Chinese Journal of Organic Chemistry >
Research Advances of KRN7000 Analogues and Their Immune Activities
Received date: 2014-09-30
Revised date: 2014-12-06
Online 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 (TH2) and IL-4 inhibited the activity of T helper 1 cells (TH1), which mediated humoral as well as celluar immune reactions, respectively. The concomitant of functions of TH1 and TH2 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; TH1/TH2
Feng Junna , Gao Fang , Peng Shaohui , Chen Hu , Li Xiaoliu . Research Advances of KRN7000 Analogues and Their Immune Activities[J]. Chinese Journal of Organic Chemistry, 2015 , 35(5) : 997 -1008 . DOI: 10.6023/cjoc201409048
[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.
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