Phthalocyanine photosensitizers for photodynamic therapy and methods for their use
AssigneeUniversity Hospitals of Cleveland
InventorsMalcolm E. Kenney, Nancy L. Oleinick, Boris D. Rihter, Ying-Syi Li
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Abstract
The present invention relates to a series of novel phthalocyanine compositions (or compounds) suitable for use as photosensitizers for photodynamic therapy. Specifically, the invention relates to a series of new aluminum (Al) germanium (Ge), gallium (Ga), tin (Sn) and/or silicon (Si) phthalocyanines having substituted amine or quaternary ammonium axial ligands attached to the central metal, and the use of these new phthalocyanine compositions for the treatment of cancer through photosensitization. Moreover, the present invention is directed to the methods of preparing these compositions for use in photodynamic therapy.
Claims35
A phthalocyanine compound having the following formula:
- ##STR3## wherein M is (G).sub.a Y [(OSi(CH.sub.3).sub.2 (CH.sub.2).sub.b N.sub.c (R').sub.d (R").sub.e).sub.f X.sub.g ].sub.p wherein:
- Y is selected from the group consisting of Si, Al, Ga, Ge, and Sn;
- R' is selected from the group consisting of H, CH.sub.2, CH.sub.3, C.sub.2 H.sub.5, C.sub.4 H.sub.9, C.sub.4 H.sub.8 NH, C.sub.4 H.sub.8 NCH.sub.3, C.sub.4 H.sub.8 S, C.sub.4 H.sub.8 O, C.sub.4 H.sub.8 Se, CH.sub.2 CH.sub.3, (CH.sub.2).sub.3 (CH.sub.3), OC(O)CH.sub.3, CS, CO, CSe, OH, C.sub.4 H.sub.8 N(CH.sub.2).sub.3 CH.sub.3, (CH.sub.2).sub.3 N(CH.sub.3).sub.2, C(O)C.sub.27 H.sub.30 N.sub.2 O, (CH.sub.2).sub.n N((CH.sub.2).sub.o (CH.sub.3)).sub.2, and an alkyl group having from 1 to 12 carbon atoms;
- R" is selected from the group consisting of H, SO.sub.2 CH.sub.3, (CH.sub.2).sub.2 N(CH.sub.3).sub.2, (CH.sub.2).sub.11 CH.sub.3, C(S)NHC.sub.6 H.sub.11 O.sub.5, (CH.sub.2).sub.n N((CH.sub.2).sub.o (CH.sub.3)).sub.2, and an alkyl group having from 1 to 12 carbon atoms;
- G is selected from the group consisting of OH, CH.sub.3, and (CH.sub.3).sub.3 C(CH.sub.3).sub.2 SiO;
- X is selected from the group consisting of:
- I;
- F;
- Cl;
- and Br;
- a=0 where Y is Al or Ga, or 1 where Y is Si, Ge, or Sn;
- b=an integer from 2 to 12;
- c=0 or 1;
- d=0, 1, 2 or 3;
- e=0, 1, or 2;
- f=1 or 2;
- g=0 or 1;
- n=an integer from 1 to 12;
- o=an integer from 1 to 11;
- and
- p=1 or 2;
- where M is not AlOSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.2 ;
- AlOSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.3.sup.+ I.sup.- ;
- CH.sub.3 SiOSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.2 ;
- HOSiOSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.2 ;
- HOSiOSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.3.sup.+ I.sup.- ;
- Si[OSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.3.sup.+ I.sup.- ].sub.2 ;
- or Si[OSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.2 ].sub.2.
A phthalocyanine compound having the following formula SiPc[OSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.2 ].sub.2.
A method for treating fibrosarcomas, squamous cell carcinoma and skin tumors comprising the steps of administering an effective amount of a phthalocyanine wherein the phthalocyanine is HOSiPcOSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.2, and applying light of sufficient wave length and intensity to the fibrosarcoma, squamous cell carcinoma or skin tumor to activate said phthalocyanine, wherein said activated phthalocyanine exerts a cytotoxic effect on said fibrosarcoma, squamous cell carcinoma or skin tumor.
A method for treating fibrosarcomas, squamous cell carcinoma, and skin tumors comprising the steps of administering, to a patient, an effective amount of a phthalocyanine, and applying light of sufficient wave length and intensity tot he fibrosarcoma, squamous cell carcinoma or skin tumor to activate said phthalocyanine, wherein said activated phthalocyanine exerts a cytotoxic effect on said fibrosarcoma, squamous cell carcinoma or skin tumor and
- wherein said phathalocyanine is SiPc[OSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.2 ].sub.2.
A phthalocyanine compound having the following formula:
- CH.sub.3 SiPcOSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.2.
A phthalocyanine compound having the following formula:
- SiPc[OSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.3.sup.+ I.sup.- ].sub.2.
Dependencies are inferred from the claim text.