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Synthesis and characterization of macrocyclic compounds for photodynamic therapy and photothermal therapy

Posted on:2002-06-25Degree:Ph.DType:Dissertation
University:Case Western Reserve UniversityCandidate:Hao, GuolunFull Text:PDF
GTID:1464390011997832Subject:Chemistry
Abstract/Summary:
A group of twenty-six new phthalocyanine (MPc), phthalocyanine-like, naphthalocyanine (MNc), and anthralocyanine (MAc) complexes was synthesized and characterized for use in photodynamic therapy (PDT) structure-activity relationship (SAR) studies, photothermal therapy (PTT) SAR studies, and photophysical studies. Of these twenty-six, eleven are silicon phthalocyanines which were synthesized for PDT SAR studies. Two of these belong to a terminal-group set of homologues of SiPc[OSi(CH3)2(CH2) 3N(CH3)2]2, Pc 12, and one is related to this set. These are SiPc[OSi(CH3)2(CH2) 3N(n-C5H11)2] 2, Pc 113, SiPc[OSi(CH3)2(CH2) 3N(n-C6H13)2] 2, Pc 114, and SiPc[OSi(CH3)2(CH2) 3NH(CH3)]2, Pc 111. Four belong to a linker set of homologues of HOSiPcOSi(CH3)2(CH2) 3N(CH3)2, Pc 4; three to a terminal-group set of homologues of it; and one is related to this latter set. These are HOSiPcOSi(CH 3)2CH2N(CH3)2, Pc 115, HOSiPcOSi(CH 3)2(CH2)2N(CH3)2, Pc 116, HOSiPcOSi(CH3)2(CH2)5N(CH 3)2, Pc 117, HOSiPcOSi(CH3)2(CH 2)6N(CH3)2, Pc 118, HOSiPcOSi(CH 3)2(CH2)3N(n-C 3H7)2, Pc 121, HOSiPcOSi(CH3) 2(CH2)3N(n-C5H 11)2, Pc 122, HOSiPcOSi(CH3)2(CH 2)3N(n-C6H13) 2, Pc 123, and HOSiPcOSi(CH3)2(CH2) 3NH(CH3), Pc 119. Among the remaining fifteen compounds, three are octaethoxyphthalocyanines synthesized for PDT photochemical and photophysical studies. These are H2Pc(OEt)8, SiPc(OEt) 8(OH)2 and SiPc(OEt)8[OSi(CH3) 3]2. One is a silicon octabutoxyphthalocyanine prepared for PDT SAR studies. It is SiPc(OBu)8[OSi(CH3)2(CH 2)3N(CH3)2]2. Another is a zinc octabutoxynaphthalocyanine, ZnNc(OBu)8, made for PDT studies. Three are metal-free and silicon octabutoxyanthralocyanines prepared in support of PTT studies. These are H2Ac(OBu)8, SiAc(OBu) 8(OH)2 and SiAc(OBu)8[OSi(n-C 6H13)3]2. Three more are tin octabutoxyanthralocyanines prepared also to aid PTT studies. These are SnAc(OBu)8Cl2 , SnAc(OBu)8Br2 and SnAc(OBu)8I 2. The last four compounds are phthalocyanine-like compounds made for a study complementary to an NMR study of a previously made, similar naphthalocyanine-like group. These are H2A4−xPx(OBu) 8, where P represents a phthalocyanine-type arm in a phthalocyanine-like compound, and A represents an anthralocyanine-type arm, and x = 1–3. In addition, improved routes to the known silicon phthalocyanines, HOSiPcOSi(CH 3)2(CH2)3N(n-C 4H9)2, Pc 25, SiPc[OSi(CH3)2(CH 2)5N(CH3)2]2, Pc 84, and SiPc[O...
Keywords/Search Tags:Hosipcosi, SARstudies, Compounds, PDT, Obu, Silicon
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