Recent Topics in Research and Development of Opioid Drugs
- Corresponding author: Shen Yuehai, yuehaishen@kmust.edu.cn
Citation:
Pan Chenling, Meng Hao, Wang Liangliang, Shen Yuehai, Zuo Zhili, Wang Guanlin, Chang Kwen-jen. Recent Topics in Research and Development of Opioid Drugs[J]. Chinese Journal of Organic Chemistry,
;2018, 38(10): 2625-2632.
doi:
10.6023/cjoc201804025
Feng, Y.; He, X. Z.; Yang, Y. L.; Chao, D. M.; Lazarus, L. H.; Xia, Y. Curr. Drug Targets 2012, 13, 230.
doi: 10.2174/138945012799201612
Smith, N. J.; Bennett, K. A.; Milligan, G. Mol. Cell. Endocrinol. 2011, 331, 241.
doi: 10.1016/j.mce.2010.07.009
Huang, W. J.; Manglik, A.; Venkatakrishnan, A. J.; Laeremans, T.; Feinberg, E. N.; Sanborn, A. L.; Kato, H. E.; Livingston, K. E.; Thorsen, T. S.; Kling, R.; Granier, S.; Gmeiner, P.; Husbands, S. M.; Trayner, J. R.; Weis, W. I.; Steyaert, J.; Dror, R. O.; Kobilka, B. K. Nature 2015, 524, 315.
doi: 10.1038/nature14886
Fenalti, G.; Giguere, P. M.; Katritch, V.; Huang, X. P.; Thompson, A. A.; Cherezov, V.; Roth, B. L.; Stevens, R. C. Nature 2014, 506, 191.
doi: 10.1038/nature12944
Wu, H. X.; Wacker, D.; Mileni, M.; Katritch, V.; Han, G. W.; Vardy, E.; Liu, W.; Thompson, A. A.; Huang, X. P.; Carroll, F. I.; Mascarella, S. W.; Westkaemper, R. B.; Mosier, P. D.; Roth, B. L.; Cherezov, V.; Stevens, R. C. Nature 2012, 485, 327.
doi: 10.1038/nature10939
Thompson, A. A.; Liu, W.; Chun, E.; Katritch, V.; Wu, H. X.; Vardy, E.; Huang, X. P.; Trapella, C.; Guerrini, R.; Calo, G.; Roth, B. L.; Cherezov, V.; Stevens, R. Nature 2012, 485, 395.
doi: 10.1038/nature11085
Portoghese, P. S.; Sultana, M.; Nagase, H. J. Med. Chem. 1988, 21, 281.
Chang, K. J.; Yi, S. P.; Shen, Y. H. Neural Functions of the Delta-Opioid Receptor, Ed.: Xia, Y., Springer, Switzerland, 2015, pp. 45~65.
Calderon, S. N.; Coop, A. Curr. Pharm. Des. 2004, 10, 733.
doi: 10.2174/1381612043453054
Calderon, S. N. Top. Curr. Chem. 2011, 299, 121.
Bishop, M. J.; McNutt, R. W. The Dela Receptor, Marcel Dekker, New York, Basel, 2004, pp. 113~138.
Chang, K. J.; Rigdon, G. C.; Howard, J. L.; McNutt, R. W. J. Pharmacol. Exp. Ther. 1993, 267, 852.
Calderon, S. N.; Rothman, R. B.; Porreca, F.; Flippen-Anderson, J. L.; McNutt, R. W.; Xu, H.; Smith, L. E.; Bilsky, E. J.; Davis, P.; Rice, K. C. J. Med. Chem. 1994, 37, 2125.
doi: 10.1021/jm00040a002
Watson, M. J.; Holt, J. D. S.; O'Neill, S. J.; Wei, K.; Pendergast, W.; Gross, G. J.; Gengo, P. J.; Chang, K. J. J. Pharmacol. Exp. Ther. 2006, 316, 423.
Su, Y. F.; Mcnutt, R. W.; Chang, K. J. J. Pharmacol. Exp. Ther. 1998, 287, 815.
Marie, N.; Landemore, G.; Debout, C.; Jauzac, P.; Allouche, S. Life Sci. 2003, 73, 1691.
doi: 10.1016/S0024-3205(03)00489-2
Thomas, J. B.; Herault, X. M.; Rothman, R. B.; Atkinson, R. N.; Burgess, J. P.; Mascarella, S. W.; Dersch, C. M.; Xu, H.; Flippen-Anderson, J. L.; George, C. F.; Carroll, F. I. J. Med. Chem. 2001, 44, 972.
doi: 10.1021/jm000427g
Carson, J. R.; Coats, S. J.; Codd, E. E.; Dax, S. L.; Lee, J.; Martinez, R. P.; Neilson, L. A.; Pitis, P. M.; Zhang, S. P. Bioorg. Med. Chem. Lett. 2004, 14, 2109.
doi: 10.1016/j.bmcl.2004.02.051
Liras, S.; McHardy, S. F.; Allen, M. P.; Segelstein, B. E.; Heck, S. D.; Bryce, D. K.; Schmidt, A. W.; Vanase-Frawley, M.; Callegari, E.; McLean, S. Bioorg. Med. Chem. Lett. 2010, 20, 503.
doi: 10.1016/j.bmcl.2009.11.113
Le Bourdonnec, B.; Windh, R. T.; Ajello, C. W.; Leister, L. K.; Gu, M. H.; Chu, G. H.; Tuthill, P. A.; Barker, W. M.; Koblish, M.; Wiant, D. D.; Graczyk, T. M.; Belanger, S.; Cassel, J. A.; Feschenko, M. S.; Brogdon, B. L.; Smith, S. A.; Christ, D. D.; Derelanko, M. J.; Kutz, S.; Little, P. J.; DeHaven, R. N.; DeHaven-Hudkins, D. L.; Dolle, R. E. J. Med. Chem. 2008, 51, 5893.
doi: 10.1021/jm8008986
Le Bourdonnec, B.; Windh, R. T.; Leister, L. K.; Zhou, Q. J.; Ajello, C. W.; Gu, M. H.; Chu, G. H.; Tuthill, P. A.; Barker, W. M.; Koblish, M.; Wiant, D. D.; Graczyk, T. M.; Belanger, S.; Cassel, J. A.; Feschenko, M. S.; Brogdon, B. L.; Smith, S. A.; Derelanko, M. J.; Kutz, S.; Little, P. J.; DeHaven, R. N.; DeHaven-Hudkins, D. L.; Dolle, R. E. J. Med. Chem. 2009, 52, 5685.
doi: 10.1021/jm900773n
Spahn, V.; Stein, C. Expert Opin. Invest. Drugs 2017, 26, 155.
doi: 10.1080/13543784.2017.1275562
Szmuszkovicz, J.; Von Voigtlander, P. F. J. Med. Chem. 1982, 25, 1125.
doi: 10.1021/jm00352a005
DeHaven-Hudkins, D. L.; Dolle, R. E. Curr. Pharm. Des. 2004, 10, 743.
doi: 10.2174/1381612043453036
Shaw, J. S.; Carroll, J. A., Alcock, P.; Main, B. G. Br. J. Pharmacol. 1989, 96, 986.
doi: 10.1111/bph.1989.96.issue-4
Birch, P. J.; Hayes, A. G.; Johnson, M. R.; Lea, T. A.; Murray, P. J.; Rogers, H.; Scopes, D. I. C. Bioorg. Med. Chem. Lett. 1992, 2, 1275.
doi: 10.1016/S0960-894X(00)80229-2
Kramer, H. J.; Uhl, W.; Ladstetter, B.; B cker, A. Br. J. Clin. Pharmacol. 2000, 50, 227.
Kumar, V.; Marella, M. A.; Cortes-Burgos, L.; Chang, A. C.; Cassel, J. A.; Daubert, J. D.; DeHaven, R. N.; DeHaven-Hudkins, D. L.; Gottshall, S. L.; Mansson, E.; Maycock, A. L. Bioorg. Med. Chem. Lett. 2000, 10, 2567.
doi: 10.1016/S0960-894X(00)00519-9
Tuthill, P. A.; Seida, P. R.; Barker, W.; Cassel, J. A.; Belanger, S.; DeHaven, R. N.; Koblish, M.; Gottshall, S. L.; Little, P. J.; DeHaven-Hudkins, D. L.; Dolle, R. E. Bioorg. Med. Chem. Lett. 2004, 14, 5693.
doi: 10.1016/j.bmcl.2004.08.041
Kumar, V.; Guo, D. Q.; Daubert, J. D.; Cassel, J. A.; DeHaven, R. N.; Mansson, E.; DeHaven-Hudkins, D. L.; Maycock, A. L. Bioorg. Med. Chem. Lett. 2005, 15, 1279.
doi: 10.1016/j.bmcl.2005.01.038
Zaveri, N. T. J. Med. Chem. 2016, 59, 7011.
doi: 10.1021/acs.jmedchem.5b01499
Kawamoto, H.; Ozaki, S.; Itoh, Y.; Miyaji, M.; Arai, S.; Nakashima, H.; Kato, T.; Ohta, H.; Iwasawa, Y. J. Med. Chem. 1999, 42, 5061.
doi: 10.1021/jm990517p
Satoh, A.; Sagara, T.; Sakoh, H.; Hashimato, M.; Nakashima, H.; Kato, T.; Goto, Y.; Mizutani, S.; Azuma-Kanoh, T.; Tani, T.; Okuda, S.; Okamoto, O.; Ozaki, S.; Iwasawa, Y.; Ohta, H.; Kawamoto, H. J. Med. Chem. 2009, 52, 4091.
doi: 10.1021/jm900581g
Toledo, M. A.; Pedregal, C.; Lafuente, C.; Diaz, N.; Martinez-Grau, M. A.; Jiménez, A.; Benito, A.; Torrado, A.; Mateos, C.; Joshi, E. M.; Kahl, S. D.; Rash, K. S.; Mudra, D. R.; Barth, V. N.; Shaw, D. B.; McKinzie, D.; Witkin, J. M.; Statnick, M. A. J. Med. Chem. 2014, 57, 3418.
doi: 10.1021/jm500117r
Post, A.; Smart, T. S.; Krikke-Workel, J.; Dawson, G. R.; Harmer, C. J.; Browning, M.; Jackson, K.; Kakar, R.; Mohs, R.; Statnick, M.; Wafford, K.; McCarthy, A.; Barth, V.; Witkin, J. M. Neuropsychopharmacology 2016, 41, 1803.
doi: 10.1038/npp.2015.348
Zaratin, P. F.; Petrone, G.; Sbacchi, M.; Garnier, M.; Fossati, C.; Petrillo, P.; Ronzoni, S.; Giardina, G. A. M.; Scheideler, M. A. J. Pharmacol. Exp. Ther. 2004, 308, 454.
Marti, M.; Mela, F.; Budri, M.; Volta, M.; Malfacini, D.; Molinari, S.; Zaveri, N. T.; Ronzoni, S.; Petrillo, P.; Calò, G.; Morari, M. Br. J. Pharmacol. 2013, 168, 863.
doi: 10.1111/j.1476-5381.2012.02219.x
Fischetti, C.; Camarda, V.; Rizzi, A.; Pelà, M.; Trapella, C.; Guerrini, R.; McDonald, J.; Lambert, D. G.; Salvadori, S.; Regoli, D.; Calò, G. Eur. J. Pharmacol. 2009, 614, 50.
doi: 10.1016/j.ejphar.2009.04.054
Shinkai, H.; Ito, T.; Iida, T.; Yamada, H.; Uchida, I. J. Med. Chem. 2000, 43, 4667.
doi: 10.1021/jm0002073
O'Neill, S. J.; Collins, M. A.; Pettit, H. O.; McNutt, R. W.; Chang, K. J. J. Pharmacol. Exp. Ther. 1997, 282, 271.
Negus, S. S.; Gatch, M. B.; Mello, N. K.; Zhang, X. Y.; Rice, K. J. Pharmacol. Exp. Ther. 1998, 286, 362.
Lee, P. H. K.; Mcnutt, R. W.; Chang, K. J. J. Pharmacol. Exp. Ther. 1993, 267, 883.
Lahti, R. A.; Vonvoigtlander, P. F.; Barsuhn, C. Life Sci. 1982, 31, 2257.
doi: 10.1016/0024-3205(82)90132-1
Schenk, S.; Partridge, B. Pharmacol. Biochem. Behav. 2001, 68, 629.
doi: 10.1016/S0091-3057(00)00478-0
Bishop, M. J.; Carrido, D. M.; Boswell, G. E.; Collins, M. A.; Harris, P. A.; McNutt, R. W.; O'Neill, S. J.; Chang, K. J. J. Med. Chem. 2003, 46, 623.
doi: 10.1021/jm020395s
Gengo, P. J.; Chang, K. J. The Dela Receptor, Marcel Dekker, New York, Basel, 2004, pp. 231~244.
Yi, S. P.; Kong, Q. H.; Li, Y. L.; Pan, C. L.; Cui, B. Q.; Wang, Y. F.; Wang, G. L.; Zhou, P. L.; Wang, L. L.; Gong, Z. H.; Su, R. B.; Shen, Y. H.; Yu, G.; Chang, K. J. Acta Pharmacol. Sin. 2017, 38, 977.
doi: 10.1038/aps.2017.14
Li, J. L.; Kong, Q. H.; Yu, J.; Yi, S. P.; Li, Y. M.; Wang, G. L.; Shen, Y. H.; Chang, K. J. Chin. Pharmacol. Bull. 2016, 32, 652(in Chinese).
doi: 10.3969/j.issn.1001-1978.2016.05.012
Yu, G.; Li, S. H.; Cui, M. X.; Yan, L. D.; Yong, Z.; Zhou, P. L.; Su, R. B.; Gong, Z. H. CNS Neurosci. Ther. 2014, 20, 282.
doi: 10.1111/cns.2014.20.issue-3
Linz, K.; Christoph, T.; Tzschentke, T. M.; Koch, T.; Schiene, K.; Gautrois, M.; Schröder, W.; Kögel, B. Y.; Beier, H.; Englberger, W.; Schunk, S.; De Vry, J.; Jahnel, U.; Frosch, S. J. Pharmacol. Exp. Ther. 2014, 349, 535.
doi: 10.1124/jpet.114.213694
Ananthan, S.; Khare, N. K.; Saini, S. K.; Seitz, L. E.; Bartlett, J. L.; Davis, P.; Dersch, C. M.; Porreca, F.; Rothman, R. B.; Bilsky, E. J. J. Med. Chem. 2004, 47, 1400.
doi: 10.1021/jm030311v
Ananthan, S.; Saini, S. K.; Dersch, C. M.; Xu, H.; McGlinchey, N.; Giuvelis, D.; Bilsky, E. J.; Rothman, R. B. J. Med. Chem. 2012, 55, 8350.
doi: 10.1021/jm300686p
Healy, J. R.; Bezawada, P.; Shim, J.; Jones, J. W.; Kane, M. A.; MacKerell, A. D. Jr.; Coop, A.; Matsumoto, R. R. ACS Chem. Neurosci. 2013, 4, 1256.
doi: 10.1021/cn4000428
Breslin, H. J.; Diamond, C. J.; Kavash, R. W.; Cai, C. Z.; Dyatkin, A. B.; Miskowski, T. A.; Zhang, S. P.; Wade, P. R.; Hornby, P. J.; He, W. Bioorg. Med. Chem. Lett. 2012, 22, 4869.
doi: 10.1016/j.bmcl.2012.05.042
Levy-Cooperman, N.; McIntyre, G.; Bonifacio, L.; McDonnell, M.; Davenport, J. M.; Covington, P. S.; Dove, L. S.; Sellers, E. M. J. Pharmacol. Exp. Ther. 2016, 359, 471.
doi: 10.1124/jpet.116.236547
Link, A.; Müller, C. E. Angew. Chem., Int. Ed. 2016, 55, 15962.
doi: 10.1002/anie.201609015
Pradhan, A. A.; Smith, M. L.; Kieffer, B. L.; Evans, C. J. Br. J. Pharmacol. 2012, 167, 960.
doi: 10.1111/j.1476-5381.2012.02075.x
Chen, X. T.; Pitis, P.; Liu, G. D.; Yuan, C.; Gotchev, D.; Cowan, C. L.; Rominger, D. H.; Koblish, M.; DeWire, S. M.; Crombie, A. L.; Violin, J. D.; Yamashita, D. S. J. Med. Chem. 2013, 56, 8019.
doi: 10.1021/jm4010829
DeWire, S. M.; Yamashita, D. S.; Rominger, D. H.; Liu, G. D.; Cowan, C. L.; Graczyk, T. M.; Chen, X. T.; Pitis, P. M.; Gotchev, D.; Yuan, C.; Koblish, M.; Lark, M. W.; Violin, J. D. J. Pharmacol. Exp. Ther. 2013, 344, 708.
doi: 10.1124/jpet.112.201616
Manglik, A.; Lin, H.; Aryal, D. K.; McCorvy, J. D.; Dengler, D.; Corder, G.; Levit, A.; Kling, R. C.; Bernat, V.; Hübner, H.; Huang, X. P.; Fassano, M. F.; Giguère, P. M.; Löber, S.; Duan, D.; Scherrer, G.; Kobilka, B.; Gmeiner, P.; Roth, B. L.; Shoichet, B. K. Nature 2016, 537, 185.
doi: 10.1038/nature19112
Váradi, A.; Marrone, G. F.; Palmer, T. C.; Narayan, A.; Szabó, M. R.; Le Rouzic, V.; Grinnell, S. G.; Subrath, J. J.; Warner, E.; Kalra, S.; Hunkele, A.; Pagirsky, J.; Eans, S. O.; Medina, J. M.; Xu, J.; Pan, Y. X.; Borics, A.; Pasternak, G. W.; McLaughlin, J. P.; Majumdar, S. J. Med. Chem. 2016, 59, 8381.
doi: 10.1021/acs.jmedchem.6b00748
Liu, X.; Zhao, L.; Wang, Y.; Zhou, J. J.; Wang, D.; Zhang, Y. X.; Zhang, X. H.; Wang, Z. J.; Yang, D. X.; Mou, L. Y.; Wang, R. ACS Chem. Neurosci. 2017, 8, 2180.
doi: 10.1021/acschemneuro.7b00097
Xiuya Ma , Yu Chen , Yan Zhang . Stories about Pharmaceuticals. University Chemistry, 2025, 40(7): 232-240. doi: 10.12461/PKU.DXHX202408003
Peng Zhan . Practice and Reflection in Training Medicinal Chemistry Graduate Students. University Chemistry, 2024, 39(6): 112-121. doi: 10.3866/PKU.DXHX202402022
Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
Ziheng Zhuang , Xiao Xu , Kin Shing Chan . Superdrugs for Superbugs. University Chemistry, 2024, 39(9): 128-133. doi: 10.3866/PKU.DXHX202309040
Peihong Fan , Hongxiang Lou . 研究生高等天然药物化学课程的教学改革探索——导学互促式混合课堂教学与自主学习能力培养. University Chemistry, 2025, 40(6): 16-21. doi: 10.12461/PKU.DXHX202407078
Zhibei Qu , Changxin Wang , Lei Li , Jiaze Li , Jun Zhang . Organoid-on-a-Chip for Drug Screening and the Inherent Biochemistry Principles. University Chemistry, 2024, 39(7): 278-286. doi: 10.3866/PKU.DXHX202311039
Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
Zheqi Wang , Yawen Lin , Shunliu Deng , Huijun Zhang , Jinmei Zhou . Antiviral Strategies: A Brief Review of the Development History of Small Molecule Antiviral Drugs. University Chemistry, 2024, 39(9): 85-93. doi: 10.12461/PKU.DXHX202403108
Xiaoxuan Yu , Wukun Liu . Practice of Ideological and Political Education in Medicinal Chemistry for Pharmacy Administration Major: A Case Study on the Discovery of Cisplatin’s Anticancer Function. University Chemistry, 2025, 40(4): 408-414. doi: 10.12461/PKU.DXHX202405200
Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
Jinghua Wang , Yanxin Yu , Yanbiao Ren , Yesheng Wang . Integration of Science and Education: Investigation of Tributyl Citrate Synthesis under the Promotion of Hydrate Molten Salts for Research and Innovation Training. University Chemistry, 2024, 39(11): 232-240. doi: 10.3866/PKU.DXHX202402057
Zhao Lu , Hu Lv , Qinzhuang Liu , Zhongliao Wang . Modulating NH2 Lewis Basicity in CTF-NH2 through Donor-Acceptor Groups for Optimizing Photocatalytic Water Splitting. Acta Physico-Chimica Sinica, 2024, 40(12): 2405005-. doi: 10.3866/PKU.WHXB202405005
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
Yiming Liang , Ziyan Pan , Kin Shing Chan . One Drink, Two Tears in the Central Nervous System: The Perils of Disulfiram-Like Reactions. University Chemistry, 2025, 40(4): 322-325. doi: 10.12461/PKU.DXHX202406016
Jiarui Wu , Gengxin Wu , Yan Wang , Yingwei Yang . Crystal Engineering Based on Leaning Towerarenes. University Chemistry, 2024, 39(3): 58-62. doi: 10.3866/PKU.DXHX202304014
Zongfei YANG , Xiaosen ZHAO , Jing LI , Wenchang ZHUANG . Research advances in heteropolyoxoniobates. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 465-480. doi: 10.11862/CJIC.20230306
Shitao Fu , Jianming Zhang , Cancan Cao , Zhihui Wang , Chaoran Qin , Jian Zhang , Hui Xiong . Study on the Stability of Purple Cabbage Pigment. University Chemistry, 2024, 39(4): 367-372. doi: 10.3866/PKU.DXHX202401059
Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
Jing Yan , Haiyuan Wang , Jing Chang , Fubao Xing , Zhen Zhang , Mingyue Chen , Xiaofeng Li , Yu Liu , Yi Li , Xia Feng . Exploration and Practice in the Teaching of Chemistry Research Training Course. University Chemistry, 2024, 39(10): 236-241. doi: 10.12461/PKU.DXHX202404108
Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024