Please use this identifier to cite or link to this item: https://hdl.handle.net/10316/81178
Title: Synthesis, Structure, and Cytotoxicity of a New Sulphanyl-Bridged Thiadiazolyl-Saccharinate Conjugate: The Relevance of S···N Interaction
Authors: Cabral, Lília I. L. 
Brás, Elisa M. 
Henriques, Marta S. C. 
Marques, Cátia 
Frija, Luís M. T. 
Barreira, Luísa 
Paixão, José António 
Fausto, Rui 
Issue Date: 2-Mar-2018
Publisher: Wiley
Project: PTDC/QEQ‐QFI/3284/2014 
PTDC/MAR‐BIO/4132/2014, 
UID/FIS/04564/2016 
Serial title, monograph or event: Chemistry - A European Journal
Volume: 24
Abstract: Reports showing that the copper concentration is considerably higher in neoplasms than in normal tissues prompted the need to develop selective copper chelators. We disclosed recently that some N-linked tetrazole-saccharinates bind selectively to copper, forming complexes that are highly cytotoxic towards cancer cells. Because tetrazole-saccharinates are photolabile, due to the photoreactivity of tetrazoles, we proposed thiadiazolyl-saccharinates as an alternative. Herein we describe the synthesis, structure, and monomeric photochemistry of a sulphanyl-bridged thiadiazolylsaccharinate, 3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulphanyl]-1,2-benzothiazole 1,1-dioxide (MTSB). The monomeric structure, charge density analysis, and characteristic infrared spectrum of MTSB were investigated theoretically, using quantum chemical calculations, and also experimentally, using matrixisolation infrared spectroscopy. The crystal structure was investigated by combining X-ray crystallography with infrared and Raman spectroscopies. Results show that the structure of isolated MTSB is similar to that found in the crystal, with an S···N interaction clearly contributing to the structure of the molecule and of the crystal. Matrix irradiation revealed a high phot ostability of MTSB, compared to parent tetrazolesaccharinates and to the 5-methyl-1,3,4-thiadiazole building block, emphasizing the photostabilizing effect of the saccharyl system. Finally, in vitro toxicity assays of MTSB showed a copper concentration-dependent toxicity against cancer cells, without affecting normal cells. In particular, MTSB was most effective towards the hepatic (HepG2), neuroblastoma (SH-SY5), and lymphoma cell lines (U937). Thus, MTSB represents a promising lead for cancer chemotherapy based on chelating agents
URI: https://hdl.handle.net/10316/81178
DOI: 10.1002/chem.201705319
Rights: embargoedAccess
Appears in Collections:I&D CFis - Artigos em Revistas Internacionais

Files in This Item:
File Description SizeFormat
Cabral_et_al-2018-Chemistry_-_A_European_Journal.pdf2.26 MBAdobe PDFView/Open
Show full item record

SCOPUSTM   
Citations

5
checked on May 1, 2023

WEB OF SCIENCETM
Citations 10

5
checked on Mar 2, 2024

Page view(s)

281
checked on Mar 26, 2024

Download(s)

376
checked on Mar 26, 2024

Google ScholarTM

Check

Altmetric

Altmetric


This item is licensed under a Creative Commons License Creative Commons