Abstract
Two new DTPA analogues, centrally (L1) and terminally (L2) functionalised with a 1,8-naphthalimide chromophore, have been successfully prepared and fully characterized.
Highlights
Diethylenetriaminepentaacetic acid (DTPA) is one of the most well-known ligands and yields highly stable complexes with hard metal ions
DTPA and its derivatives have been used in a vast array of applications of medical interest, such as contrast agents for medical imaging,[1,2,3,4,5] radiotherapy, radiolabeling of antibodies and peptides,[6,7,8,9] radiopharmaceuticals and chelation therapy.[10,11,12]
The gadolinium complex of DTPA has long been successful as a contrast agent, ever since it was approved by the FDA in 1988.13
Summary
Diethylenetriaminepentaacetic acid (DTPA) is one of the most well-known ligands and yields highly stable complexes with hard metal ions. DMF was added and the reaction mixture was gently heated to 65 C and stirred overnight. Yield 0.072 g, 84%; 1H NMR (400 MHz, D2O) dH (ppm) 8.00 (d, 2H, J 1⁄4 6.79 Hz), 7.92 (d, 2H, J 1⁄4 8.41 Hz), 7.40 (t, 2H, J 1⁄4 6.94 Hz), 3.7 (m, 4H), 3.40 (s, 8H), 2.90 (m, 4H), 2.80 (m, 4H); 13C NMR (400 Hz, D2O) dC 172.2, 168.7, 135.4, 135.6, 131.8, 131.6, 130.8, 127.1, 126.6, 119.9, 55.8, 55.3, 52.3, 50.8, 37.0; IR (KBr disc) (cmÀ1): 3430(br), 2963(w), 1695(s), 1655(vs), 1625(w), 1588(s); ESI-MS (Àion): found m/z 557.16, calc. A er the addition of DMF (20 ml), the reaction mixture was gently heated up to 65 C and allowed to stir overnight. The crude product was puri ed by ash chromatography the material (90 : 10 dichloromethane/methanol); the product was obtained from the eluents by evaporation of the solvent mixture. UV/vis [lmax, nm (3M, MÀ1 cmÀ1)] in H2O: 235(6752), 267(1679), 345(2309)
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