Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift
BODIPY dyes are photostable neutral derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-<i>s</i>-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 Stoke...
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MDPI AG
2021-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/9/2679 |
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| author | Valeria I. Raskolupova Tatyana V. Popova Olga D. Zakharova Anastasia E. Nikotina Tatyana V. Abramova Vladimir N. Silnikov |
| author_facet | Valeria I. Raskolupova Tatyana V. Popova Olga D. Zakharova Anastasia E. Nikotina Tatyana V. Abramova Vladimir N. Silnikov |
| author_sort | Valeria I. Raskolupova |
| collection | DOAJ |
| description | BODIPY dyes are photostable neutral derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-<i>s</i>-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. |
| first_indexed | 2024-03-10T11:43:55Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T11:43:55Z |
| publishDate | 2021-05-01 |
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| series | Molecules |
| spelling | doaj.art-ff587c9b477e42efb194898d94ef808b2023-11-21T18:16:23ZengMDPI AGMolecules1420-30492021-05-01269267910.3390/molecules26092679Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes ShiftValeria I. Raskolupova0Tatyana V. Popova1Olga D. Zakharova2Anastasia E. Nikotina3Tatyana V. Abramova4Vladimir N. Silnikov5Institute of Chemical Biology and Fundamental Medicine SB RAS, Lavrent’ev Ave, 8, 630090 Novosibirsk, RussiaInstitute of Chemical Biology and Fundamental Medicine SB RAS, Lavrent’ev Ave, 8, 630090 Novosibirsk, RussiaInstitute of Chemical Biology and Fundamental Medicine SB RAS, Lavrent’ev Ave, 8, 630090 Novosibirsk, RussiaInstitute of Chemical Biology and Fundamental Medicine SB RAS, Lavrent’ev Ave, 8, 630090 Novosibirsk, RussiaInstitute of Chemical Biology and Fundamental Medicine SB RAS, Lavrent’ev Ave, 8, 630090 Novosibirsk, RussiaInstitute of Chemical Biology and Fundamental Medicine SB RAS, Lavrent’ev Ave, 8, 630090 Novosibirsk, RussiaBODIPY dyes are photostable neutral derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-<i>s</i>-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.https://www.mdpi.com/1420-3049/26/9/2679BODIPY dye with a large stokes shift<i>N</i>-trifluoroacetylhomocysteine thiolactonebiopolymer labellingHSAtheranostic |
| spellingShingle | Valeria I. Raskolupova Tatyana V. Popova Olga D. Zakharova Anastasia E. Nikotina Tatyana V. Abramova Vladimir N. Silnikov Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift Molecules BODIPY dye with a large stokes shift <i>N</i>-trifluoroacetylhomocysteine thiolactone biopolymer labelling HSA theranostic |
| title | Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift |
| title_full | Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift |
| title_fullStr | Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift |
| title_full_unstemmed | Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift |
| title_short | Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift |
| title_sort | human serum albumin labelling with a new bodipy dye having a large stokes shift |
| topic | BODIPY dye with a large stokes shift <i>N</i>-trifluoroacetylhomocysteine thiolactone biopolymer labelling HSA theranostic |
| url | https://www.mdpi.com/1420-3049/26/9/2679 |
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