Tetracyclic Thioxanthene Derivatives: Studies on Fluorescence and Antitumor Activity

• Type: Article in International Scientific Journal
• Date: 2021

Authors

Durães, F (Author) Other; Silva, PMA (Author) Other; Novais, P (Author) Other; Amorim, I (Author) Other; Luis Gales (Author) ICBAS; Esteves, CIC (Author) Other; Guieu, S (Author) Other; Bousbaa, H (Author) Other; Maria Isabel Amorim (Author) FCUP; Emilia Sousa (Author) FFUP

Journal

Title: Molecules

Vol. 26 No. 17

Final page: 3315

ISSN: 1420-3049

Publisher: MDPI

Indexing

ISI Web of Knowledge - 1 Citation

Scopus - 1 Citation

Other information

Authenticus ID: P-00V-1T5

DOI: 10.3390/molecules26113315

Abstract (EN): Thioxanthones are bioisosteres of the naturally occurring xanthones. They have been described for multiple activities, including antitumor. As such, the synthesis of a library of thioxanthones was pursued, but unexpectedly, four tetracyclic thioxanthenes with a quinazoline-chromene scaffold were obtained. These compounds were studied for their human tumor cell growth inhibition activity, in the cell lines A375-C5, MCF-7 and NCI-H460. Photophysical studies were also performed. Two of the compounds displayed GI(50) values below 10 mu M for the three tested cell lines, and structure-activity relationship studies were established. Three compounds presented similar wavelengths of absorption and emission, characteristic of dyes with a push-pull character. The structures of two compounds were elucidated by X-ray crystallography. Two tetracyclic thioxanthenes emerged as hit compounds. One of the two compounds accumulated intracellularly as a bright fluorescent dye in the green channel, as analyzed by both fluorescence microscopy and flow cytometry, making it a promising theranostic cancer drug candidate.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 13