학술논문
Microwave-assisted synthesis of meso -carboxyalkyl-BODIPYs and an application to fluorescence imaging.
Document Type
Academic Journal
Author
Mhlongo NZ; Catalysis and Peptide Research Unit, University of KwaZulu-Natal, Durban, South Africa. naickert1@ukzn.ac.za.; Ebenhan T; Driver CHS; Maguire GEM; Kruger HG; Govender T; Naicker T
Source
Publisher: Royal Society of Chemistry Country of Publication: England NLM ID: 101154995 Publication Model: Print Cited Medium: Internet ISSN: 1477-0539 (Electronic) Linking ISSN: 14770520 NLM ISO Abbreviation: Org Biomol Chem Subsets: PubMed not MEDLINE; MEDLINE
Subject
Language
English
Abstract
In this study, a significantly improved method for the synthesis of modular meso-BODIPY (boron dipyrromethene) derivatives possessing a free carboxylic acid group (which was subsequently coupled to peptides), is disclosed. This method provides a vastly efficient synthetic route with a > threefold higher overall yield than other reports. The resultant meso-BODIPY acid allowed for further easy incorporation into peptides. The meso-BODIPY peptides showed absorption maxima from 495-498 nm and emission maxima from 504-506 nm, molar absorptivity coefficients from 33 383-80 434 M-1 cm-1 and fluorescent quantum yields from 0.508-0.849. The meso-BODIPY-c(RGDyK) peptide was evaluated for plasma stability and (proved to be durable even up to 4 h) was then assessed for its fluorescence imaging applicability in vivo and ex vivo. The optical imaging in vivo was limited due to autofluorescence, however, the ex vivo tissue analysis displayed BODIPY-c(RGDyK) internalization and cancer detection thereby making it a novel tumor-integrin associated fluorescent probe while displaying the lack of interference the dye has on the properties of this ligand to bind the receptor.