Combined Experimental and Theoretical Investigation into the Photophysical Properties of Halogenated Coelenteramide Analogs

• Tipo: Artigo em Revista Científica Internacional
• Data: 2022

Autores

Afonso, ACP (Autor) Outra; Gonzalez-Berdullas, P (Autor) Outra; Joaquim C G E Esteves da Silva (Autor) FCUP; da Silva, LP (Autor) FCUP

Revista

Título: Molecules

Vol. 33

Página Final: 8875

ISSN: 1420-3049

Editora: MDPI

Indexação

ISI Web of Knowledge - 3 Citações

Scopus - 3 Citações

Projetos Associados

ChemiTumorTher - Quimioluminescência Marinha como uma Terapia Anticancro de Amplo Espectro com uma Selectividade e Actividade Tumoral Melhorada

Outras Informações

ID Authenticus: P-00X-KFP

DOI: 10.3390/molecules27248875

Abstract (EN): Marine Coelenterazine is one of the most well-known chemi-/bioluminescent systems, and in which reaction the chemi-/bioluminophore (Coelenteramide) is generated and chemiexcited to singlet excited states (leading to light emission). Recent studies have shown that the bromination of compounds associated with the marine Coelenterazine system can provide them with new properties, such as anticancer activity and enhanced emission. Given this, our objective is to characterize the photophysical properties of a previously reported brominated Coelenteramide analog, by employing a combined experimental and theoretical approach. To better analyze the potential halogen effect, we have also synthesized and characterized, for the first time, two new fluorinated and chlorinated Coelenteramide analogs. These compounds show similar emission spectra in aqueous solution, but with different fluorescence quantum yields, in a trend that can be correlated with the heavy-atom effect (F > Cl > Br). A blue shift in emission in other solvents is also verified with the F-Cl-Br trend. More relevantly, the fluorescence quantum yield of the brominated analog is particularly sensitive to changes in solvent, which indicates that this compound has potential use as a microenvironment fluorescence probe. Theoretical calculations indicate that the observed excited state transitions result from local excitations involving the pyrazine ring. The obtained information should be useful for the further exploration of halogenated Coelenteramides and their luminescent properties.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 11