Naphth[1,2- d ]imidazoles Bioactive from β-Lapachone: Fluorescent Probes and Cytotoxic Agents to Cancer Cells

• Published in: Molecules (Basel, Switzerland) Switzerland), 2023-03, Vol.28 (7), p.3008
• Main Authors: Santos, Victória Laysna Dos Anjos, Gonsalves, Arlan de Assis, Guimarães, Délis Galvão, Simplicio, Sidney Silva, Oliveira, Helinando Pequeno de, Ramos, Lara Polyana Silva, Costa, Marcília Pinheiro da, Oliveira, Fátima de Cássia Evangelista de, Pessoa, Claudia, Araújo, Cleônia Roberta Melo
• Format: Article
• Language: English
• Subjects: Absorptivity; anticancer; Antineoplastic Agents - pharmacology; Biocompatibility; Biological activity; Biomedical materials; Cancer; Cancer cells; Carbon; Cytotoxic agents; Cytotoxicity; Cytotoxins; Diagnostic agents; Emissions; Fluorescence; Fluorescent Dyes - pharmacology; Fluorescent indicators; fluorescent probe; heterocycle; Humans; Imidazole; Imidazoles - pharmacology; Lapachone; Leukemia; Medical imaging; naphthoimidazole; Neoplasms; NMR; Nuclear magnetic resonance; Optical properties; Pharmacokinetics; Pharmacology; Precision medicine; Probes; Solvents; Structure-Activity Relationship; theranostic
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules28073008

Theranostics combines therapeutic and imaging diagnostic techniques that are extremely dependent on the action of imaging agent, transporter of therapeutic molecules, and specific target ligand, in which fluorescent probes can act as diagnostic agents. In particular, naphthoimidazoles are potential bioactive heterocycle compounds to be used in several biomedical applications. With this aim, a group of seven naphth[1,2- ]imidazole compounds were synthesized from β-lapachone. Their optical properties and their cytotoxic activity against cancer cells and their compounds were evaluated and confirmed promising values for molar absorptivity coefficients (on the order of 10 to 10 ), intense fluorescence emissions in the blue region, and large Stokes shifts (20-103 nm). Furthermore, the probes were also selective for analyzed cancer cells (leukemic cells (HL-60). The naphth[1,2- ]imidazoles showed IC between 8.71 and 29.92 μM against HL-60 cells. For HCT-116 cells, values for IC between 21.12 and 62.11 μM were observed. The selective cytotoxicity towards cancer cells and the fluorescence of the synthesized naphth[1,2- ]imidazoles are promising responses that make possible the application of these components in antitumor theranostic systems.