Work

Regio- and diastereoselective synthesis of cyclobutylated phenothiazines via [2 + 2] photocycloaddition: demonstrating wavelength-gated cycloreversion inside live cells

Year: 2024

Type: article

Abstract: a 'photoinduced-electron-transfer' (PET) mechanism, which is well corroborated with the experimental observations, Rehm-Weller equation, and computation studies. Delightfully, a wavelength-gated reversibility of the [2 + 2]-photocycloaddition reaction has been accomplished on the synthesized cyclobutylated phenothiazines. By monitoring the rate of the cycloreversion reactions for different derivatives, a structure-activity relationship has also been achieved. Interestingly, this phenomenon was further replicated inside living cells, which leads to turn-on emission and is applied for photoresponsive cell imaging. This marks the first report of a light-triggered [2 + 2]-cycloreversion phenomenon occurring inside a live cell, leading to cell imaging. Moreover, the synthesized drug derivatives were utilized for synchronous cell imaging as well as drug delivery through the developed [2 + 2]-photocycloreversion process, which demonstrated the potential applicability of this class of molecules.

Source: Chemical Science

DOI: 10.1039/d4sc07817a

Authors: Sanhati Sharangi, Barsha Chakraborty, Raushan Kumar Jha, Swarnadeep Mandal, Apurba Lal Koner, Sangit Kumar

Institution: Indian Institute of Science Education and Research, Bhopal

Language: English

Topic: Photochromic and Fluorescence Chemistry

Subfield: Materials Chemistry

Field: Materials Science

Domain: Physical Sciences

Open Access status: diamond

Funders: Department of Science and Technology, Ministry of Science and Technology, India, Indian Institute of Science Education and Research Bhopal, Indian Institute of Science Education and Research Mohali, Science and Engineering Research Board

Awards: G275237448, G5694829756, G6319186174