基于大环合成受体的超分子纳米阀门

doi:10.3969/j.issn.0251-0790.2012.08.001

摘要/Abstract

摘要： 在特定外界刺激下, 修饰于介孔纳米材料表面的超分子纳米阀门可以有效地控制所包封物质如药物模型分子、抗癌药物分子和寡核酸等生物分子的靶向释放, 在药物释放、基因转染及传感等领域有广泛的应用前景. 本文结合本课题组的工作, 综述了国内外在基于大环合成受体的超分子纳米阀门体系的化学构筑及功能等方面的研究进展.

关键词: 纳米阀门, 超分子化学, 大环合成受体, 主客体化学

Abstract: Supramolecular nanovalves, installed on the surface of mesoporous nanomaterials, could effectively control the targeted release of encapsulated cargo molecules, such as model drug molecules, anti-cancer drugs, oligonucleic acids and so on, under external stimuli, showing great potential in the fields of drug release, gene transfection, sensing etc. Herein, recent research progress on the chemical construction and function study of supramolecular nanovalves based on macrocyclic synthetic receptors was extensively reviewed, together with our own research accomplishment in the field.

Key words: Nanovalve, Supramolecular chemistry, Macrocyclic synthetic receptor, Host-guest chemistry

中图分类号:

O62
O641

TrendMD:

孙宇龙, 杨英威, 邬巍, 张晓安. 基于大环合成受体的超分子纳米阀门. 高等学校化学学报, 2012, 33(08): 1635.

SUN Yu-Long, YANG Ying-Wei, WU Wei, ZHANG Sean Xiao-An. Supramolecular Nanovalve Systems Based on Macrocyclic Synthetic Receptors. Chem. J. Chinese Universities, 2012, 33(08): 1635.

参考文献

[1] Gale P. A.. Chem. Soc. Rev.[J], 2007, 36(2): 141-142 [2] Caltagirone C., Gale P. A.. Chem. Soc. Rev.[J], 2009, 38(2): 520-563 [3] Gokel G. W., Leevy W. M., Weber M. E.. Chem. Rev.[J], 2004, 104(5): 2723-2750 [4] Leininger S., Olenyuk B., Stang P.. J. Chem. Rev.[J], 2000, 100(3): 853-907 [5] Cram D. J., Steinberg H.. J. Am. Chem. Soc.[J], 1951, 73(12): 5691-5704 [6] Hernandez R., Tseng H. R., Wong J. W., Stoddart J. F., Zink J. I.. J. Am. Chem. Soc.[J], 2004, 126(11): 3370-3371 [7] Liu Y., Chen Y.. Acc. Chem. Res.[J], 2006, 39(10): 681-691 [8] Yang Y. W., Chen Y., Liu Y.. Inorg. Chem.[J], 2006, 45(7): 3014-3022 [9] Chen Y., Liu Y.. Chem. Soc. Rev.[J], 2010, 39(2): 495-505 [10] Liu Y., Fan Z., Zhang H. Y., Yang Y. W., Ding F., Liu S. X., Wu X., Wada T., Inoue Y.. J. Org. Chem.[J], 2003, 68(22): 8345-8352 [11] Li L., Zhao M., Li W., Wang Y., Zhang Z., An R., Peng S.. Med. Chem. Commun.[J] 2012, doi: 10.1039/c2md20003a [12] Liu Y., Li L., Zhang H. Y., Song Y.. J. Org. Chem.[J], 2003, 68(2): 527-536 [13] Liu Y., Wang H., Chen Y., Ke C. F., Liu M.. J. Am. Chem. Soc.[J], 2005, 127(2): 657-666 [14] Liu Y., Wang K. R., Guo D. S., Jiang B. P.. Adv. Funct. Mater.[J], 2009, 19(14): 2230-2235 [15] Liu Y., Fan Z., Zhang H. Y., Diao C. H.. Org. Lett.[J], 2003, 5(3): 251-254 [16] Wenz G., Han B. H., Muller A.. Chem. Rev.[J], 2006, 106(3): 782-817 [17] Lee J. W., Samal S., Selvapalam N., Kim H. J., Kim K.. Acc. Chem. Res.[J], 2003, 36(8): 621-630 [18] Kim J., Jung I. S., Kim S. Y., Lee E., Kang J. K., Sakamoto S., Yamaguchi K., Kim K.. J. Am. Chem. Soc.[J], 2000, 122(3): 540-541 [19] Lagona J., Mukhopadhyay P., Chakrabarti S., Isaacs L.. Angew. Chem. Int. Ed.[J], 2005, 44(31): 4844-4870 [20] Mohanty J., Nau W. M.. Angew. Chem. Int. Ed.[J], 2005, 44(24): 3750-3754 [21] Liu Y., Shi J., Chen Y., Ke C. F.. Angew. Chem. Int. Ed.[J], 2008, 47(38): 7293-7296 [22] Han B. H., Liu Y.. Chin. J. Org. Chem.[J], 2003, 23(2): 139-149 [23] Lucas D., Minami T., Iannuzzi G., Cao L., Wittenberg J. B., Anzenbacher P., Isaacs L.. J. Am. Chem. Soc.[J], 2011, 133(44): 17966-17976 [24] Guo D. S., Wang L. H., Liu Y.. J. Org. Chem.[J], 2007, 72(20): 7775-7778 [25] Liu Y., Han B. H., Chen Y. T.. J. Org. Chem.[J], 2000, 65(19): 6227-6230 [26] Guo D. S., Chen K., Zhang H. Q., Liu Y.. Chem. Asian J.[J], 2009, 4(3): 436-445 [27] WANG Kai(王凯), YANG Ying-Wei(杨英威), ZHANG Sean Xiao-An(张晓安). Chem. J. Chinese Universities(高等学校化学学报)[J], 2012, 33(1): 1-13 [28] Shu X., Chen S., Li J., Chen Z., Weng L., Jia X., Li C.. Chem. Commun.[J], 2012, 48: 2967-2969 [29] Liu Y., Yang Y. W., Li L., Chen Y.. Org. Biomol. Chem.[J], 2004, 2(10): 1542-1548 [30] Sun Y. L., Yang B. J., Zhang S. X. A., Yang Y. W.. Chem. Eur. J.[J], 2012, 18(30): 9212-9216 [31] Liu Y., Yang Y. W., Cao R., Song S. H., Zhang H. Y., Wang L. H.. J. Phys. Chem. B[J], 2003, 107(50): 14130-14139 [32] Yang Y. W.. Med. Chem. Commun.[J], 2011, 2(11): 1033-1049 [33] Nguyen T. D., Celestre P. C., Flood A. H., Liu Y., Stoddart J. F., Zink J. I.. Proc. Natl. Acad. Soc.[J], 2005, 102(29): 10029-10034 [34] Rosenholm J. M., Sahlgren C., Lindén M.. Nanoscale[J], 2010, 2(10): 1870-1883 [35] Vallet-Regi M., Rámila A., Real R. P. D., Pérez-Pariente J.. Chem. Mater.[J], 2001, 13(2): 308-311 [36] Leung K. C. F., Nguyen T. D., Stoddart J. F., Zink J. I.. Chem. Mater.[J], 2006, 18(25): 5919-5928 [37] Barbé C., Bartlett J., Kong L., Finnie K., Lin H. Q., Larkin M., Calleja S., Bush A., Calleja G.. Adv. Mater.[J], 2004, 16(21): 1959-1966 [38] Avnir D., Coradin T., Lev O., Livage J.. J. Mater. Chem.[J], 2006, 16(11): 1013-1030 [39] He Q., Shi J.. J. Mater. Chem.[J], 2011, 21(16): 5845-5855 [40] Tao Z., Toms B., Goodisman J., Asefa T.. ACS Nano[J], 2010, 4(2): 789-794 [41] Lei C., Liu P., Chen B., Mao Y., Engelmann H., Shin Y., Jaffar J., Hellstrom I., Liu J., Hellstrom K. E.. J. Am. Chem. Soc.[J], 2010, 132(20): 6906-6907 [42] He Q., Zhang Z., Gao Y., Shi J., Li Y.. Small[J], 2009, 5(23): 2722-2729 [43] Vallet-Regí M., Balas F., Arcos D.. Angew. Chem. Int. Ed.[J], 2007, 46(40): 7548-7558 [44] Meng H., Xue M., Xia T., Zhao Y. L., Tamanoi F., Stoddart J. F., Zink J. I., Nel A. E.. J. Am. Chem. Soc.[J], 2010, 132(36): 12690-12697 [45] Saha S., Leung K. C. F., Nguyen T. D., Stoddart J. F., Zink J. I.. Adv. Funct. Mater.[J], 2007, 17(5): 685-693 [46] Kinbara K., Aida T.. Chem. Rev.[J], 2005, 105(4): 1377-1400 [47] Nguyen T. D., Leung K. C. F., Liong M., Liu Y., Stoddart J. F., Zink J. I.. Adv. Funct. Mater.[J], 2007, 17(13): 2101-2110 [48] Nguyen T. D., Liu Y., Saha S., Leung K. C. F., Stoddart J. F., Zink J. I.. J. Am. Chem. Soc.[J], 2007, 129(3): 626-634 [49] Yang Y. W., Zhang H. Y., Liu Y.. Supramol. Chem.[J], 2008, 20(8): 731-736 [50] Yang Y. W., Li C. J., Zhang H. Y., Liu Y.. Chin. J. Chem.[J], 2004, 22(6): 616-618 [51] Nguyen T. D., Leung K. C. F., Liong M., Pentecost C. D., Stoddart J. F., Zink J. I.. Org. Lett.[J], 2006, 8(15): 3363-3366 [52] Liu Y., Yang Y. W., Chen Y.. Chem. Commun.[J], 2005: 4208-4210 [53] Liu Y., Song S. H., Chen Y., Zhao Y. L., Yang Y. W.. Chem. Commun.[J], 2005: 1702-1704 [54] Liu Y., Yang Y. W., Chen Y., Ding F.. Bioorg. Med. Chem.[J], 2005, 13(4): 963-971 [55] Liu Y., Yang Y. W., Song Y., Zhang H. Y., Ding F., Wada T., Inoue Y.. ChemBioChem[J], 2004, 5(6): 868-871 [56] Liu Y., Yang Y. W., Zhao Y., Li L., Zhang H. Y., Kang S. Z.. J. Incl. Phenom. Macrocycl. Chem.[J], 2003, 47(3/4): 155-160 [57] Liu Y., Yang Y. W., Chen Y., Zou H. X.. Macromolecules[J], 2005, 38(13): 5838-5840 [58] Liu Y., Yang Y. W., Yang E. C., Guan X. D.. J. Org. Chem.[J], 2004, 69(20): 6590-6602 [59] Liu Y., Yang E. C., Yang Y. W., Zhang H. Y., Fan Z., Ding F., Cao R.. J. Org. Chem.[J], 2004, 69(1): 173-180 [60] Liu Y., Yang Y. W., Zhang H. Y., Hu B. W., Ding F., Li C. J.. Chem. Biodiv.[J], 2004, 1(3): 481-488 [61] Park C., Oh K., Lee S. C., Kim C.. Angew. Chem. Int. Ed.[J], 2007, 46(9): 1455-1457 [62] Du L., Liao S., Khatib H. A., Stoddart J. F., Zink J. I.. J. Am. Chem. Soc.[J], 2009, 131(42): 15136-15142 [63] Du L., Song H., Liao S.. Microporous Mesoporous Mater.[J], 2012, 147(1): 200-204 [64] Zhao Y. L., Li Z., Kabehie S., Botros Y. Y., Stoddart J. F., Zink J. I.. J. Am. Chem. Soc.[J], 2010, 132(37): 13016-13025 [65] Kim H., Kim S., Park C., Lee H., Park H. J., Kim C.. Adv. Mater.[J], 2010, 22(38): 4280-4283 [66] Ambrogio M. W., Pecorelli T. A., Patel K., Khashab N. M., Trabolsi A., Khatib H. A., Botros Y. Y., Zink J. I., Stoddart J. F.. Org. Lett.[J], 2010, 12(15): 3304-3307 [67] Wang C., Li Z., Cao D., Zhao Y. L., Gaines J. W., Bozdemir O. A., Ambrogio M. W., Frasconi M., Botros Y. Y., Zink J. I., Stoddart J. F.. Angew. Chem. Int. Ed.[J], 2012, 51(22): 5460-5465 [68] Khashab N. M., Trabolsi A., Lau Y. A., Ambrogio M. W., Friedman D. C., Khatib H. A., Zink J. I., Stoddart J. F.. Eur. J. Org. Chem.[J], 2009, 2009(11): 1669-1673 [69] Ferris D. P., Zhao Y. L., Khashab N. M., Khatib H. A., Stoddart J. F., Zink J. I.. J. Am. Chem. Soc.[J], 2009, 131(5): 1686-1688 [70] Patel K., Angelos S., Dichtel W. R., Coskun A., Yang Y. W., Zink J. I., Stoddart J. F.. J. Am. Chem. Soc.[J], 2008, 130(8): 2382-2383 [71] Park C., Kim H., Kim S., Kim C.. J. Am. Chem. Soc.[J], 2009, 131(46): 16614-16615 [72] Behrend R., Meyer E., Rusche F.. Liebigs Ann. Chem.[J], 1905, 339: 1-37 [73] Freeman W. A., Mock W. L., Shih N. Y.. J. Am. Chem. Soc.[J], 1981, 103(24): 7367-7368 [74] Day A., Arnold A. P., Blanch R. J., Snushall B.. J. Org. Chem.[J], 2001, 66(24): 8094-8100 [75] Bardelang D., Udachin K. A., Leek D. M., Margeson J. C., Chan G., Ratcliffe C. I., Ripmeester J. A.. Cryst. Growth Des.[J], 2011, 11(12): 5598-5614 [76] Jon S. Y., Selvapalam N., Oh D. H., Kang J. K., Kim S. Y., Jeon Y. J., Lee J. W., Kim K.. J. Am. Chem. Soc.[J], 2003, 125(34): 10186-10187 [77] Wu A., Chakraborty A., Witt D., Lagona J., Damkaci F., Ofori M. A., Chiles J. K., Fettinger J. C., Isaacs L.. J. Org. Chem.[J], 2002, 67(16): 5817-5830 [78] Angelos S., Yang Y. W., Patel K., Stoddart J. F., Zink J. I.. Angew. Chem. Int. Ed.[J], 2008, 47(12): 2222-2226 [79] Angelos S., Khashab N. M., Yang Y. W., Trabolsi A., Khatib H. A., Stoddart J. F., Zink J. I.. J. Am. Chem. Soc.[J], 2009, 131(36): 12912-12914 [80] Khashab N. M., Belowich M. E., Trabolsi A., Friedman D. C., Valente C., Lau Y., Khatib H. A., Zink J. I., Stoddart J. F.. Chem. Commun.[J], 2009, 36: 5371-5373 [81] Thomas C. R., Ferris D. P., Lee J. H., Choi E., Cho M. H., Kim E. S., Stoddart J. F., Shin J. S., Cheon J., Zink J. I.. J. Am. Chem. Soc.[J], 2010, 132(31): 10623-10625 [82] Angelos S., Yang Y. W., Khashab N. M., Stoddart J. F., Zink J. I.. J. Am. Chem. Soc.[J], 2009, 131(32): 11344-11346