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Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift
- Source :
- Molecules, Volume 26, Issue 9, Molecules, Vol 26, Iss 2679, p 2679 (2021)
- Publication Year :
- 2021
- Publisher :
- MDPI, 2021.
-
Abstract
- BODIPY dyes are photostable neutral derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene. These are widely used as chemosensors, laser materials, and molecular probes. At the same time, BODIPY dyes have small or moderate Stokes shifts like most other fluorophores. Large Stokes shifts are preferred for fluorophores because of higher sensitivity of such probes and sensors. The new boron containing BODIPY dye was designed and synthesized. We succeeded to perform an annulation of pyrrole ring with coumarin heterocyclic system and achieved a remarkable difference in absorption and emission maximum of obtained fluorophore up to 100 nm. This BODIPY dye was equipped with linker arm and was functionalized with a maleimide residue specifically reactive towards thiol groups of proteins. BODIPY residue equipped with a suitable targeting protein core can be used as a suitable imaging probe and agent for Boron Neutron Capture Therapy (BNCT). As the most abundant protein with a variety of physiological functions, human serum albumin (HSA) has been used extensively for the delivery and improvement of therapeutic molecules. Thiolactone chemistry provides a powerful tool to prepare albumin-based multimodal constructions. The released sulfhydryl groups of the homocysteine functional handle in thiolactone modified HSA were labeled with BODIPY dye to prepare a labeled albumin-BODIPY dye conjugate confirmed by MALDI-TOF-MS, UV-vis, and fluorescent emission spectra. Cytotoxicity of the resulting conjugate was investigated. This study is the basis for a novel BODIPY dye-albumin theranostic for BNCT. The results provide further impetus to develop derivatives of HSA for delivery of boron to cancer cells.
- Subjects :
- Boron Compounds
Spectrometry, Mass, Electrospray Ionization
Fluorophore
BODIPY dye with a large stokes shift
theranostic
Pharmaceutical Science
HSA
Boron Neutron Capture Therapy
Serum Albumin, Human
Article
Analytical Chemistry
Maleimides
chemistry.chemical_compound
symbols.namesake
Lactones
QD241-441
Drug Delivery Systems
Stokes shift
Neoplasms
Drug Discovery
Thiolactone
medicine
Humans
Physical and Theoretical Chemistry
Precision Medicine
Coloring Agents
Maleimide
Homocysteine
Fluorescent Dyes
N-trifluoroacetylhomocysteine thiolactone
Organic Chemistry
Human serum albumin
Combinatorial chemistry
Fluorescence
Spectrometry, Fluorescence
chemistry
Chemistry (miscellaneous)
Molecular Probes
symbols
Molecular Medicine
biopolymer labelling
Spectrophotometry, Ultraviolet
BODIPY
Conjugate
medicine.drug
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 26
- Issue :
- 9
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....634d102e67d279ea4f1d7b20bae95b48