Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (4): 613-629.DOI: 10.6023/cjoc201310052 Previous Articles Next Articles
Reviews
万福贤a, 俞开潮b
收稿日期:2013-10-31
修回日期:2013-12-18
发布日期:2013-12-27
通讯作者:
俞开潮
E-mail:yukc@163.com
基金资助:国家自然科学基金（No. 20675033）和山东省科技发展计划（No. 2013CEX2019）资助项目
Wan Fuxiana, Yu Kaichaob
Received:2013-10-31
Revised:2013-12-18
Published:2013-12-27
Supported by:Project supported by the National Natural Science Foundation of China (No. 20675033) and the Science and Technology Development of Shandong Province (No. 2013CEX2019).
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Wan Fuxian, Yu Kaichao. Recent Progress in the Synthesis of Bifunctional Diethylenetriamine-pentaacetic Acid Derivatives Ligand for Magnetic Resonance Imaging Contrast Agent[J]. Chin. J. Org. Chem., 2014, 34(4): 613-629.
| [1] Lauterbur, P. C. Nature 1973, 242, 190.[2] Zhou, Z.; Wu, X.; Kresak, A.; Griswold, M.; Lu, Z.-R. Biomaterials 2013, 34, 7683.[3] Caravan, P.; Ellison, J. J.; McMurry, T. J.; Lauffer, R. B. Chem. Rev. 1999, 99, 2293.[4] Gallez, B.; Swartz, H. M. NMR Biomed. 2004, 17, 223.[5] Alper, J. Science 1993, 261, 554.[6] Sipkins, D. A.; Cheresh, D. A.; Kazemi, M. R.; Levin, L. M.; Bednarski, M. D.; Li, K. C. Nat. Med. 1998, 4, 623.[7] Liang, S.-B.; Chang, F.; Li, J.-Q.; Li, X.-X.; Song, C.-M. Polym. Bull. 2011, 7, 96 (in Chinese)(梁晟斌, 常飞, 李建奇, 李欣欣, 宋春梅, 高分子通报, 2011, 7, 96.)[8] Tang, J.; Sheng, Y.; Hu, H.; Shen, Y. Prog. Polym. Sci. 2013, 38, 462.[9] Yu, K.-C.; Lv, Z.-R.; Yao, Y.; Fu, S.-T.; Ding, S.-W.; Zhou, J.-L. Chin. J. Magn. Reson. 2010, 27, 355 (in Chinese).(俞开潮, 吕志勇, 姚遥, 付世涛, 丁尚武, 周锦兰, 波谱学杂志, 2010, 27, 355.)[10] Accardo, A.; Tesauro, D.; Aloj, L.; Pedone, C.; Morelli, G. Coord. Chem. Rev. 2009, 253, 2193.[11] Zhang, S.-R.; Ren, J.-M.; Pei, F.-K. Prog. Chem. 1995, 7, 98 (in Chinese).(张善荣, 任吉民, 裴奉奎, 化学进展, 1995, 7, 98.)[12] Yan, G.-P.; Zhuo, R.-X. Chin. Sci. Bull. 2001, 46, 1233 (in Chinese)(鄢国平, 卓仁禧, 科学通报, 2001, 46, 1233.)[13] Yan, G. P.; Robinson, L.; Hogg, P. Radiography 2007, 13, 5.[14] Frullano, L.; Caravan, P. Curr. Org. Synth. 2011, 8, 535.[15] Caravan, P. Chem. Soc. Rev. 2006, 35, 512.[16] Weinmann, H. J.; Brash, R. C.; Press, W. R.; Wesbey, G. E. Am. J. Radiol. 1984, 142, 619.[17] Cacheris, W. P.; Nickle, S. K.; Sherry, A. D. Inorg. Chem. 1987, 26, 958.[18] Brucher, E. Top. Curr. Chem. 2002, 221, 103.[19] Toth, E.; Brucher, E.; Lazar, I.; Toth, I. Inorg. Chem. 1994, 33, 4070.[20] Sarka, L.; Burai, L.; Brucher, E. Chem. Eur. J. 2000, 6, 719.[21] Laurent, S.; Vander, L.; Copoix, F.; Muller, R. N. Invest. Radiol. 2001, 36, 115.[22] Marckmann, P.; Skov, L.; Rossen, K. J. Am. Soc. Nephrol. 2006, 17, 2359.[23] High, W. A.; Ayers, R. A.; Chandler, J.; Zito, G.; Cowper, S. E. J. Am. Acad. Dermatol. 2007, 56, 21.[24] Shellock, F. G.; Spinazzi, A. Am. J. Roentgenol. 2008, 191, 1.[25] Feng, J. H.; Sun, G.Y.; Pei, F.K.; Liu, M. L. J. Inorg. Biochem. 2002, 92, 193.[26] Yang, X.-L.; Yang, X. -W.; Huang, Y.; Zhang, Q.;Wu, J.-B.; Cao, B.-N.; Zhang, X.-Y. Chem. J. Chin. Univ. 2012, 33, 426 (in Chinese)(杨晓露, 杨兴旺, 黄燕, 张岐, 吴静波, 曹本南, 张晓燕, 高等学校化学学报, 2012, 33, 426.)[27] Zhou, X.; Yang, L.; Yan, G. P.; Xu, W.; Zhou, C. K.; Zhang, Q.; Li, L.; Liu, F.; Guo, J. F.; Zhao, Q. J. Rare Earths 2012, 30, 884.[28] Park, J.-A.; Kim, H.-K.; Kim, J.-H.; Jeong, S.-W.; Jung, J.-C.; Lee, G.-H.; Lee, J.; Chang, Y.; Kim, T.-J. Bioorg. Med. Chem. Lett. 2010, 20, 2287.[29] Sankar, A. U. R.; Yamasitha, M.; Srinivasulu, K.; Ozaki, N.; Aoki, T.; Fujie, M.; Ogawa, K.; Okada, S.; Yamada, M.; Tanaka, Y.; Kimura, M.; Toda, M. Tetrahedron Lett. 2010, 51, 2431.[30] Ozaki, N.; Sankar, A. U. R.; Yamasitha, M.; Aoki, T.; Tanaka, Y.; Kimura, M.; Toda, M.; Fujie, M.; Takehara, Y.; Sakahara, H. Bioorg. Med. Chem. Lett. 2010, 20, 932.[31] Zhao, X.; Zhuo, R. X.; Lu, Z. R. Polyhedron 1997, 16, 2755.[32] Yu, K.-C.; Hu, H.-B.; Liu, M.-L.; Yuan, H.-Z.; Ye, Z.-H.; Zhou, R.-X. Chin. J. Polym. Sci. 1999, 17, 471.[33] Yu, K.-C.; Wang, X.-B.; Ye, C.-H.; Li, L.-Y.; Liu, M.-L.; Zhuo, R.-X. Chin. J. Chem. 2001, 19, 788.[34] Yu, K.-C.; Wang, X.-B.; Li, L.-Y.; Ye, C.-H. Prog. Nat. Sci. 1999, 9, 1036 (in Chinese) (俞开潮, 王新兵, 李丽云, 叶朝辉, 自然科学进展, 1999, 9, 1036.)[35] Yu, K.-C.; Feng, J.-W.; Hu, H.-B.; Lu, G.; Zhuo, R.-X.; Li, L.-Y.; Ye, C.-H. Chin. J. Magn. Reson. 1998, 15, 123 (in Chinese).(俞开潮, 冯继文, 胡红兵, 卢广, 卓仁禧, 李丽云, 叶朝辉, 波谱学杂志, 1998, 15, 123.)[36] Tang, H.A.; Yang, S.; Yang, R. D. Synth. Commun. 2003, 33, 2811.[37] Wei, J.-F.; Zhuo, R.-X.; He, D.-P. J. Rare Earths 1999, 17, 166.[38] Fu, Y.-J.; Zhuo, R.-X. Chem. J. Chin. Univ. 1997, 18, 1072 (in Chinese).(傅雁军, 卓仁禧, 高等学校化学学报, 1997, 18, 1072.)[39] Yan, G.-P.; Zhuo, R.-X.; Xu, M.-P.; Li, L.-Y.; Tang, Y.-F. Sci. China: Chem. 2001, 31, 253 (in Chinese).(郡国平, 卓仁禧, 徐勉彭, 李丽云, 唐岳枫, 中国科学(B辑), 2001, 31, 253.)[40] Lee, T.-M.; Cheng, T.-H.; Ou, M.-H.; Chang, C.-A.; Wang, Y.-M. Magn. Reson. Chem. 2004, 42, 329.[41] Richard, C.; Chaumet-Riffaud, P.; Belland, A.; Parat, A.; Contino-Pepin, C.; Bessodes, M.; Scherman, D.; Pucci, B.; Migent, N. Int. J. Pharm. 2009, 379, 301.[42] Yu, K.-C.; Wan, F.-X.; Zhang, Y.; Zhou, J.-L.; Lu, G.; Liu, M.-L.; Ding, S.-W. Chin. J. Inorg. Chem. 2004, 20, 389 (in Chinese).(俞开潮, 万福贤, 张焱, 周锦兰, 卢广, 刘买利, 丁尚武, 无机化学学报, 2004, 20, 389.)[43] Yu, K. C.; Hamdan, Y.; Wan, F. X.; Li, Y. X.; Huang, K. X.; Zhou, J. L. Aust. J. Chem. 2007, 60, 218.[44] Yu, K.-C.; Li, L. Y.; Wan, F.-X.; Zhou, J.-L.; Ding, S.-W.; Ye, C.-H. Spectrosc. Spectral Anal. 2006, 26, 670 (in Chinese).(俞开潮, 李留义, 万福贤, 周锦兰, 丁尚武, 叶朝辉, 光谱学与光谱分析, 2006, 26, 670.)[45] Zhou, J.-L.; Wan, F.-X.; Yu, K.-C.; Ding, S.-W. Chem. J. Chin. Univ. 2005, 26, 1391 (in Chinese).(周锦兰, 万福贤, 俞开潮, 丁尚武, 高等学校化学学报, 2005, 26, 1391.)[46] Yu, K. C.; Li, Y. X.; Zhou, J. L.; Ding, S. W.; Ye, C. H. Chem. Res. Chin. Univ. 2005, 21, 512.[47] Zhou, J.-L.; Wan, F.-X.; Yu, K.-C.; Ding, S.-W.; Yang, N.-H.; Ye, C.-H. Chin. J. Inorg. Chem. 2005, 21, 1237 (in Chinese).(周锦兰, 万福贤, 俞开潮, 丁尚武, 杨年华, 叶朝辉, 无机化学学报, 2005, 21, 1237.)[48] Halpern, S.; Stern, P.; Hagan, P.; Chen, A.; Frincke, J.; Bartholomew, R.; David, G.; Adams, T. In Radioimmunoimaging and Radioimmunotherapy, Eds.: Burchiel, E. W.; Rhodes, B. A., Elsevier, New York, 1983, p. 197.[49] Subramanian, R. WO 9014881, 1991 [Chem. Abstr. 1991, 115, 91839].[50] Ratanajanchai, M.; Lee, D. H.; Sunintaboon, P.; Yang, S.-G. J. Colloid Interface Sci. 2014, 415, 70.[51] Yuan, J.; Miao, C.; Peng, F.; Zeng, X.; Guo, H.; Wang, X.; Li, S.; Xie, X. J. Appl. Polym. Sci. 2013, 127, 4549.[52] Yang, Z.-Z.; Ding, C.-X.; Qu, X.-Z.; Liu, J.-G. CN 101307018, 2008 [Chem. Abstr. 2008, 150, 36045].[53] Alleti, R.; Vagner, J.; Dehigaspitiya, D. C.; Moberg, V. E.; Elshan, N. G. R. D.; Tafreshi, N. K.; Brabez, N.; Weber, C. S.; Lynch, R. M.; Hruby, V. J.; Gillies, R. J.; Morse, D. L.; Mash, E. A. Bioorg. Med. Chem. 2013, 21, 5029.[54] Jiang, X.-M. M.S. Thesis, Huazhong University of Science and Technology, Wuhan, 2005 (in Chinese).(江湘梅, 硕士论文, 华中科技大学, 武汉, 2005.)[55] Enginar, H.; Unak, P.; Lambrecht, F. Y.; Muftuler, F. Z. B.; Medine, E. I. In Vivo 2008, 22, 93.[56] Ardestani, M. S.; Arabzadeh, A. J.; Heidari, Z.; Hosseinzadeh, A.; Ebrahimi, H.; Hashemi, E.; Mosayebina, M.; Ebrahimi, S. E. S.; Amanlou, M. J. Radioanal. Nucl. Chem. 2010, 283, 447.[57] Arano, Y.; Uezono, T.; Akizawa, H.; Ono, M.; Wakisaka, K.; Nakayama, M.; Sakahara, H.; Konishi, J.; Yokoyama, A. J. Med. Chem. 1996, 39, 3451.[58] Leclercq, F.; Cohen-Ohana, M.; Mignet, N.; Sbarbati, A.; Herscovici, J.; Scherman, D.; Byk, G. Bioconjugate Chem. 2003, 14, 112.[59] Felder, E.; Anelli, P. L.; Virtuani, M.; Beltrami, A.; Lolli, M. WO 9515319, 1995 [Chem. Abstr. 1995, 123, 357595].[60] Roy, B. C.; Mallik, S. Org. Lett. 2001, 3, 1877.[61] Lee, T.-W.; Yang, C.-H.; Ho, Y.-S.; Lu, L.-H.; Chen, S.-L. US 7767844, 2010 [Chem. Abstr. 2006, 145, 505757].[62] Burks, E.; Koshti, N.; Jacobs, H.; Gopalan, A. Synlett 1998, 1285.[63] Giordano, C.; del Bianco, C.; Faini, S.; Napoli, A.; Sindona, G.; Cellai, L. Synthesis 2004, 1835.[64] Davies, J. S.; Al-Jamri, L. J. Pept. Sci. 2002, 8, 663.[65] Steve, P. R.; Nicola, J. D. Org. Lett. 2000, 14, 2117.[66] Lv, Z.-Y. M.S. Thesis, Huazhong University of Science and Technology, Wuhan, 2011 (in Chinese).(吕志勇, 硕士论文, 华中科技大学, 武汉, 2011.)[67] Anelli, P. L.; Fedeli, F.; Gazzotti, O.; Lattuada, L.; Lux, G.; Rebasti, F. Bioconjugate Chem. 1999, 10, 137.[68] McMurry, T. J.; Pippin, C. G.; Wu, C.; Deal, K. A.; Brechbiel, M. W.; Mirzadeh, S.; Gansow, O. A. J. Med. Chem. 1998, 41, 3546.[69] Brechbiel, M. W.; Gansow, O. A.; Atcher, R. W.; Schlom, J.; Esteban, J.; Simpson, D.; Colcher, D. Inorg. Chem. 1986, 25, 2772.[70] Brechbiel, M. W.; Gansow, O. A. Bioconjugate Chem. 1991, 2, 187.[71] Cummins, C. H.; Rutter, E. W. Jr.; Fordyce, W. A. A. Bioconjugate Chem. 1991, 2, 180.[72] Corson, D. T.; Meares, C. F. Bioconjugate Chem. 2000, 11, 300.[73] Schmitt-Willich, H.; Brehm, M.; Ewers, C. L. J.; Michl, G.; Mueller-Fahrnow, A.; Petrov, O.; Platzek, J.; Raduechel, B.; Suelzle, D. Inorg. Chem. 1999, 38, 1134.[74] Mindt, T. L.; Müller, C.; Stuker, F.; Salazar, J.-F.; Hohn, A.; Mueggler, T.; Rudin, M.; Schibli, R. A. Bioconjugate Chem. 2009, 20, 1940.[75] Sajiki, H.; Ong, K. Y.; Nadler, S. T.; Wages, H. E.; McMurry, T. J. Synth. Commun. 1996, 26, 2511.[76] Amedio, J. C..; Bernard, P. J.; Fountain, M.; Wagenen, V. G. Synth. Commun. 1999, 29, 2377.[77] Cox, J. P. L.; Craig, A. S.; Helps, I. M.; Jankowski, K. J.; Parker, D.; Eaton, M. A. W.; Millican, A. T.; Millar, K.; Beeley, N. R. A.; Boyce, B. A. J. Chem. Soc., Perkin Trans. 1 1990, 2567.[78] Anelli, P. L.; Lattuada, L.; Lorusso, V.; Lux, G.; Morisetti, A.; Morosini, P.; Serleti, M.; Uggeri, F. J. Med. Chem. 2004, 47, 3629.[79] Uggeri, F.; Aime, S.; Anelli, P. L.; Botta, M.; Brocchetta, M.; de Haeen, C.; Ermondi, G.; Grandi, M.; Paoli, P. N. Inorg. Chem. 1995, 34, 633.[80] Westerberg, D. A.; Carney, P. L.; Rogers, P. E.; Kline, S. J.; Johnson, D. K. J. Med. Chem. 1989, 32, 236.[81] Li, J. F.; Huang, S. X.; Shao, K.; Liu, Y.; An, S.; Kuang, Y. Y.; Guo, Y. B.; Ma, H. J.; Wang, X. X.; Jiang, C. Sci. Rep. 2013, 3, 1623.[82] Keana, J. F. W.; Mann, J. S. J. Org. Chem. 1990, 55, 2868.[83] Williams, M. A.; Rapoport, H. J. Org. Chem.1993, 58, 1151.[84] Anelli, P. L.; Fedeli, F.; Gazzotti, O.; Lattuada, L.; Lux, G.; Rebasti, F. Bioconjugate Chem. 1999, 10, 137.[85] Luo, K.; Liu, G.; She, W. C.; Wang, Q. Y.; Wang, G.; He, B.; Ai, H.; Gong, Q. Y.; Song, B.; Gu, Z. W. Biomaterials 2011, 32, 7951.[86] She, W.-C.; Luo, K.; He, B.; Ai, H.; Gu, Z.-W. Acta. Polym. Sin. 2011, (2), 157 (in Chinese).(佘汶川, 罗奎, 何斌, 艾华, 顾忠伟, 高分子学报, 2011, (2), 157.)[87] Lattuada, L.; Gabellini, M. Synth. Commun. 2005, 35, 2049.[88] Lee, S.-Y.; Hong Y. D.; Kim, H.-S.; Choi, S.-J. Nucl. Med. Biol. 2013, 40, 424. |
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