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Silicon Phthalocyanines for Photodynamic Therapy Studies

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2008, Doctor of Philosophy, Case Western Reserve University, Chemistry.
Four sulfonated silicon phthalocyanines SiPc(1-SO3H)[OSi(n-C6H13)3]2, 2, Pc 177; SiPc(2-SO3H)[OSi(n-C6H13)3]2, 4, Pc 178; SiPc(1-SO3H)[OSi(CH3)2(CH2)3N(CH3)2]2, 3, Pc 179; and SiPc(2-SO3H)[OSi(CH3)2(CH2)3N(CH3)2]2, 5, Pc 180, were prepared and characterized. The first two were made for an abandoned external study and the second two for an internal photodynamic therapy (PDT) study. In further work, acid SiPc[OSi(CH3)2(CH2)10C(O)OH]2, 28, Pc 61 was prepared and was conjugated with trimer H(C9H10N2O2)3OCH3, 15, a trimer first synthesized by Hamilton. This trimer has the potential to bind to Bcl-2 and Bcl-xL proteins (proteins which are overexpressed in cancer cells). The two conjugates obtained, SiPc[OSi(CH3)2(CH2)10C(O)(C9H10N2O2)3OCH3]2, 30, Pc 212; and HOSiPcOSi(CH3)2(CH2)10C(O)(C9H10N2O2)3OCH3, 31, Pc 213, have the potential to complex with the Bcl-2 and Bcl-xL through their aminotrimer units and with photodynamic action to destroy these proteins and their associated cancer cells. Also, two alkyl silicon phthalocyanines, HS(CH2)3SiPcOSi(CH3)2(CH2)3N(CH3)2, 52, Pc 227; and CH3S(CH2)3SiPcOSi(CH3)2(CH2)3N(CH3)2, 58, Pc 223, were prepared as “masked Pc 4s”. These two alkyl phthalocyanines have the potential to bind to Au nanoparticles through their SH and SCH3 functional groups respectively. xviii The phthalocyanine-Au nanoparticle conjugates appear to have the potential to target tumor tissues, and when irradiated with red light in the presence of H2O and O2 to yield Pc 4. Pc 4 has the ability to destroy the tumor tissues when used in PDT.
Malcolm Kenney (Advisor)

Recommended Citations

Citations

  • Li, J. (2008). Silicon Phthalocyanines for Photodynamic Therapy Studies [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1193850866

    APA Style (7th edition)

  • Li, Jun. Silicon Phthalocyanines for Photodynamic Therapy Studies. 2008. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1193850866.

    MLA Style (8th edition)

  • Li, Jun. "Silicon Phthalocyanines for Photodynamic Therapy Studies." Doctoral dissertation, Case Western Reserve University, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=case1193850866

    Chicago Manual of Style (17th edition)