Comparative Investigation of the Chemiluminescent Properties of a Dibrominated Coelenterazine Analog

• Type: Article in International Scientific Journal
• Date: 2022-07-30

Authors

Luís Pinto da Silva (Author) FCUP; João Sousa (Author) Other; Carla M. Magalhães (Author) FCUP; Patricia González-Berdullas (Author) FCUP; Joaquim C G E Esteves da Silva (Author) FCUP

Journal

Title: International Journal Of Molecular Sciences

Vol. 23

Pages: 8490-8490

ISSN: 1661-6596

Publisher: MDPI

Indexing

ISI Web of Knowledge - 3 Citations

Scopus

Associated Projects

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

Other information

Authenticus ID: P-00W-ZMS

DOI: 10.3390/ijms23158490

Abstract (EN): Chemi- and bioluminescence are remarkable light-emitting phenomena, in which thermal energy is converted into excitation energy due to a (bio)chemical reaction. Among a wide variety of chemi-/bioluminescent systems, one of the most well-known and studied systems is that of marine imidazopyrazinones, such as Coelenterazine and Cypridina luciferin. Due to the increasing usefulness of their chemi-/bioluminescent reactions in terms of imaging and sensing applications, among others, significant effort has been made over the years by researchers to develop new derivatives with enhanced properties. Herein, we report the synthesis and chemiluminescent characterization of a novel dibrominated Coelenterazine analog. This novel compound consistently showed superior luminescence, in terms of total light output and emission lifetime, to natural imidazopyrazinones and commercially available analogs in aprotic media, while being capable of yellow light emission. Finally, this new compound showed enhanced chemiluminescence in an aqueous solution when triggered by superoxide anion, showing potential to be used as a basis for optimized probes for reactive oxygen species. In conclusion, bromination of the imidazopyrazinone scaffold appears to be a suitable strategy for obtaining Coelenterazines with enhanced properties.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 13