Vascular targeting of bacteriochlorin photodynamic therapy of cancer

Guanidine and Biguanidine Derivatives of Natural Chlorins: Synthesis and Biological Assessment

“…In the other two methods used, the composition of solvents, temperature conditions and reaction times were changed (Table 1), while the amounts of the starting compound 1, ethyldiisopropylamine and pyrazole-1H-carboxyamidine were the same. 1 H NMR (300 MHz, CDСl 3 ) δ H ppm: 9.68 (Н, s, 10-Н), 9.63 (Н, s, 5-Н), 9.41 (3H, br.s, 13 9 -NH 2 , 13 10 -NH), 8.81 (Н, s, 20-Н), 8.07 (H, dd, J = 17.8 Hz, 11.5 Hz, 3 1 -Н), 7.40 (Н, m, 13 7 -NH) 6.98 (H, t, J = 5.2 Hz, 13 2 -NH), 6.33 (H, dd, J = 17.8 Hz,1.4 Hz, Е-3 2 -Н), 6.11 (Н, dd, J = 11.5 Hz, 1.4 Hz, Z-3 2 -Н), 5.55 (Н, d, J = 18.9 Hz, 15-СН 2 а ), 5.25 (Н, d, J = 18.9 Hz, 15-СН 2 b ), 4.47 (Н, m, 18-Н), 4.35 (Н, m, 17-Н), 3.80 (2H, m, 8 1 -СН 2 ), 3.79 (3Н, s, 15 2 -СОOСН 3 ), 3.61 (3Н, s, 12 1 -СН 3 ), 3.54 (3Н, s, 17 3 -СОOСН 3 ), 3.49 (3Н, s, 2 1 -СН 3 ), 3.48 (2H, m, 13 3 -CH 2 ), 3.30 (3Н, s, 7 1 -СН 3 ), 2.78 (2Н, m, 13 6…”

“…The reaction was performed for 15 minutes with heating at 140 °C, with vigorous stirring and irradiation with adjustable power in the range of 0-400 W, at 2.45 GHz using a Biotage ® Initiator 2.0 microwave reactor. After the reaction products were isolated by extrac- H NMR (300 MHz, CDСl 3 ) δ H ppm: 9.69 (Н, s, 10-Н), 9.61 (Н, s, 5-Н), 9.41 (3H, br.s, 13 9 -NH 2 , 13 10 -NH), 8.83 (Н, s, 20-Н), 8.26 (3Н, br.s, 13 12 -NH, 13 13 -NH 2 ) 8.07 (H, dd, J = 17.8 Hz, 11.5 Hz, 3 1 -Н), 7.40 (Н, m, 13 7 -NH) 6.95 (H, t, J = 5.2 Hz, 13 2 -NH), 6.3 (H, dd, J = 17.8 Hz,1.4 Hz, Е-3 2 -Н), 6.11 (Н, dd, J = 11.5 Hz, 1.4 Hz, Z-3 2 -Н), 5.55 (Н, d, J = 18.9 Hz, 15-СН 2 а ), 5.25 (Н, d, J = 18.9 Hz, 15-СН 2 b ), 4.41 (Н, m, 18-Н), 4.35 (Н, m, 17-Н), 3.83 (2H, m, 8 1 -СН 2 ), 3.78 (3Н, s, 15 2 -СОOСН 3 ), 3.6 (3Н, s, 12 1 -СН 3 ), 3.54 (3Н, s, 17 3 -СОOСН 3 ), 3.49 (3Н, s, 2 1 -СН 3 ), 3.48 (2H, m, 13 3 -CH 2 ), 3.30 (3Н, s, 7 1 -СН 3 ), 2.75 (2Н, m, 13 6 ), 1.73 (3H, d, J = 7.1 Hz, 18-CH 3 ), 1.62 (3H, t, J = 7.6 Hz, 8 2 -СН 3 ), 1.28 (4H, m, 13 4 -13 5 -СН 2 ), -1.61 (Н, br.s, I-NH), -1.83 (Н, br.s, III-NH). 13…”

“…The accumulation of chlorins in tumor vessels or internalization into cancer cells largely depends on the structure of pigments. For example, bacteriochlorins tend to be accumulated in the endothelium of tumor vessels, [3] whereas chlorophyll a derivatives may be accumulated in certain compartments of tumor cells without penetration into their nuclei, depending on the nature and charge of substituents on the macrocycle periphery. [4][5][6] Compounds containing guanidine and biguanidine groups are widespread in nature and participate in many biochemical processes in cells.…”