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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Hybrid 3,4-dihydropyrimidin-2-(thi)ones as dual-functional bioactive molecules: fluorescent probes and cytotoxic agents to cancer cells

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Author(s):
de Souza, Vanessa P. [1] ; Santos, Fabiano S. [2] ; Rodembusch, Fabiano S. [2] ; Braga, Carolyne B. [3] ; Ornelas, Catia [3] ; Pilli, Ronaldo A. [3] ; Russowsky, Dennis [1]
Total Authors: 7
Affiliation:
[1] Univ Fed Rio Grande do Sul, Inst Quim, Lab Sinteses Organ, Av Bento Goncalves 9500, BR-91501970 Porto Alegre, RS - Brazil
[2] Univ Fed Rio Grande do Sul, Inst Quim, Grp Pesquisa Fotoquim Organ Aplicada, Av Bento Goncalves 9500, BR-91501970 Porto Alegre, RS - Brazil
[3] Univ Estadual Campinas, Inst Quim, BR-13084971 Campinas, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: NEW JOURNAL OF CHEMISTRY; v. 44, n. 29, p. 12440-12451, AUG 7 2020.
Web of Science Citations: 0
Abstract

A series of new hybrid fluorescent Biginelli compounds, including a Monastrol derivative, were designed and synthesized with good yields. The photophysical studies revealed dual fluorescence emission, attributed to excited enol forms (E{*}) and tautomeric (K{*}) species, respectively, due to the ESIPT mechanism. The cytotoxic activity of all compounds was evaluated against MCF-7, Caco-2 and PC3 cancer cell lines and PNT2 normal prostate cells. The fluorescent Monastrol derivative8fwas the most active with cytotoxic activity very similar to cisplatin, whereas derivative8cwas the most selective towards the PC3 prostate cancer cells. The confocal laser scanning microscopy images of PC3 and MCF-7 cancer cell lines were acquired after incubation of the fluorescent Biginelli hybrids8cand8f, respectively, demonstrating efficient cellular uptake of both compounds and strong fluorescence within the intracellular medium. These results show that the new hybrid 3,4-dihydropyrimidin-2-(thi)ones are dual-function bioactive compounds that act both as fluorescent probes and antineoplastic agents. (AU)

FAPESP's process: 17/06146-8 - Development of nanocarriers based on dendrimers and polymer nanoparticles for selective delivery of goniothalamin, piplartine and Monastrol
Grantee:Carolyne Brustolin Braga
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 19/13104-5 - Planning and synthesis of inhibitors based on biological targets: the case of neglected kinases
Grantee:Ronaldo Aloise Pilli
Support Opportunities: Regular Research Grants
FAPESP's process: 18/02093-0 - Development of new nanomaterials for nanomedicine applications
Grantee:Cátia Cristina Capêlo Ornelas Megiatto
Support Opportunities: Regular Research Grants