The main focus of this thesis is finding methods by which a long-wavelength absorbing porphyrin isomer, 2,7,12,17-tetra-n-propylporphycene TPPc, can be functionalized to provide potentially useful drugs for photodynamic therapy....[ Read more ]

The main focus of this thesis is finding methods by which a long-wavelength absorbing porphyrin isomer, 2,7,12,17-tetra-n-propylporphycene TPPc, can be functionalized to provide potentially useful drugs for photodynamic therapy.

TPPc sulfonamides were synthesized in high yields by treating TPPc with neat chlorosulfonic acid, followed by reaction with primary or secondary amines. The sulfonamides could be further treated with methyl iodide to obtain the TPPc quaternary ammonium salts which prove to show very high phototoxicity. The most interesting derivative 2,7,12,17- tetra- n- propylporphycene sulfonyl- N,N’,N’,N’- tetramethylhexa- 1,6-diamine quaternary ammonium salt (PS6A) was studied in detail to understand its activities.

The formation of singly iodinated TPPc was completed by iodine monochloride, which undergoes various coupling reactions, including Suzuki coupling reaction, amine coupling reaction and Heck reaction. 3-iodo-TPPc was characterized by ¹H NMR and x-ray crystallography.

TPPc with functional group at bridge positions were obtained by nitration and acetoxylation. Tetra-substitution was observed by treating TPPc with an excess of lead(IV) tetraacetate to give 9,10,19,20-tetraacetoxy-TPPc.

These compounds were synthesized in reasonable yields and well characterized. Their potential applications in PDT have been demonstrated by testing on in vital nasopharyngeal cancer cell lines.