechnology and medical diagnosis. Herein, we report two novel 2,3- and 3,4-dihydroxyphenyl substituted rosamines (3 and 4, respectively) that were successfully synthesized through a microwave-assisted protocol. The best reaction yields were obtained for rosamine 4, which also showed the most interesting photophysical properties, specially toward biogenic amines (BAs). Several amines including n- and t-butylamine, cadaverine, and putrescine cause spectral changes of 4, in UV–Vis and fluorescence spectra, which are indicative of their potential application as an effective tool to detect amines in acetonitrile solutions. In the gas phase, the probe response is more expressive for spermine and putrescine. Additionally, we found that methanolic solutions of rosamine 4 and n-butylamine undergo a pink to yellow color change over time, which has been attributed to the formation of a new compound. The latter was isolated and identified as 5 (9−aminopyronin), whose solutions exhibit a remarkable increase in fluorescence intensity together with a shift toward more energetic wavelengths. Other 9-aminopyronins 6a, 6b, 7a, and 7b were obtained from methanolic solutions of 4 with putrescine and cadaverine, demonstrating the potential of this new xanthene entity to react with primary amines.

Biogenic Amine Sensing Based on Rosamine a N-Methylpyridinium Derivative Supported on Silica Materials from Rice Husk

“…In a previous but using other rosamine analogue, the same preference for the studied amines was observed: n-butylamine > cadaverine > putrescine [29]. The sensitivity of Ros4PyMe@SBA to the tested amines can be related not only with their nucleophilicity, that follows the order: aniline < cadaverine < n-butylamine = putrescine [30], but also with the preference for the presence of two amino groups in the amine structure which explains the fact that the sensor responds better to putrescine than n-butylamine.…”

UV-Vis spectroscopic investigation on color change kinetics of lac dye as influenced by some food spoilage metabolites: validation for milk quality monitoring

“…However, addition of higher amount (80 and 90 µL) of tyramine resulted in faster and deeper color change compared to 60 and 70 µL. Change in the color of the dye solution after addition of tyramine is due to the increase in the pH of dye solution by reaction with tyramine, which led to deprotonation of dye molecules (Monteiro-Silva et al , 2021; Rukchon et al , 2014). Deprotonation of the dye molecule led to an increase in the absorption of the dye solution at 528 nm and reduction in absorption at 488 nm (Figure A4 Supporting file).…”

Novel pH-sensitive catechol dyes synthesised by a three component one-pot reaction

“…Proof of that is the increasing number of publications on this subject, covering various disciplines such as organic chemistry ( Yang et al, 2002 ; Iacomino et al, 2017 ; Ji et al, 2019 ; Mancebo-Aracil et al, 2019 ; Nador et al, 2021 ), surface and supramolecular chemistry ( Panchireddy et al, 2018 ; Qiu et al, 2018 ; Lyu et al, 2019 ; Souza Campelo et al, 2020 ), or electrochemistry ( Golabi, Nematollahi, 1997 ; Shahrokhian, Hamzehloei, 2003 ; Zhao et al, 2012 ; Toghan et al, 2019 ). With regard to the use of catechols in optical applications, several examples have been reported where catechol is attached to a fluorescent compound, taking advantage of the synergy between the chelating properties of catechol and the optical properties of the fluorophore to generate new chemosensors ( Evangelio et al, 2008 ; An et al, 2010a ; Queirós et al, 2012 ; Queirós et al, 2014 ; Yin et al, 2014 ; Queirós et al, 2015 ; Monteiro-Silva et al, 2021 ), and materials ( Kaushik et al, 2015 ; Nador et al, 2018a ; Nador et al, 2018b ; Mancebo-Aracil et al, 2019 ). Catechols have also been used as pendant groups in fluorescent polymers to improve their adhesion ( Zhang et al, 2016 ; Gapin et al, 2020 ; Zhan et al, 2021 ).…”