Chinese Journal of Organic Chemistry >
Two Binuclear Nonionic Magnetic Resonance Contrast Agents with High Relaxivity
Received date: 2018-01-29
Revised date: 2018-03-04
Online published: 2018-03-29
Supported by
Project supported by the Natural Science Foundation in Jiangsu Province (No. 17KJB320001), the Top-notch Academic Programs Project of Jiangsu Higher Education Institutions (No. PPZY2015B179), the Training Program of Students Innovation and Entrepreneurship in Jiangsu Province (No. 201712920001Y), and the Qing Lan Project of Jiangsu Province.
Magnetic resonance imaging (MRI) is widely used in diagnostic medicine and soft tissue imaging. Contrast agents (CAs) can improve the specificity of MRI enhancement. Herein, the design, synthesis and relaxivity of two novel binuclear nonionic Gd-based DOTA-hydrazide derived MRI contrast agents, (Gd-DOTAH)2-DYMB and (Gd-DOTAH)2-DYMBP are reported. They have improved longitudinal relaxivity values of 11.4 and 11.7 L·mmol-1·s-1 per molecule or 5.7 and 5.9 L·mmol-1·Gd-1·s-1 at 0.5 T, respectively, which are higher than that of the mononuclear clinical macrocyclic agent Gd-DOTA. And in vitro MRI studies suggest the potential of these two agents as MRI contrast agents in improving the diagnostic sensitivity and accuracy.
Sun Hongshun , Li Yulong , Jiang Hong , Guo Cheng , Shen Linjiang . Two Binuclear Nonionic Magnetic Resonance Contrast Agents with High Relaxivity[J]. Chinese Journal of Organic Chemistry, 2018 , 38(7) : 1779 -1785 . DOI: 10.6023/cjoc201801044
[1] Caravan, P. ChemInform 2006, 35, 512.
[2] Wan, F.; Yu, K. Chin. J. Org. Chem. 2014, 34, 613 (in Chinese).
(万福贤, 俞开潮, 有机化学, 2014, 34, 613.)
[3] Hermann, P.; Kotek, J.; Kubícek, V.; Lukes, I. Dalton Trans. 2008, 23, 3027.
[4] Zhang, W.; Lu, C.; Zhao, G.; Zhang, J.; Fang, X.; Wang, P.; Fang, X.; Xu, J.; Yang, W. Z. Anorg. Allg. Chem. 2015, 641, 578.
[5] Pierre, V. C.; Allen, M. J.; Caravan, P. J. Biol. Inorg. Chem. 2014, 19, 127.
[6] Werner, E. J.; Datta, A.; Jocher, C. J.; Raymond, K. N. Angew. Chem., Int. Ed. 2008, 47, 8568.
[7] Lauffer, R. B. Chem. Rev. 1987, 87, 901.
[8] Caravan, P. Acc. Chem. Res. 2009, 42, 851.
[9] Hermann, P.; Kotek, J.; Kubicek, V.; Lukes, I. Dalton Trans. 2008, 3027.
[10] Supkowski, R. M.; Horrocks, W. D. Inorg. Chem. 1999, 38, 5616.
[11] Laurent, S.; Vander Elst, L.; Muller, R. N. Contrast Media Mol. Imaging 2006, 1, 128.
[12] Yang, J.-J.; Yang, J.; Wei, L.; Zurkiya, O.; Yang, W.; Li, S.; Zou, J.; Zhou, Y.; Maniccia, A. L. W.; Mao, H.; Zhao, F.; Malchow, R.; Zhao, S.; Johnson, J.; Hu, X.; Krogstad, E.; Liu, Z.-R. J. Am. Chem. Soc. 2008, 130, 9260.
[13] Huang, C. H.; Tsourkas, A. Curr. Top. Med. Chem. 2013, 13, 411.
[14] Ye, Z.; Wu, X.; Tan, M.; Jesberger, J.; Grisworld, M.; Lu, Z.-R. Contrast Media Mol. Imaging 2013, 8, 220.
[15] Aime, S.; Caravan, P. J. Magn. Reson. Imaging 2009, 30, 1259.
[16] Livramento, J. B.; Sour, A.; Borel, A.; Merbach, A. E.; Tóth, É. Chem.-Eur. J. 2006, 12, 989.
[17] Li, W.-S.; Luo, J.; Jiang, F.; Chen, Z.-N. Dalton Trans. 2012, 41, 9405.
[18] Luo, J.; Li, W.-S.; Xu, P.; Zhang, L.-Y.; Chen, Z.-N. Inorg. Chem. 2012, 51, 9508.
[19] Zhao, G.; Lu, C.; Li, H.; Xiao, Y.; Zhang, W.; Fang, X.; Wang, P.; Fang, X.; Xu, J.; Yang, W. Inorg. Chim. Acta 2013, 406, 146.
[20] Zhao, G.; Li, H.; Lu, C.; Xiao, Y.; Fang, X.; Wang, P.; Fang, X.; Zhao, K.; Li, X.; Yin, S.; Xu, J.; Yang, W. RSC Adv. 2012, 2, 6404.
[21] He, W.; Oliver, T. B.; Michael, G. K.; Eric, C. H.; Mariya, B.; Agata, W.; Ou, C.; Yue, C.; Nan, L.; Satoshi, O.; Jose, M. C.; Markus, H.; Christian, T. F.; Daniel, M. M.; Gerhard, A.; Harald, I.; Alan, J.; Peter, N.; Moungi, G. B. Proc. Natl. Acad. Sci. U. S. A. 2017, 114, 2325.
[22] Huckle, J. E.; Altun, E.; Jay, M. J.; Semelka, R. C. Invest. Radiol. 2016, 51, 236.
[23] Boros, E.; Gale, E. M.; Caravan, P. Dalton Trans. 2015, 44, 4804.
[24] Frullano, L.; Tejerina, B.; Meade, T. J. Inorg. Chem. 2006, 45, 8489.
[25] Fuge, F.; Weiler, M.; Gätjens, J.; Lammers, T.; Kiessling, F. Tetrahedron Lett. 2013, 54, 918.
[26] Cresens, E.; Ni, Y.-C.; Adriaens, P.; Verbruggen, A.; Marchal, G. WO 2002038546, 2002[Chem. Abstr. 2002, 136, 379071].
[27] Zhang, J.-D.; Curry, K. WO 2016090491, 2016 [Chem. Abstr. 2016, 165, 112684].
[28] Mieville, P.; Jaccard, H.; Reviriego, F.; Tripier, R.; Helm, L. Dalton Trans. 2011, 40, 4260.
[29] Jagadish, B.; Brickertalbrecht, G. L.; Nichol, G. S.; Mash, E. A.; Raghunand, N. Tetrahedron Lett. 2011, 52, 2058.
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