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Proteomic characterization of the cytotoxic mechanism of gold (III) porphyrin 1a, a potential anticancer drug

“…In the past few decades considerable effort has been devoted to the search for new chemotherapeutic agents with preferential anticancer activity. However, although there have been important developments in the field of anticancer che-motherapy, no breakthrough has been achieved in the search for better anticancer agents since the introduction of cis-diamminedichloro-platinum (II) (cisplatin) into clinical use [1,2]. In recent years research has increasingly focused on the potential of gold (III) complexes as anticancer drug candidates, because gold (III) possesses the same isoelectronic configuration (d 8 ) and structural (square planar) characteristics as platinum (II) [3][4][5].…”

Synthesis and Cancer Cell Cytotoxicity of Gold(III) Tetraarylporphyrins with a C5-Carboxylate Substituent

“…Zeisel reaction of triaryl(4-methoxyphenyl) porphyrins (1)(2)(3) with BBr 3 at room temperature for 2 h afforded triaryl(4-hydroxyphenyl) porphyrins (5-7) (90-94% in yield) (Scheme 1, Table 1). Hydrolysis of 5,10,15-tri(4-methoxyphenyl)-20-(4-acetoxylphenyl) porphyrin (4) in the presence of sodium hydroxide at room temperature for 12 h gave 5,10,15-tri(4-methoxyphenyl)-20-(4-hydroxyphenyl) porphyrin (8) in 85% yield (Scheme 1, Table 1).…”

Gold(III) Tetraarylporphyrin Phosphonate Derivatives as Potential Anticancer Agents

“…After removal of solvent, the crude product was purified by column chromatography (silica gel, CH 2 Cl 2 /n-hexane/Et 3 N: 1/1/0.01 V/V/V) to give the title compound 5a in 78.0% yield(15.5 mg). 1 (15 mL) was refluxed for 18-24 h. After completion, the reaction was checked by TLC, the crude product was obtained by removing acetic acid. Next, the solid product was dissolved thoroughly with dichloromethane (20 mL) and the organic phase was washed thoroughly with water and brine respectively, and then dried over Na 2 SO 4 .…”

“…The purified product was dissolved in acetone and after filtering the mixture, the solution was treated with 10% LiCl (3.5 mL) in aqueous acetone to give analytically pure 6a in 70.5% yield (16.9 mg) as a purple-mahogany solid. 1 and DMSO solvent were set up at the same time. The cytotoxicities of gold(III) substituted tetraarylporphyrin chlorides were determined by MTT cytotoxic assay.…”

“…]phenyl-10,15,20-triphenylporphyrin (5b): Following the above procedure using diethyl phosphonate as the starting material, 5b was obtained as a purple solid (56.5% yield): 1 H NMR (CDCl 3 , 600 MHz) δ (ppm)]phenyl-10,15,20-triphenylporphyrin (5c): Following the above procedure using diisopropyl phosphonate as the starting material, compound 5c was obtained as a purple solid(58.9% yield):1 H NMR (CDCl 3 , 600 MHz) δ (ppm): 8.87-8.85 (m, 8H), 8.23 (d, J = 6.6 Hz, 6H), 8.10 (d, J = 7.8 Hz, 2H), 7.79-7.75 (m, 9H), 7.36 (d, J = 8.4 Hz, 2H), 5.44 (d, J = 7.8 Hz, 1H), 4.09-4.08 (m, 1H), 3.95-3.89 (m, 1H), 1.46 (d, J = 6.0 Hz, 12H), -2.73 (s, 2H); MS (EI): 794.44 (M+1, 100%); IR (KBr, cm −1 ): 3315, 2921, 2850, 1596, 1467, 1399, 1308, 1223, 1153, 990, 964, 873, 752; UV-Vis (CH 2 Cl 2 ) λ max/ nm (log ε) 425 (2.12), 522 (1.41), 554 (2.90), 592 (4.85), 640 (4.09); Anal. Calcd for C 50 H 44 N 5 O 3 P: C, 75.64; H, 5.59; N, 8.82.…”