Long-range excited-state intramolecular proton transfer (ESIPT)-assisted two-photon responsive COS/H₂S donor: a nanoprodrug for cancer treatment.

Authors

Suchhanda Biswas, Arijit Kumar Mondal, Subham Pal, Manotosh Pramanik, Bipul Pal, Asoke P Chattopadhyay, Batakrishna Jana, N D Pradeep Singh

Published in

Journal of materials chemistry. B. Jul 20, 2026. Epub Jul 20, 2026.

Abstract

Recently, hydrogen sulfide (H₂S) has been recognised as a promising member of the gasotransmitter family, which plays a vital role in regulating various physiological and pathological processes. Hence, the development of synthetic chemical tools capable of donating H₂S in a controlled manner is an area of substantial interest. Herein, we developed a two-photon-activated photoresponsive COS/H₂S donor that exploits the long-range excited-state intramolecular proton transfer (ESIPT) phenomenon in our designed system. This platform uses a photocage tethered to a thiocarbamate moiety, which, upon light irradiation, releases COS. The released COS could be rapidly hydrolysed by carbonic anhydrase and generate H₂S, closely mimicking the body's well-regulated endogenous H₂S production. Additionally, the incorporation of the long-range ESIPT process offers several advantages, such as (i) strong emission with a large Stokes shift and (ii) a faster photorelease rate. TD-DFT calculations carried out using the CAM-B3LYP density functional with the TZVP basis set further validated our experimental findings. Intrigued by these properties, we also developed our photoresponsive COS/H₂S donor HQ-COS as a nanoprodrug (nano-HQCOS) and explored its therapeutic potential in the MDA-MB-231 triple-negative breast cancer cell line. In vitro studies demonstrated that our nano-HQCOS exhibits effective cellular internalisation and inhibits the growth of triple-negative breast cancer cells, particularly those with overexpressed carbonic anhydrase, while it is benign to the normal healthy cells.

PMID:
42475119
Bibliographic data and abstract were imported from PubMed on 20 Jul 2026.

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