Research Advances of KRN7000 Analogues and Their Immune Activities

doi:10.6023/cjoc201409048

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (5): 997-1008.DOI: 10.6023/cjoc201409048 Previous Articles Next Articles

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KRN7000结构类似物及其免疫活性研究进展

冯俊娜^a,b, 高芳^a, 彭绍辉^b, 陈华^a, 李小六^a

a 河北大学化学与环境科学学院保定 071002;
b 中国地质大学长城学院保定 071000

收稿日期:2014-09-30 修回日期:2014-12-06 发布日期:2014-12-18
通讯作者: 陈华, 李小六 E-mail:hua-todd@163.com;lixl@hbu.cn
基金资助:
国家自然科学基金(Nos.20972039,21372060)、教育部博士点基金(No.20121301110004)、河北省自然科学基金石药集团医药联合基金(No.B2011201169)、河北省教育厅自然科学基金(No.ZH2011110)资助项目.

Research Advances of KRN7000 Analogues and Their Immune Activities

Feng Junna^a,b, Gao Fang^a, Peng Shaohui^b, Chen Hu^a, Li Xiaoliu^a

a College of Chemistry and Environmental Science, Hebei University, Baoding 071002;
b China University of Geosciences Great Wall College, Baoding 071000

Received:2014-09-30 Revised:2014-12-06 Published:2014-12-18
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.20972039, 21372060), the Research Fund for the Doctoral Program of Higher Education of China (No.20121301110004), the Medicinal Joint Funds of the Natural Science Foundation of Hebei and Shijiazhuang Pharmaceutical Group Foundation (No.B2011201169), and the Natural Science Foundations of Education Department of Hebei Province (No.ZH2011110).

KRN7000 has widely biological activities, such as anti-tumor, anti-tuberculosis, anti-fungal, anti-virus, anti-inflammation, and against auto-immune diseases. As the potential immunomodulator, KRN7000 can effectively activate the natural killer T cells (NKT cells) and induce the secretion of IFN-γ and IL-4 cytokines. However, IFN-γ inhibited the activity of T helper 2 cells (T_H2) and IL-4 inhibited the activity of T helper 1 cells (T_H1), which mediated humoral as well as celluar immune reactions, respectively. The concomitant of functions of T_H1 and T_H2 limits the therapeutic potential of KRN7000 against immune diseases. Therefore, developing new analogues of KRN7000 to find new immnostimulating drugs has drawn many attentions in the world. This review presents the recent progress in the study on the structure and immune activity of the synthesized KRN7000 derivatives.

Key words: KRN7000, immunomodulator, T_H1/T_H2

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Feng Junna, Gao Fang, Peng Shaohui, Chen Hu, Li Xiaoliu. Research Advances of KRN7000 Analogues and Their Immune Activities[J]. Chin. J. Org. Chem., 2015, 35(5): 997-1008.

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[1] Natori, T.; Morita, M.; Akimoto, K.; Koezuka, Y. Tetrahedron 1994, 50, 2771.
[2] Uchida, T.; Horiguchi, S.; Tanaka, Y.; Yamamoto, H.; Kunii, N.; Motohashi, S.; Taniguchi, M.; Nakayama, T.; Okamoto, Y. Cancer Immunol. Immun. 2008, 57, 337.
[3] Chackerian, A.; Alt, J.; Perera, V.; Behar, S, M. Infect. Immun. 2002, 70, 6302.
[4] Hung, J.-T. Tsai, Y.-C.; Lin, W.-D.; Jan, J.-T.; Lin, K.-H.; Huang, J.-R.; Cheng, J.-Y.; Chen, M.-W.; Wong, C.-H.; Yu, A. L. Antiviral Res. 2014, 107, 110.
[5] Kawakami, K.; Kinjo, Y,; Yara, S.; Koguchi, Y.; Uezu, K.; Nakayama, T.; Tanigushi, M.; Saito, A. Infect. Immun. 2001, 69, 213.
[6] Dieli, F.; Taniguchi, M.; Kronenberg, M.; Sidobre, S.; Ivanyi, J.; Fattorini, L.; Iona, E.; Orefici, G.; Leo, G. D.; Russo, D; Caccamo, N.; Sireci, G.; Sano, C. D.; Salerno, A. J. Immunol. 2003, 171, 1961.
[7] Singh, A. K.; Yang, J.-Q.; Parekh, V. V.; Wei, J.; Wang, C.-R.; Joyce, S.; Singh, R. R.; Kaer, L. V. Eur. J. Immunol. 2005, 35, 1143.
[8] Duarte, N.; Stenstrom, M.; Campino, S.; Bergman, M.-L.; Lundholm, M.; Holmberg, D.; Cardell, S. L. J. Immunol. 2004, 173, 3112.
[9] Kobayashi, E.; Motoki, K.; Yamaguchi, Y.; Uchida, T.; Fukushima, H.; Koezuka, Y. Bioorg. Med. Chem. Lett. 1996, 4, 615.
[10] Motohashi, S.; Nagato, K.; Kunii, N.; Yamamoto, H.; Yamasaki, K.; Okita, K.; Hanaoka, H.; Shimizu, N.; Suzuki, M.; Yoshino, I.; Taniguchi, M.; Fujisawa, T.; Nakayama, T. J. Immunol. 2009, 182, 2492.
[11] Singh, N.; Hong, S.; Scherer, D. C.; Serizawa, I.; Burdin, N.; Kronenberg, M.; Koezuka, Y.; Kaer, L. V. J. Immunol. 1999, 163, 2373.
[12] Yen, Y.-F.; Kulkarni, S. S; Chang, C.-W.; Luo, S. Y. Carbohydr. Res. 2013, 368, 35.
[13] Franck, R. W.; Tsuji, M. Acc. Chem. Res. 2006, 39, 692.
[14] Zhang, L.; Ye. X. S. J. Chin. Pharm. Sci. 2008, 17, 263.
[15] Banchet-Cadeddu, A.; Hénon, E.; Dauchez, M.; Renault, J.-H.; Monneaux, F.; Haudrechy, A. Org. Biomol. Chem. 2011, 9, 3080.
[16] Nadas, J.; Li, C.; Wang, P. G. J. Chem. Inf. Model. 2009, 49, 410.
[17] Kawano, T.; Cui, J.; Koezuka, Y.; Toura, I.; Kaneko, Y.; Motoki, K.; Ueno, H.; Nakagawa, R.; Sato, H.; Kondo, E.; Koseki, H.; Taniguchi, M. Science 1997, 278, 1626.
[18] Raju, R.; Castillo, B. F.; Richardson, S. K.; Thakur, M.; Severins, R.; Kronenberg, M.; Howell, A. R. Bioorg. Med. Chem. Lett. 2009, 19, 4122.
[19] Xing, G.-W.; Wu, D.; Poles, M. A.; Horowitz, A.; Tsuji, M.; Ho, D. D.; Wong, C.-H. Bioorg. Med. Chem. Lett. 2005, 13, 2907.
[20] Zhou, D.; Mattner, J.; Cantu III, C.; Schrantz, N.; Yin, N.; Gao, Y.; Sagiv, Y.; Hudspeth, K.; Wu, Y.-P.; Yamashita, T.; Tenenberg, S.; Wang, D.; Proia, R. L.; Levery, S. B.; Savage, P. B.; Teyton, L.; Bendelac, A. Science 2004, 306, 1786.
[21] Veerapen, N.; Brigl, M.; S. Cerundolo, G, V.; Cox, L. R.; Brenner, M. B.; Besra, G. S. Bioorg. Med. Chem. Lett. 2009, 19, 4288.
[22] Jervis, P. J.; Graham, L. M.; Foster, E. L.; Cox, L. R.; Porcelli, S. A.; Besra, G. S. Bioorg. Med. Chem. Lett. 2012, 22, 4348.
[23] Tashiro, T.; Nakagawa, R.; Inoue, S.; Shiozaki, M.; Watarai, H.; Taniguchi, M.; Mori, K. Tetrahedron Lett. 2008, 49, 6827.
[24] Tashiro, T.; Nakagawa, R.; Shigeura, T.; Watarai, H.; Taniguchi, M.; Mori, K. Bioorg. Med. Chem. 2013, 21, 3066.
[25] Pauwels, N.; Aspeslagh, S.; Vanhoenacker, G.; Sandra, K.; Yu, E. D.; Zajonc, D. M.; Elewaut, D.; Linclau, B.; Van Calenbergh, S. Org. Biomol. Chem. 2011, 9, 8413.
[26] Chang, Y.-J.; Huang, J.-R.; Tsai, Y.-C.; Hung, J.-T.; Wu, D.; Fujio, M.; Wong, C.-H.; Yu, A. L. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 10299.
[27] Ebensen, T.; Link, C.; Riese, P.; Schulze, K.; Morr, M.; Guzman, C. A. J. Immunol. 2007, 179, 2065.
[28] Tashiro, T.; Nakagawa, R.; Hirokawa, T.; Inoue, S.; Watarai, H.; Taniguchi, M.; Mori, K. Bioorg. Med. Chem. Lett. 2009, 17, 6360.
[29] Silk, J. D.; Salio, M.; Reddy, B. G.; Shepherd, D.; Gileadi, U.; Brown, J.; Masri, S. H.; Polzella, P.; Ritter, G.; Besra, G. S.; Jones, E. Y.; Schmidt, R. R.; Cerundolo, V. J. Immunol. 2008, 180, 6452.
[30] Diaz, G. Y. R.; Wojno, J.; Cox, L. R.; Besra, G. S. Tetrahedron: Asymmetry 2009, 20, 747.
[31] Tomiyama, H.; Yanagisawa, T.; Nimura, M.; Noda, A.; Tomiyama, T. JP 2001/354666, 2002 [Chem. Abstr. 2002, 136, 37901x; US 2002/0032158, 2002].
[32] Li, X.; Shiratsuchi, T.; Chen, G.; Dellabona, P.; Casorati, G.; Franck, R. W.; Tsuji, M. J. Immunol. 2009, 183, 4415.
[33] Altiti, A. S.; Mootoo, D. R. Org. Lett. 2014, 16, 1466.
[34] Liu, Z.; Byun, H. S.; Bittman, R. J. Org. Chem. 2011, 76, 8588.
[35] Liu, Z.; Byun, H. S.; Bittman, R. Org. Lett, 2010, 12, 2974.
[36] Toba, T.; Murata, K.; Yamamura, T.; Miyakeb, S.; Annoura, H. Tetrahedron Lett. 2005, 46, 5043.
[37] Pu, J.; Franck, R. W. Tetrahedron 2008, 64, 8618.
[38] Liu, Z.; Bittman, R. Org. Lett. 2012, 14, 620.
[39] Li, X.; Chen, G.; Garcia-Navarro, R.; Franck, R. W.; Tsuji, M. Immunology 2008, 127, 216.
[40] Lu, X; Song, L.; Metelitsa, L. S.; Bittman, R. ChemBioChem. 2006, 7, 1750.
[41] Blauvelt, M. L.; Khalili, M.; Jaung, W.; Paulsen, J.; Anderson, A. C.; Wilson, S. B.; Howell, A. R. Bioorg. Med. Chem. Lett. 2008, 18, 6374.
[42] Sun, M.; Wang, Y.; Ye, X.-S. Tetrahedron 2013, 69, 7438.
[43] Chen, W.; Xia, C.; Cai, L.; Wang, P. G. Bioorg. Med. Chem. Lett. 2010, 20, 3859.
[44] McDonagh, A. W.; Murphy, P. V. Tetrahedron 2014, 70, 3191.
[45] Park, J.-J.; Lee, J. H.; Ghosh, S. C.; Bricard, G.; Venkataswamy, M. M.; Porcelli, S. A.; Chung, S.-K. Bioorg. Med. Chem. Lett. 2008, 18, 3906.
[46] Lacone, V.; Hunault, J.; Pipelier, M.; Blot, V.; Lecoert, T.; Rocher, J.; Turcot-Dubois, A.-L.; Marionneau, S.; Douillard, J.-Y.; Clement, M.; Pendu, J. L.; Bonneville, M.; Micouin, L.; Dubreuil, D. J. Med. Chem. 2009, 52, 4960.
[47] Baek, D. J.; Seo, J.-H.; Lim, C.; Kim, J. H.; Chung, D. H.; Cho, W.-J.; Kang, C.-Y.; Kim, S. ACS Med. Chem. Lett. 2011, 2, 544.
[48] Hunault, J.; Diswall, M.; Frison, J.-C.; Blot, V.; Rocher, J.; Marionneau-Lambot, S.; Oullier, T.; Douillard, J.-Y.; Guillarme, S.; Saluzzo, C.; Dujardin, G.; Jacquemin, D.; Graton, J.; Questel, J.-Y. L.; Evain, M.; Lebreton, J.; Dubreuil, D.; Pendu, J. L.; Pipelier, M. J. Med. Chem. 2012, 55, 1227.
[49] Leung, L.; Tomassi, C.; Van Beneden, K.; Decruy, T.; Elewaut, D.; Elliott, T.; Al-Shamkhani, A.; Ottensmeier, C.; Calenbergh, S. V.; Werner, J.; Williams, T.; Linclau, B. Org. Lett. 2008, 10, 4433.
[50] Trappeniers, M.; Chofor, R.; Aspeslagh, S.; Li, Y.; Linclau, B.; Zajonc, D. M.; Elewaut, D.; Calenbergh, S. V. Org. Lett. 2010, 12, 2928.
[51] Fan, G.-T.; Pan, Y.-S.; Lu, K.-C.; Cheng, Y.-P.; Lin, W.-C.; Lin, S.; Lin, C.-H.; Wong, C.-H.; Fanga J.-M.; Lin, C.-C. Tetrahedron 2005, 61, 1855.
[52] Hung, L.-C.; Lin, C.-C.; Hung, S.-K.; Wu, B.-C.; Jan, M.-D.; Liou, S.-H. Fu, S.-L. Biochem. Pharmacol. 2007, 73, 1957.
[53] Shiozaki, M.; Tashiro, T.; Koshino, H.; Shigeura, T.; Watarai, H.; Taniguchi, M.; Mori, K. Carbohydr. Res. 2013, 370, 46.
[54] Shiozaki, M.; Tashiro, T.; Koshino, H.; Shigeura, T.; Watarai, H.; Taniguchi, M.; Mori, K. Bioorg. Med. Chem. 2014, 22, 827.
[55] Sawant, R. C.; Hung, J.-T.; Chuang, H.-L.; Lin, H.-S.; Chen, W.-S.; Yu, A. L.; Luo, S.-Y. Eur. J. Org. Chem. 2013, 7611.
[56] Lee, T.; Cho, M.; Ko, S.-Y.; Youn, H.-J.; Baek, D. J.; Cho, W.-J.; Kang, C.-Y.; Kim, S. J. Med. Chem. 2007, 50, 585.
[57] Tashiro, T.; Shigeura, T.; Watarai, H.; Taniguchi M.; Mori, K. Bioorg. Med. Chem. 2012, 20, 4540.
[58] Shiozaki, M.; Tashiro, T.; Koshino, H.; Nakagawa, R.; Inoue, S.; Shigeura, T.; Watarai, H.; Taniguchi, M.; Mori, K. Carbohydr. Res. 2010, 345, 1663.
[59] Shiozaki, M.; Tashiro, T.; Koshino, H.; Shigeura, T.; Watarai, H.; Taniguchi, M.; Mori, K. Tetrahedron 2013, 69, 9710
[60] Tashiro, T.; Shigeura, T.; Shiozaki, M.; Watarai, H.; Taniguchi, M.; Mori, K. Med. Chem. Commun. 2013, 4, 949.
[61] Fuhshuku, K.-I.; Hongo, N.; Tashiro, T.; Masuda, Y.; Nakagawa, R.; Seino, K.-I.; Taniguchi, M.; Mori, K. Bioorg. Med. Chem. 2008, 16, 950.
[62] Velmourougane, G.; Raju, R.; Bricard, G.; Im, J. S.; Besra, G. S.; Porcelli, S. A.; Howell, A. R. Bioorg. Med. Chem. Lett. 2009, 19, 3386.
[63] Toba, T.; Murata, K.; Nakanishi, K.; Takahashi, B.; Takemoto, N.; Akabane, M.; Nakatsuka, T.; Imajo, S.; Yamamura, T.; Miyake, S.; Annoura, H. Bioorg. Med. Chem. Lett. 2007, 17, 2781.
[64] Veerapen, N.; Reddington, F.; Salio, M.; Cerundolo, V.; Besra, G. S. Bioorg. Med. Chem. 2011, 19, 221.
[65] Yu, K. O. A.; Im, J. S.; Molano, A.; Dutronc, Y.; Illarionov, P. A.; Forestier, C.; Fujiwara, N.; Arias, I.; Miyake, S.; Yamamura, T.; Chang, Y.-T.; Besra, G. S.; Porcelli, S. A. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 3383.
[66] Fujio, M.; Wu, D.; Garcia-Navarro, R.; Ho, D. D.; Tsuji, M.; Wong, C.-H. J. Am. Chem. Soc. 2006, 128, 9022.
[67] Matto, P.; Modica, E.; Franchini, L.; Facciotti, F.; Mori, L.; Libero, G. D.; Lombardi, G.; Fallarini, S.; Panza, L.; Compostella, F.; Ronchetti, F. J. Org. Chem. 2007, 72, 7757.
[68] Park, J.-J.; Lee, J. H.; Seo, K.-C.; Bricard, G.; Venkataswamy, M. M.; Porcelli, S. A.; Chung, S.-K. Bioorg. Med. Chem. Lett. 2010, 20, 814. 、
[69] Michieletti, M.; Bracci, A.; Compostella, F.; De Libero, G.; Mori, L.; Fallarini, S.; Lombardi, G.; Panza, L. J. Org. Chem. 2008, 73, 9192.
[70] Kim, Y.; Kim, J.; Oh, K.; Lee, D.-S.; Park, S. B. ACS Med. Chem. Lett. 2012, 3, 151.
[71] Zhou, X.-T.; Forestier, C.; Goff, R. D.; Li, C.; Teyton, L.; Bendelac, A.; Savage, P. B. Org. Lett. 2002, 4, 1367.
[72] Sakai, T.; Naidenko, O. V.; Iijima, H.; Kronenberg, M.; Koezuka, Y. J. Med. Chem. 1999, 42, 1836.
[73] Sakai, T.; Ehara, H.; Koezuka, Y. Org. Lett. 1999, 1, 359.
[74] Vo-Hoang, Y.; Micouin, L.; Ronet, C.; Gachelin, G.; Bonin, M. ChemBioChem 2003, 4, 27.
[75] Stocker, B. L.; Timmer, M. S. M. Carbohydr. Res. 2014, 389, 3.

KRN7000结构类似物及其免疫活性研究进展

Research Advances of KRN7000 Analogues and Their Immune Activities

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