- Title
- The preparation of BODIPY and porphyrin dyes and their cyclodextrin inclusion complexes and Pluronic® F-127 encapsulation micelles for use in PDT and PACT
- Creator
- Molupe, Nthabeleng
- ThesisAdvisor
- Mack, John
- ThesisAdvisor
- Nyokong, Tebello
- Subject
- Dyes and dyeing -- Chemistry
- Subject
- Drug delivery systems
- Subject
- Fluorescence spectroscopy
- Subject
- Cancer -- Photochemotherapy
- Subject
- Photosensitizing compounds -- Therapeutic use
- Subject
- Cyclodextrins -- Biotechnology
- Subject
- Nanoparticles
- Date
- 2019
- Type
- text
- Type
- Thesis
- Type
- Masters
- Type
- MSc
- Identifier
- http://hdl.handle.net/10962/117574
- Identifier
- vital:34528
- Description
- Several novel BODIPY dyes ((4,4′-difluoro-1,7-tetramethyl-3,5-(3-dithiophene)-2,6-diiodo-8-(4-dimethylamino)-4-bora-3a,4a-diaza-s-indacene (1c), 4,4′-difluoro-1,7-tetramethyl-3,5-(3 dithiophene)-2,6-diiodo-8-(4-methylthio)-4-bora-3a,4a-diaza-s-indacene (3c) and 4,4′-difluoro-1,7-tetramethyl-3,5-(4-dibenzyloxybenzene)-2,6-diiodo-8-(4-methylbenzoate)-4 bora-3a,4a-diaza-s-indacene (4c)) and porphyrins (tetraacenaphthylporphyrin (7a) and Sn(IV) tetraacenaphthylporphyrin (7b)) were synthesized and characterized. Previously reported BODIPY dyes (4,4′-difluoro-1,7-tetramethyl-3,5-(2-dihydroxy)-2,6-diiodo-8-(4-bromo)-4-bora-3a,4a-diaza-s-indacene (5) and 4,4′-difluoro-1,7-tetramethyl-3,5-(2-dithiophene)-2,6-diiodo-8-(phenyl)-4-bora-3a,4a-diaza-s-indacene (6)) were also used. Pluronic® F-127 and cyclodextrins were used as solubilizing drug delivery agents for the synthesized BODIPY dyes. The encapsulation of BODIPY dyes with Pluronic® F-127 micelles improved the water solubility of the BODIPY 5. Further modification of Pluronic® F-127 by coating with folate-functionalized chitosan for targeted delivery of BODIPY 1c and 6 was explored. The BODIPY dyes and their encapsulation complexes exhibited significant inhibition of human MCF-7 breast cancer cell growth. When cyclodextrins were used as nanocarriers, the inclusion complexes of BODIPY 4c with mβCD were found to enhance the water-solubility of the dye. Greater photoinactivation of Staphylococcus aureus was observed for the inclusion complexes when compared to the effect of solutions of non-complexed BODIPY 4c. The cyclodextrin inclusion complexes of porphyrin 7b with mβCD were also found to enhance the water-solubility of 7b. When the photodynamic effect was evaluated, solutions of the porphyrin alone and their inclusion complexes were found to have significant photodynamic effects against human MCF-7 breast cancer cells.
- Format
- 202 Leaves, pdf
- Publisher
- Rhodes University, Faculty of Science, Chemistry
- Language
- English
- Rights
- Molupe, Nthabeleng Regina
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| Thumbnail | File | Description | Size | Format | |||
|---|---|---|---|---|---|---|---|
| View Details Download | SOURCE1 | MOLUPE-MSc-TR20-54.pdf | 6 MB | Adobe Acrobat PDF | View Details Download |