BIOMAT Database Logo BIOMAT Database Logo

Tetracyclic Thioxanthene Derivatives: Studies on Fluorescence and Antitumor Activity. 2021

Fernando Durães, and Patrícia M A Silva, and Pedro Novais, and Isabel Amorim, and Luís Gales, and Cátia I C Esteves, and Samuel Guieu, and Hassan Bousbaa, and Madalena Pinto, and Emília Sousa
Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal.

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 GI50 values below 10 µM 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.

UI MeSH Term Description Entries
D011799 Quinazolines A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring. Quinazoline
D004354 Drug Screening Assays, Antitumor Methods of investigating the effectiveness of anticancer cytotoxic drugs and biologic inhibitors. These include in vitro cell-kill models and cytostatic dye exclusion tests as well as in vivo measurement of tumor growth parameters in laboratory animals. Anticancer Drug Sensitivity Tests,Antitumor Drug Screens,Cancer Drug Tests,Drug Screening Tests, Tumor-Specific,Dye Exclusion Assays, Antitumor,Anti-Cancer Drug Screens,Antitumor Drug Screening Assays,Tumor-Specific Drug Screening Tests,Anti Cancer Drug Screens,Anti-Cancer Drug Screen,Antitumor Drug Screen,Cancer Drug Test,Drug Screen, Anti-Cancer,Drug Screen, Antitumor,Drug Screening Tests, Tumor Specific,Drug Screens, Anti-Cancer,Drug Screens, Antitumor,Drug Test, Cancer,Drug Tests, Cancer,Screen, Anti-Cancer Drug,Screen, Antitumor Drug,Screens, Anti-Cancer Drug,Screens, Antitumor Drug,Test, Cancer Drug,Tests, Cancer Drug,Tumor Specific Drug Screening Tests
D005453 Fluorescence The property of emitting radiation while being irradiated. The radiation emitted is usually of longer wavelength than that incident or absorbed, e.g., a substance can be irradiated with invisible radiation and emit visible light. X-ray fluorescence is used in diagnosis.
D006131 Growth Inhibitors Endogenous or exogenous substances which inhibit the normal growth of human and animal cells or micro-organisms, as distinguished from those affecting plant growth ( Cell Growth Inhibitor,Cell Growth Inhibitors,Growth Inhibitor,Growth Inhibitor, Cell,Growth Inhibitors, Cell,Inhibitor, Cell Growth,Inhibitor, Growth,Inhibitors, Cell Growth,Inhibitors, Growth
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013892 Thioxanthenes Compounds with three aromatic rings in linear arrangement with a SULFUR in the center ring.
D044004 Xanthones A group of XANTHENES that contain a 9-keto OXYGEN. Xanthone Derivatives,Derivatives, Xanthone
D045744 Cell Line, Tumor A cell line derived from cultured tumor cells. Tumor Cell Line,Cell Lines, Tumor,Line, Tumor Cell,Lines, Tumor Cell,Tumor Cell Lines

Related Publications

Fernando Durães, and Patrícia M A Silva, and Pedro Novais, and Isabel Amorim, and Luís Gales, and Cátia I C Esteves, and Samuel Guieu, and Hassan Bousbaa, and Madalena Pinto, and Emília Sousa
Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines.
August 1992, Journal of medicinal chemistry,
Fernando Durães, and Patrícia M A Silva, and Pedro Novais, and Isabel Amorim, and Luís Gales, and Cátia I C Esteves, and Samuel Guieu, and Hassan Bousbaa, and Madalena Pinto, and Emília Sousa
Synthesis and antitumor activity of fused tetracyclic quinoline derivatives. 1.
June 1989, Journal of medicinal chemistry,
Fernando Durães, and Patrícia M A Silva, and Pedro Novais, and Isabel Amorim, and Luís Gales, and Cátia I C Esteves, and Samuel Guieu, and Hassan Bousbaa, and Madalena Pinto, and Emília Sousa
[New thioxanthene derivatives with central nervous activity].
June 1971, Il Farmaco; edizione scientifica,
Fernando Durães, and Patrícia M A Silva, and Pedro Novais, and Isabel Amorim, and Luís Gales, and Cátia I C Esteves, and Samuel Guieu, and Hassan Bousbaa, and Madalena Pinto, and Emília Sousa
[CHEMICAL AND CHEMOTHERAPEUTICAL STUDIES ON THE FURAN DERIVATIVES. XXXIV. ANTITUMOR ACTIVITY OF NITROFURANQUINOLINE DERIVATIVES].
April 1964, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan,
Fernando Durães, and Patrícia M A Silva, and Pedro Novais, and Isabel Amorim, and Luís Gales, and Cátia I C Esteves, and Samuel Guieu, and Hassan Bousbaa, and Madalena Pinto, and Emília Sousa
Synthesis, Antitumor Activity and Molecular Docking Studies on Seven Novel Thiazacridine Derivatives.
January 2020, Combinatorial chemistry & high throughput screening,
Fernando Durães, and Patrícia M A Silva, and Pedro Novais, and Isabel Amorim, and Luís Gales, and Cátia I C Esteves, and Samuel Guieu, and Hassan Bousbaa, and Madalena Pinto, and Emília Sousa
Studies on RA derivatives. V. Synthesis and antitumor activity of Ala2-modified RA-VII derivatives.
August 1993, Chemical & pharmaceutical bulletin,
Fernando Durães, and Patrícia M A Silva, and Pedro Novais, and Isabel Amorim, and Luís Gales, and Cátia I C Esteves, and Samuel Guieu, and Hassan Bousbaa, and Madalena Pinto, and Emília Sousa
Selective oxidation of thioxanthene derivatives.
January 1986, Acta pharmaceutica Suecica,
Fernando Durães, and Patrícia M A Silva, and Pedro Novais, and Isabel Amorim, and Luís Gales, and Cátia I C Esteves, and Samuel Guieu, and Hassan Bousbaa, and Madalena Pinto, and Emília Sousa
Inhibitory activity evaluation and mechanistic studies of tetracyclic oxindole derivatives as α-glucosidase inhibitors.
November 2016, European journal of medicinal chemistry,
Fernando Durães, and Patrícia M A Silva, and Pedro Novais, and Isabel Amorim, and Luís Gales, and Cátia I C Esteves, and Samuel Guieu, and Hassan Bousbaa, and Madalena Pinto, and Emília Sousa
[Studies on furan derivatives. XI. Test for antitumor activity of nitrofuran derivatives (author's transl)].
January 1981, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan,
Fernando Durães, and Patrícia M A Silva, and Pedro Novais, and Isabel Amorim, and Luís Gales, and Cátia I C Esteves, and Samuel Guieu, and Hassan Bousbaa, and Madalena Pinto, and Emília Sousa
Flavoenzyme-mediated reduction reactions and antitumor activity of nitrogen-containing tetracyclic ortho-quinone compounds and their nitrated derivatives.
January 2017, EXCLI journal,
Copied contents to your clipboard!