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Synthesis and Characterization of New Silicon Phthalocyanines and Nonyl Acridine Orange Analogues for Photodynamic Therapy Studies

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2009, Doctor of Philosophy, Case Western Reserve University, Chemistry.

Two silicon phthalocyanines with diol ligands, SiPc[OSi(CH3)2(CH2)3N(CH3)2][OSi(CH3)2(CH2)4CHOHCH2OH], Pc 181, and SiPc[OSi(CH3)2(CH2)3N(CH3)2][OSi(CH3)2(CH2CHOHCH2OH)], Pc 183, were synthesized by multistep procedures. The cellular uptake, localization and phototoxicity of Pc 181 were assessed by collaborators.

Three silicon phthalocyanines, HSC6H4OSiPcOSi[(CH2)5CH3]3, Pc 253,HS(C6H4)2OSiPcOSi[(CH2)5CH3]3, Pc 254, and HS(C6H4)3OSiPcOSi[(CH2)5CH3]3, Pc 255, were prepared by multistep procedures. These compounds were designed to form conjugates with gold nanoparticles which can be used in quenching studies of phthalocyanine-gold nanoparticle conjugates.

Ten 9-substituted acridine oranges, benz(a)acridine orange, 2-methoxy acridine orange, and two 2-methoxy-9-substituted acridine oranges were prepared and characterized.

From acridine orange, nonyl acridine orange bromide and the other alkyl acridine orange halides were prepared. From the substituted acridine oranges, seven 9-substituted acridine orange halides and one 9-substituted acridine orange triflate were made.

Two of the acridine orange halides gave stronger FRET with Pc 4 than does 10-nonyl acridine orange, and thus are potential probes for cardiolipin in further PDT studies. Work by collaborators showed that two of the halides localized in mitochondrial membranes and colocalized with Pc 4 in these membranes. Their work also showed that microscopically observable FRET occurred between one of them and Pc 4 in MCF7-c3 cells.

Malcolm Kenney, E (Advisor)
John Protasiewicz, D (Committee Chair)
Nancy Oleinick, L (Committee Member)
Clemens Burda (Committee Member)
John Stuehr, E (Committee Member)
262 p.

Recommended Citations

Citations

  • Zhang, P. (2009). Synthesis and Characterization of New Silicon Phthalocyanines and Nonyl Acridine Orange Analogues for Photodynamic Therapy Studies [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1238098605

    APA Style (7th edition)

  • Zhang, Ping. Synthesis and Characterization of New Silicon Phthalocyanines and Nonyl Acridine Orange Analogues for Photodynamic Therapy Studies. 2009. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1238098605.

    MLA Style (8th edition)

  • Zhang, Ping. "Synthesis and Characterization of New Silicon Phthalocyanines and Nonyl Acridine Orange Analogues for Photodynamic Therapy Studies." Doctoral dissertation, Case Western Reserve University, 2009. http://rave.ohiolink.edu/etdc/view?acc_num=case1238098605

    Chicago Manual of Style (17th edition)