Chinese Journal of Organic Chemistry >
Research Progress in Prodrugs of Acyclic Nucleoside Phosphonates Antiviral Agents
Received date: 2018-08-16
Revised date: 2018-10-15
Online published: 2018-11-30
Supported by
Project supported by the Natural Science Foundation of Hebei Province (No.H2018307055) and the Technology Innovation Foundation of Hebei Normal University (No.L2017K06).
More and more attention has been focused on acyclic nucleoside phosphonates (ANPs) antiviral agents which were wildly used in clinical therapy. However, poor oral bioavailability and high toxicity directly related to the phosphonate charge were serious and unnegligible especially for the treatment of chronic diseases such as hepatitis B virus (HBV) and human immunodeficiency virus (HIV). Preparing appropriate forms of prodrug could enhance the oral bioavailability and reduce the toxicity because of the smooth absorption of prodrugs and the release of active drug only at the target. This review summarizes some recent progress in prodrugs of ANPs antiviral agents based on the structures of tenofovir, adefovir and cidofovir.
Gao Mengyuana , Liu Hongtaob , Lian Yufeib , Gao Xinfenga , Geng Yunhea , Li Wenyan . Research Progress in Prodrugs of Acyclic Nucleoside Phosphonates Antiviral Agents[J]. Chinese Journal of Organic Chemistry, 2019 , 39(4) : 974 -981 . DOI: 10.6023/cjoc201808018
[1] (a) De Clercq, E. Biochem. Pharmacol. 2013, 86, 711.
(b) De Clercq, E. Adv. Pharmacol. 2013, 67, 293.
(c) De Clercq, E.; Holy, A. Nat. Rev. Drug Discovery 2005, 4, 928.
(d) Liu, K.; Xie, L. Acta Pharm. Sin. 2006, 41, 689(in Chinese).(刘琨, 谢蓝, 药学学报, 2006, 41, 689.)
[2] (a) De Clercq, E. Expert. Rev. Anti-Infect. Ther. 2003, 1, 21.
(b) De Clercq, E. Biochem. Pharmacol. 2011, 82, 99.
(c) De Clercq, E. Med. Res. Rev. 2013, 33, 1278.
[3] Peng, Y. M.; Yu, W. Q.; Li, E. T.; Kang, J. F.; Wang, Y. F.; Yang, Q. H.; Liu, B. J.; Zhang, J. M.; Li, L. Y.; Wu, J.; Jiang, J. H.; Wang, Q. D.; Chang, J. B. J. Med. Chem. 2016, 59, 3661.
[4] Pertusati, F.; Serpi, M.; McGuigan, C. Antivir. Chem. Chemother. 2012, 22, 181.
[5] De Clercq, E. Clin. Microbiol. Rev. 2003, 16, 569.
[6] De Clercq, E. Antiviral Res. 2007, 75, 1.
[7] (a) Krecmerova, M. Mini-Rev. Med. Chem. 2017, 17, 818.
(b) Hecker, S. J.; Erion, M. D. J. Med. Chem. 2008, 51, 2328.
(c) Wiemer, A. J.; Wiemer, D. F. Top. Curr. Chem. 2015, 360, 115.
(d) Xie, M. S.; Chen, Y. G.; Wu, X. X.; Qu, G. R.; Guo, H. M. Org. Lett. 2018, 20, 1212.
[8] (a) Yang, K. H.; Wang, J. T.; Li, Q. B.; Xu, W. F. Food Drug 2018, 10, 60(in Chinese).(杨康辉, 王举涛, 李乾斌, 徐文方, 食品与药品, 2018, 10, 60.)
(b) Wang, S. X.; Duan, H. D.; Meng, X.; Qin, D. W.; Wang, L. Z.; Li, X. M. J. Beijing Union Univ. (Nat. Sci.) 2010, 24, 29(in Chinese).(王世潇, 段洪东, 孟霞, 秦大伟, 王利振, 李晓萌, 北京联合大学学报(自然科学版), 2010, 24, 29.)
(c) Li, W. B.; Dong, F. H.; Sun, C. J. Prog. Pharm. Sci. 2012, 36, 300(in Chinese).(李文保, 董芳华, 孙昌俊, 药学进展, 2012, 36, 300.)
[9] Kearney, B. P.; Flaherty, J. F.; Shah, J. Clin. Pharmacokinet. 2004, 43, 595.
[10] Nelson, M. R.; Katlama, C.; Montaner, J. S.; Cooper, D. A.; Gazzard, B.; Clotet, B.; Lazzari, A.; Schewe, K.; Lange, J.; Wyatt, C. AIDS 2007, 21, 1273.
[11] Barditch-Crovo, P.; Deeks, S. G.; Collier, A.; Safrin, S.; Coakley, D. F.; Miller, M.; Kearney, B. P.; Coleman, R. L.; Lamy, P. D.; Kahn, J. O. Antimicrob. Agents Chemother. 2001, 45, 2733.
[12] Ray, A. S.; Fordyce, M. W.; Hitchcock, M. J. M. Antiviral Res. 2016, 125, 63.
[13] Ruane, P. J.; DeJesus, E.; Berger, D.; Markowitz, M.; Bredeek, U. F.; Callebaut, C.; Zhong, L.; Ramanathan, S.; Rhee, M. S.; Fordyce, M. W. J. Acquired Immune Defic. Syndr. 2013, 63, 449.
[14] (a) Sax, P. E.; Zolopa, A.; Brar, I.; Elion, R.; Ortiz, R.; Post, F.; Wang, H.; Callebaut, C.; Martin, H.; Fordyce, M. W. J. J. Acquired Immune Defic. Syndr. 2014, 67, 52.
(b) Zhang, X. Q. Acta. Pharm. Sin. 2015, 50, 509(in Chinese).(张兴权, 药学学报, 2015, 50, 509.)
[15] Painter, G. R.; Almond, M. R.; Trost, L. C.; Lampert, B. M.; Neyts, J.; De Clercq, E.; Korba, B. E.; Aldern, K. A.; Beadle, J. R.; Hostetler, K. Y. Antimicrob. Agents Chemother. 2007, 51, 3505.
[16] Lanier, E. R.; Lampert, B.; Trost, L.; Painter, G.; Almond, M. Antiviral Ther. 2008, 13, A6.
[17] Tanwandee, T.; Chatsiricharoenkul, S.; Thongsawat, S.; Sukeepaisarnjaroen, W.; Tangkijvanich, P.; Komolmit, P.; Avihingsanon, A.; Piratvisuth, T.; Sunthi, P.; Mahasanprasert, T. J. Hepatol. 2017, 66, S24.
[18] Chatsiricharoekul, S.; Jutasompakorn, P.; Niyomnaitham, S.; Matkovits, T.; Conover, M.; Cobb, J.; Greytok, J.; Sullivan-Bolyai, J. Clin. Pharmacol. Ther. 2017, 101, S48.
[19] Giesler, K. E.; Marengo, J.; Liotta, D. C. J. Med. Chem. 2016, 59, 7097.
[20] Giesler, K. E.; Liotta, D. C. J. Med. Chem. 2016, 59, 10244.
[21] Marcellin, P.; Chang, T.-T.; Lim, S. G.; Tong, M. J.; Sievert, W.; Shiffman, M. L.; Jeffers, L.; Goodman, Z.; Wulfsohn, M. S.; Xiong, S. N. Engl. J. Med. 2003, 348, 808.
[22] Marcellin, P.; Chang, T.-T.; Lim, S. G. L.; Sievert, W.; Tong, M.; Arterburn, S.; Borroto-Esoda, K.; Frederick, D.; Rousseau, F. Hepatology 2008, 48, 750.
[23] Ingiliz, P.; Valantin, M.-A.; Thibault, V.; Duvivier, C.; Dominguez, S.; Katlama, C.; Poynard, T.; Benhamou, Y. Antivir. Ther. 2008, 13, 895.
[24] Reddy, K. R.; Matelich, M. C.; Ugarkar, B. G.; Gomez-Galeno, J. E.; DaRe, J.; Ollis, K.; Sun, Z.; Craigo, W.; Colby, T. J.; Fujitaki, J. M. J. Med. Chem. 2008, 51, 666.
[25] Lin, C. C.; Fang, C.; Benetton, S.; Xu, G. F.; Yeh, U. T. Antimicrob. Agents Chemother. 2006, 50, 2926.
[26] Ding, Y.; Zhang, H.; Li, X.; Li, C.; Chen, G.; Chen, H.; Wu, M.; Niu, J. Hepatol. Int. 2017, 11, 390.
[27] Fu, X.; Jiang, S.; Li, C.; Xin, J.; Yang, Y.; Ji, R. Bioorg. Med. Chem. Lett. 2007, 17, 465.
[28] Fu, X. Z.; Wang, Y. L.; Lan, Y. Y.; Wang, A. M.; Ou, Y.; Luo, C.; Li, Y. Acta Pharm. Sin. 2010, 45, 1017(in Chinese).(傅晓钟, 王永林, 兰燕宇, 王爱民, 欧瑜, 罗春, 李燕, 药学学报, 2010, 45, 1017.)
[29] Fu, X.-Z.; Ou, Y.; Pei, J.-Y.; Liu, Y.; Li, J.; Zhou, W.; Lan, Y.-Y.; Wang, A.-M.; Wang, Y.-L. Eur. J. Med. Chem. 2012, 49, 211.
[30] Magee, W. C.; Evans, D. H. Antiviral Res. 2012, 96, 169.
[31] (a) De Clercq, E. Trends Pharmacol. Sci. 2002, 23, 456.
(b) Andrei, G.; Topalis, D.; De Schutter, T.; Snoeck, R. Antiviral Res. 2015, 114, 21.
[32] Cundy, K. C.; Bidgood, A. M.; Lynch, G.; Shaw, J. P.; Griffin, L.; Lee, W. A. Drug. Metab. Dispos. 1996, 24, 745.
[33] (a) Beadle, J. R.; Hartline, C.; Aldern, K. A.; Rodriguez, N.; Harden, E.; Kern, E. R.; Hostetler, K. Y. Antimicrob. Agents Chemother. 2002, 46, 2381.
(b) Hostetler, K. Y. Viruses 2010, 2, 2213.
[34] Marty, F. M.; Winston, D. J.; Rowley, S. D.; Vance, E.; Papanicolaou, G. A.; Mullane, K. M.; Brundage, T. M.; Robertson, A. T.; Godkin, S.; Mommeja-Marin, H. N. Engl. J. Med. 2013, 369, 1227.
[35] Marty, F. M.; Winston, D. J.; Chemaly, R. F.; Boeckh, M. J.; Mullane, K. M.; Shore, T. B.; Papanicolaou, G. A.; Morrison, M. E.; Brundage, T. M.; Mommeja-Marin, H. Biol. Blood Marrow. Transplant. 2016, 22, S23.
[36] (a) Florescu, D.; Grimley, M.; Papanicolaou, G.; Prasad, V.; Vainorius, E.; Chittick, G.; Brundage, T.; Nichols, G. Am. J. Transplant. 2018, 18, S360.
(b) Chittick, G.; Morrison, M.; Brundage, T.; Nichols, W. G. Antivir. Res. 2017, 143, 269.
[37] Dunning, J.; Kennedy, S. B.; Antierens, A.; Whitehead, J.; Ciglenecki, I.; Carson, G.; Kanapathipillai, R.; Castle, L.; Howell-Jones, R.; Pardinaz-Solis, R. PLoS One 2016, 11, e0162199.
[38] Lampertico, P. Gut 2014, 63, 869.
[39] Mak, L.-Y.; Seto, W.-K.; Lai, C.-L.; Yuen, M.-F. Expert Opin. Drug Metab. Toxicol. 2018, 14, 101.
[40] Ahn, S. H.; Kim, W.; Jung, Y. K.; Yang, J. M.; Jang, J. Y.; Kweon, Y. O.; Cho, Y. K.; Kim, Y. J.; Hong, G. Y.; Kim, D. J. J. Hepatol. 2017, 66, S88.
[41] Lai, C.-L.; Ahn, S. H.; Lee, K. S.; Um, S. H.; Cho, M.; Yoon, S. K.; Lee, J.-W.; Park, N. H.; Kweon, Y.-O.; Sohn, J. H. Gut 2014, 63, 996.
[42] Yuen, M.-F.; Ahn, S. H.; Lee, K. S.; Um, S. H.; Cho, M.; Yoon, S. K.; Lee, J.-W.; Park, N. H.; Kweon, Y. O.; Sohn, J. H. Hepatology 2013, 58, 693A.
[43] Yuen, M.-F.; Ahn, S. H.; Lee, K. S.; Um, S. H.; Cho, M.; Yoon, S. K.; Lee, J.-W.; Park, N. H.; Kweon, Y.-O.; Sohn, J. H. J. Hepatol. 2015, 62, 526.
[44] Baszczynski, O. Janeba, Z. Med. Res. Rev. 2013, 33, 1304.
[45] Luo, M.; Groaz, E.; Andrei, G.; Snoeck, R.; Kalkeri, R.; Ptak, R. G.; Hartman, T.; Buckheit, R. W., Jr.; Schols, D.; De Jonghe, S. J. Med. Chem. 2017, 60, 6220.
[46] Holy, A.; Gunter, J.; Dvorakova, H.; Masojidkova, M.; Andrei, G.; Snoeck, R.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1999, 42, 2064.
[47] Jansa, P.; Baszczyňski, O.; Dracínský, M.; Votruba, I.; Zídek, Z.; Bahador, G.; Stepan, G.; Cihlar, T.; Mackman, R.; Holý, A; Jansa, Z. Eur. J. Med. Chem. 2011, 46, 3748.
/
| 〈 |
|
〉 |