Efficient deprotection and demetallation of a chlorin photosensitizer followed by microwave addition of an alkyl amine linker
Research Mentor(s)
Vannelli, Tommaso A.
Description
Photodynamic therapy (PDT) is a method of cancer and antibacterial treatment that uses a photosensitizer coupled with a specific wavelength of light to produce reactive species resulting in cell death. The reported deprotection and demetallation experiments show improved conditions, reaction times, and purity compared to previously reported data. Microwave assisted addition of Fmoc-diaminobutane to produce an amide linker on the benzoic acid substituent of the chlorin was also performed. The amide bond was found to form efficiently via the n-hydroxysuccinimide (NHS) ester chlorin derivative, and standard coupling techniques of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI), and 4-dimethylaminopyridine (DMAP) were used in the linker synthesis. The final product was purified via column chromatography and characterized by 1H NMR, DQCOSY 2D 1H NMR and LCMS. The future of this project is to link this compound to a siderophore, pyoverdine, for use in targeted antibacterial PDT applications. The bacteria will uptake this complex, thereby activating it, and creating the reactive species, signlet oxygen, ultimately killing the bacteria.
Document Type
Event
Start Date
15-5-2015 10:00 AM
End Date
15-5-2015 2:00 PM
Department
Chemistry
Genre/Form
student projects; posters
Subjects – Topical (LCSH)
Cancer--Photochemotherapy; Bacterial diseases--Treatment
Type
Image
Rights
Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this documentation for commercial purposes, or for financial gain, shall not be allowed without the author's written permission.
Language
English
Format
application/pdf
Efficient deprotection and demetallation of a chlorin photosensitizer followed by microwave addition of an alkyl amine linker
Photodynamic therapy (PDT) is a method of cancer and antibacterial treatment that uses a photosensitizer coupled with a specific wavelength of light to produce reactive species resulting in cell death. The reported deprotection and demetallation experiments show improved conditions, reaction times, and purity compared to previously reported data. Microwave assisted addition of Fmoc-diaminobutane to produce an amide linker on the benzoic acid substituent of the chlorin was also performed. The amide bond was found to form efficiently via the n-hydroxysuccinimide (NHS) ester chlorin derivative, and standard coupling techniques of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI), and 4-dimethylaminopyridine (DMAP) were used in the linker synthesis. The final product was purified via column chromatography and characterized by 1H NMR, DQCOSY 2D 1H NMR and LCMS. The future of this project is to link this compound to a siderophore, pyoverdine, for use in targeted antibacterial PDT applications. The bacteria will uptake this complex, thereby activating it, and creating the reactive species, signlet oxygen, ultimately killing the bacteria.