CPM-1 Development of Phthalocyanine Glycoconjugates for PDT
Abstract
Photodynamic Therapy (PDT) is a type of phototherapy with possible applications as cancer treatment, antimicrobial, and anti-viral. Phthalocyanines have been shown to be an effective photosensitizer due to their ability to absorb light at a clinically relevant wavelength, which will allow for deeper penetration into tissues. The goal of this study is to develop glycoconjugated phthalocyanines containing a variable carbon chain spacer. Ultimately, we endeavor to create a library of these phthalocyanine glycoconjugates to study the nature of the carbohydrate and if distance from the phthalocyanine impacts the phototherapeutic potential. Phthalocyanines are typically created through a mixed condensation reaction using phthalonitriles. The resulting statistical mixture of products creates a significant challenge in purification and characterization of the products. Utilizing automated flash chromatography, we have been able to purify two desired phthalocyanines; one of which contains an alkyne group directly attached to the phthalocyanine and the other containing a carbon spacer between the alkyne group and phthalocyanine. In both cases, the alkyne group was utilized in a ‘click’ reaction to produce a glycoconjugated phthalocyanine. Using the two established synthetic routes, a library of phthalocyanine glycoconjugates will be constructed. This library will contain glycoconjugated phthalocyanines varying in carbon spacer length. Further work, including MALDI results, will be discussed. This work was supported by funding through SC INBRE/NIH (P20GM103499-20) and an NIH R15 award (1R15GM148916-01).
CPM-1 Development of Phthalocyanine Glycoconjugates for PDT
University Readiness Center Greatroom
Photodynamic Therapy (PDT) is a type of phototherapy with possible applications as cancer treatment, antimicrobial, and anti-viral. Phthalocyanines have been shown to be an effective photosensitizer due to their ability to absorb light at a clinically relevant wavelength, which will allow for deeper penetration into tissues. The goal of this study is to develop glycoconjugated phthalocyanines containing a variable carbon chain spacer. Ultimately, we endeavor to create a library of these phthalocyanine glycoconjugates to study the nature of the carbohydrate and if distance from the phthalocyanine impacts the phototherapeutic potential. Phthalocyanines are typically created through a mixed condensation reaction using phthalonitriles. The resulting statistical mixture of products creates a significant challenge in purification and characterization of the products. Utilizing automated flash chromatography, we have been able to purify two desired phthalocyanines; one of which contains an alkyne group directly attached to the phthalocyanine and the other containing a carbon spacer between the alkyne group and phthalocyanine. In both cases, the alkyne group was utilized in a ‘click’ reaction to produce a glycoconjugated phthalocyanine. Using the two established synthetic routes, a library of phthalocyanine glycoconjugates will be constructed. This library will contain glycoconjugated phthalocyanines varying in carbon spacer length. Further work, including MALDI results, will be discussed. This work was supported by funding through SC INBRE/NIH (P20GM103499-20) and an NIH R15 award (1R15GM148916-01).