ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Spiropyran 5,6′-dichloro-1,3,3-trimethylspiro[indoline-2,2′-2H-pyrano[3,2-h]quinoline] application as a spectorphotometric and fluorescent probe for glutathione and cysteine sensing

A. A. Shcherbatykh, M. S. Chernov’yants, N. A. Voloshin, and A. V. Chernyshev

Department of Chemistry, Southern Federal University, Rostov-on-Don, Russia

E-mail: chernov@sfedu.ru

Received: 16 November 2021  Accepted: 1 May 2022

Abstract:

Sulfur-containing amino acids play an essential role in the physiological process. Spiropyrans are a class of photochromic substances, which can be used for the determination of sulfur-containing amino acids and oligopeptides, such as cysteine, methionine, glutathione. Herein we used spiropyran 5,6′-dichloro-1,3,3-trimethylspiro[indoline-2,2′-2H-pyrano[3,2-h]quinoline] (DTIQ) for analytes sensing. DTIQ demonstrates a selective response toward glutathione in the presence of cysteine and methionine. It allows us to develop simple, rapid and sensible methods of spectrophotometric and fluorimetric glutathione assay. The developed methods were applied to quantification of glutathione in the dietary supplement and human urine. At the same time, DTIQ was found to bind Cu²⁺ with the formation of complex, which can be destroyed by glutathione or cysteine. Since that is accompanied by absorption changes, DTIQ application as a glutathione and cysteine “ON–OFF-ON” sensor is possible. The elaborated methods are characterized by low limits of detection, which are quite enough to quantify analytes at the level of their physiological concentration.

Keywords: Cysteine; Glutathione; Spiropyrans; Spectrophotometry; Fluorimetry

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02259-0

Chemical Papers 76 (9) 5541–5550 (2022)