Twin and triplet drugs in opioid research

Topics in Current Chemistry

Volumn 299, Issue , 2011, Pages 239-275

  Fujii, Hideaki ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

Dual action; Increment of potency; Receptor dimerization; Triplet drug; Twin drug

Indexed keywords

NARCOTIC ANALGESIC AGENT; OPIATE RECEPTOR;

ANIMAL; ARTICLE; CHEMISTRY; HUMAN; PROTEIN MULTIMERIZATION; SYNTHESIS;

ANALGESICS, OPIOID; ANIMALS; HUMANS; PROTEIN MULTIMERIZATION; RECEPTORS, OPIOID;

EID: 79551471701     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_2010_76     Document Type: Article

References (166)

1. Contreras J-M, Sippl W (2008) In: Wermuth CG (ed)) The practice of medicinal chemistry, 3rd edn. Academic, Amsterdam, pp 380-414
2. Hazum E, Chang K-J, Cuatrecasas P (1979) Science 206:1077
3. Portoghese PS, Larson DL, Sayre LM, Yim CB, Ronsisvalle G, Tam SW, Takemori AE (1986) J Med Chem 29:1855
4. Portoghese PS (2001) J Med Chem 44:2259
5. Portoghese PS (1989) Trends Pharmacol Sci 10:230
6. Poetoghese PS (1991) J Med Chem 34:1757
7. Portoghese PS, Lipkowski AW, Takemori AE (1987) J Med Chem 30:238
8. Portoghese PS, Nagase H, Lipkowski AW, Larson DL, Takemori AE (1988) J Med Chem 31:836
9. Portoghese PS, Sultana M, Nagase H, Takemori AE (1988) J Med Chem 31:281
10. Portoghese PS, Sultana M, Takemori AE (1988) Eur J Pharmacol 146:185
11. Portoghese PS, Sultana M, Takemori AE (1990) J Med Chem 33:1714
12. Jordan BA, Devi LA (1999) Nature 399:697
13. Lavac BAR, O'Dowd BF, George SR (2007) Curr Opin Pharmacol 2:76
14. Gomes I, Jordan BA, Gupta A, Trapaidze N, Nagy V, Devi LA (2000) J Neurosci 20:RC110
15. George SR, Fan T, Xie Z, Tse R, Tam V, Varghese G, O'Dowd BF (2000) J Biol Chem 275:26128
16. Gomes I, Gupta A, Filipovska J, Szeto HH, Pintar JE, Devi LA (2004) Proc Nat Acad Sci USA 101:5135
17. Wang D, Sun X, Bohn LM, Sadée W (2005) Mol Pharmacol 67:2173
18. Devi LA (2001) Trends Pharmacol Sci 22:532 and references cited therein
19. George SR, O'Dowd BF, Lee SP (2002) Nature Rev Drug Discov 1:808 and references cited therein
20. Dhawan BN, Cesselin F, Raghubir R, Reisine T, Bradley PB, Portoghese PS, Hamon M (1996) Pharmacol Rev 48:567
21. Sato M, Minami M (1995) Pharmacol Ther 68:343
22. Morphy R, Kay C, Rankovic Z (2004) Drug Discov Today 9:641
23. Morphy R, Rankovic Z (2005) J Med Chem 48:6523
24. Morphy R, Rankovic Z (2008) In: Wermuth CG (ed)) The practice of medicinal chemistry, 3rd edn. Academic, Amsterdam, pp 549-571 and references cited therein
25. Halazy S (1999) Exp Opin Ther Patents 9:431
26. Peng X, Neumeyer JL (2007) Curr Top Med Chem 7:363
27. Dietis N, Guerrini R, Calo G, Salvadori S, Rowbotham DJ, Lambert DG (2009) Br J Anaesth 103:38
28. Ballet S, Pietsch M, Abell AD (2008) Protein Peptide Lett 15:668
29. Schiller PW (2010) Life Sci 86:598
30. Negus SS, Mello NK, Portoghese PS, Lin C-E (1997) J Pharmacol Exp Ther 282:44
31. Mello NK, Negus SS (1998) J Pharmacol Exp Ther 286:812
32. Bowen CA, Negus SS, Zong R, Neumeyer JL, Bidlack JM, Mello NK (2003) Neuropsycho-pharmacology 28:1125
33. Gates M, Montzak TA (1964) J Med Chem 7:129
34. Neumeyer JL, Bidlack JM, Zong R (2000) J Med Chem 43:114
35. Neumeyer JL, Zhang A, Xiong W, Gu X-H, Hilbert JE, Knapp BI, Negus S, Mello NK, Bidlack JM (2003) J Med Chem 46:5162
36. Peng X, Knapp BI, Bidlack JM, Neumeyer JL (2006) J Med Chem 49:256
37. Decker M, Fulton BS, Zhang B, Knapp BI, Bidlack JM, Neumeyer JL (2009) J Med Chem 52:7389
38. Decker M, Si Y-G, Knapp BI, Bidlack JM, Neumeyer JL (2010) J Med Chem 53:402
39. Casy AF, Parfitt RT (1986) Opioid analgesics, chemistry and receptors. Plenum, New York
40. Fries DS (1995) In: Lemke TL, Williams DA (ed)s) Foye's principles of medicinal chemistry, 6th edn. Williams & Wilkins, Philadelphia, pp 652-678
41. Fulton BS, Knapp BL, Bidlack JM, Neumeyer JL (2010) Bioorg Med Chem Lett 20:1507
42. Wentland MP, Albertson NF, Pierson AK (1980) J Med Chem 23:71
43. Hedberg MH, Johansson AM, Fowler CJ, Terenius L, Hacksell U (1994) Bioorg Med Chem Lett 4:2527
44. Kubota H, Rothman RB, Dersch C, McCullough K, Pinto J, Rice KC (1999) Bioorg Med Chem Lett 8:799
45. Wentland MP, Xu G, Cioffi CL, Ye Y, Duan W, Cohen DJ, Colasurdo AM, Bidlack JM (2000) Bioorg Med Chem Lett 10:183
46. McCurdy CR, Jones RM, Portogese PS (2000) Org Lett 2:819
47. Wentland MP, Duan W, Cohen DJ, Bidlack JM (2000) J Med Chem 46:3558
48. Wentland MP, Lou R, Ye Y, Cohen DJ, Richardson GP, Bidlack JM (2001) Bioorg Med Chem Lett 11:623
49. Wentland MP, Lou R, Dehnhardt CM, Duan W, Cohen DJ, Bidlack JM (2001) Bioorg Med Chem Lett 11:1717
50. Wentland MP, Ye Y, Cioffi CL, Lou R, Zhou Q, Xu G, Duan W, Dehnhardt CM, Sun X, Cohen DJ, Bidlack JM (2003) J Med Chem 46:838
51. Zhang A, Xiong W, Bidlack JM, Hilbert JE, Knapp BI, Wentland MP, Neumeyer JL (2004) J Med Chem 47:165
52. Wentland MP, VanAlstine M, Kucejki R, Lou R, Cohen DJ, Parkhill AL, Bidlack JM (2006) J Med Chem 49:5635
53. Peng X, Knapp BI, Bidlack JM, Neumeyer JL (2007) Bioorg Med Chem Lett 17:1508
54. Peng X, Knapp BI, Bidlack JM, Neumeyer JL (2007) Bioorg Med Chem 15:4106
55. Reden J, Reich MF, Rice KC, Jacobson AE, Brossi A (1979) J Med Chem 22:256
56. Wentland MP, Lu Q, Lou R, Bu Y, Knapp BI, Bidlack JM (2005) Bioorg Med Chem Lett 15:2107
57. Wentland MP, Lou R, Lu Q, Bu Y, VanAlstine MA, Cohen DJ, Bidlack JM (2009) Bioorg Med Chem Lett 19:203
58. Wentland MP, Lou R, Lu Q, Bu Y, Denhardt C, Jin J, Ganorkar R, VanAlstine MA, Guo C, Cohen DJ, Bidlack JM (2009) Bioorg Med Chem Lett 19:2289
59. Portoghese PS, Larson DL, Yim CB, Sayre LM, Ronsisvalle G, Lipkowski AW, Takemori AE, Rice KC, Tam SW (1985) J Med Chem 28:1140
60. Mathews JL, Peng X, Xiong W, Zhang A, Negus SS, Neumeyer JL, Bidlack JM (2005) J Pharmacol Exp Ther 315:821
61. Mathews JL, Fulton BS, Negus SS, Neumeyer JL, Bidlack JM (2008) Neurochem Res 33:2142
62. Reindl JD, Rowan K, Carey AN, Peng X, Neumeyer JL, McLaughlin JP (2008) Pharmacology 81:229
63. Carlezon WA Jr, Béguin C, DiNieri JA, Baumann MH, Richards MR, Todtenkopf MS, Rothman RB, Ma Z, Lee DY-W, Cohen BM (2006) J Pharmacol Exp Ther 316:440
64. McLaughlin JP, Land BB, Li S, Pintar JE, Chavkin C (2006) Neuropsychopharmacology 31:787
65. McLaughlin JP, Marton-Popovici M, Chavkin C (2003) J Neurosci 23:5674
66. Mague SD, Pliakas AM, Todtenkopf MS, Tomasiewicz HC, Zhang Y, Stevens WC Jr, Jones RM, Portoghese PS, Carlezon WA Jr (2003) J Pharmacol Exp Ther 305:323
67. Beardsley PM, Howard JL, Shelton KL, Carroll FI (2005) Psychopharmacology 183:118
68. Salvadori S, Guerrini R, Balboni G, Bianchi C, Bryant SD, Cooper PS, Lazarus LH (1999) J Med Chem 42:5010
69. Neumeyer JL, Peng X, Knapp BI, Bidlack JM, Lazarus LH, Salvadori S, Trapella C, Balboni G (2006) J Med Chem 49:5640
70. Peng X, Knapp BI, Bidlack JM, Neumeyer JL (2007) J Med Chem 50:2254
71. Sayre LM, Portoghese PS (1980) J Org Chem 45:3366
72. Jones RM, Hjorth JRM, Schwartz TW SA, Portoghese PS (1998) J Med Chem 41:4911
73. Jones RM, Portoghese PS (2000) Eur J Pharmacol 396:49
74. Zhang S, Yekkirala A, Tang Y, Portoghese PS (2009) Bioorg Med Chem Lett 19:6978
75. Portoghese PS, Sultana M, Nelson WL, Klein P, Takemori AE (1992) J Med Chem 35:4086
76. Poss MA, Iwanowicz E, Reid JA, Lin J, Gu Z (1992) Tetrahedron Lett 33:5933
77. Kim KY, Qian L (1993) Tetrahedron Lett 34:7677
78. Garzon J, Juarros JL, Castro MA, Sanchez-Blazquez P (1995) Mol Pharmacol 47:738
79. Wessendorf MW, Dooyema J (2001) Neurosci Lett 298:151
80. Portoghese PS, Lunzer MM (2003) Eur J Pharmacol 467:233
81. Bhushan RG, Sharma SK, Xie Z, Daniels DJ, Portoghese PS (2004) J Med Chem 47:2969
82. Mosberg HI, Hurst R, Hurby VJ, Gee K, Yamamura HI, Galligan JJ, Burks TF (1983) Proc Natl Acad Sci USA 80:5871
83. Nock B (1995) In: Tseng LF (ed)) The pharmacology of opioid peptides. Harwood Academic Publishers, Singapore, pp 29-56
84. Simonin F, Slowe S, Becker JAJ, Matthes HWD, Filliol D, Chluba J, Kitchen I, Kieffer BL (2001) Eur J Pharmacol 414:189
85. Erspamer V, Melchiorri P, Falconieri-Erspamer G, Negri L, Corsi R, Severini C, Barra D, Simmaco M, Kreil G (1989) Proc Natl Acad Sci USA 86:5188
86. Szmuszkovicz J, Von Voigtlander PF (1982) J Med Chem 25:1125
87. Xie Z, Bhushan RG, Daniels DJ, Portoghese PS (2005) Mol Pharmacol 68:1079
88. Barlow JJ, Blackburn TP, Costello GF, James J, Le Count DJ, Main BG, Pearce RJ, Russel K, Shaw JS (1991) J Med Chem 34:3149
89. Daniels DJ, Kulkarni A, Xie Z, Bhushan RG, Portoghese PS (2005) J Med Chem 48:1713
90. Sofuoglu M, Portoghese PS, Takemori AE (1991) J Pharmacol Exp Ther 257:676
91. Portoghese PS, Nagase H, MaloneyHuss KE, Lin C-E, Takemori AE (1991) J Med Chem 34:1715
92. Portoghese PS, Sultana M, Nagase H, Takemori AE (1992) Eur J Pharmacol 218:195
93. Ohkawa S, Portoghese PS (1998) J Med Chem 41:4177
94. Nock B, Giordano AL, Cicero TJ, O'Connor LH (1990) J Pharmacol Exp Ther 254:412
95. Vaught JL, Takemori A (1979) J Pharmacol Exp Ther 208:86
96. Vaught JL, Rothman RB, Westfall TC (1982) Life Sci 30:1443
97. Miyamoto Y, Portoghese PS, Takemori AE (1993) J Pharmacol Exp Ther 264:1141
98. Abdelhamid EE, Sultana M, Portoghese PS, Takemori AE (1991) J Pharmacol Exp Ther 258:299
99. Miyamoto Y, Brown WD, Portoghese PS, Takemori AE (1994) J Pharmacol Exp Ther 270:37
100. Fundytus ME, Schiller PW, Shapiro M, Weltrowska G, Coderre TJ (1995) Eur J Pharmacol 286:105
101. Daniels DJ, Lenard NR, Etienne CL, Law P-Y, Roerig SC, Portoghese PS (2005) Proc Natl Acad Sci USA 102:19208
102. Lenard NR, Daniels DJ, Portoghese PS, Roerig SC (2007) Eur J Pharmacol 566:75
103. Nagase H, Kawamura K, Mizusuna A, Fujii H, Nakatani I (2002) JP 2002332284A
104. Fujii H, Watanabe A, Nemoto T, Narita M, Miyoshi K, Nakamura A, Suzuki T, Nagase H (2009) Bioorg Med Chem Lett 19:438
105. Nagase H, Watanabe A, Nemoto T, Yamamoto N, Osa Y, Sato N, Yoza K, Kai T (2007) Tetrahedron Lett 48:2547
106. Fujii H, Nagase H (2006) Curr Med Chem 13:1109
107. Foran SE, Carr DB, Lipkowski AW, Maszczynska I, Marchand JE, Misicka A, Beinborn M, Kopin AS, Kream RM (2000) J Pharmacol Exp Ther 295:1142
108. Foran SE, Carr DB, Lipkowski AW, Maszczynska I, Marchand JE, Misicka A, Beinborn M, Kopin AS, Kream RM (2000) Proc Natl Acad Sci USA 97:7621
109. Bonney IM, Foran SE, Marchand JE, Lipkowski AW, Carr DB (2004) Eur J Pharmacol 488:91
110. Yamamoto T, Nair P, Davis P, Ma S-W, Navratilova E, Moye S, Tumati S (2007) J Med Chem 50:2779
111. Yamamoto T, Nair P, Vagner J, Largent-Milnes T, Davis P, Ma S-W, Navratilova E (2008) J Med Chem 51:1369
112. Yamamoto T, Nair P, Jacobsen NE, Davis P, Ma S-W, Navratilova E, Moye S (2008) J Med Chem 51:6334
113. Hurby VJ, Agnes RS, Davis P, Ma S-W, Lee YS, Vanderah TW, Lai J, Porreca F (2003) Life Sci 73:699
114. Lee YS, Agnes RS, Badghisi H, Davis P, Ma S-W, Lai J, Porreca F, Hruby VJ (2006) J Med Chem 49:1773
115. Ndungu JM, Cain JP, Davis P, Ma S-W, Vanderah TW, Lai J, Porreca F, Hruby VJ (2006) Tetrahedron Lett 47:2233
116. Agnes RS, Lee YS, Davis P, Ma S-W, Badghisi H, Porreca F, Lai J, Hruby VJ (2006) J Med Chem 49:2868
117. Lee YS, Agnes RS, Davis P, Ma S-W, Badghisi H, Lai J, Porreca F, Hruby VJ (2007) J Med Chem 50:165
118. Anges RS, Ying J, Kövér KE, Lee YS, Davis P, Ma S-W, Badghisi H, Porreca F, Lai J, Hruby VJ (2008) Peptides 29:1413
119. Vagner J, Xu L, Handl HL, Josan JS, Morse DL, Mash EA, Gillies RJ, Hruby VJ (2008) Angew Chem Int Ed 47:1685
120. Dardonville C, Rozas I (2004) Med Res Rev 24:639
121. Sánchez-Blázquez P, Boronat MA, Olmos G, Garć?a-Sevilla JA, Garzón J (2000) Br J Pharmacol 130:146
122. Fairbanks CA, Posthumus IJ, Kitto KF, Stone LS, Wilcox GL (2000) Pain 84:13
123. Boronat MA, Olmos G, Garć?a-Sevilla JA (1998) Br J Pharmacol 125:175
124. Boronat MA, Olmos G, Garć?a-Sevilla JA (1999) Ann NY Acad Sci 881:359
125. Ruiz-Durántez E, Torrecilla M, Pineda J, Ugedo L (2003) Br J Pharmacol 138:494
126. Morgan AD, Campbell UC, Fons RD, Carroll ME (2002) Pharmacol Biochem Behav 72:873
127. Rui-Bin SU, Jin LI, Bo-Yi QIN (2003) Acta Pharmacol Sin 24:631
128. Miralles A, Esteban S, Sastre-Coll A, Moranta D, Asensio VJ, García-Sevilla JA (2005) Eur J Pharmacol 518:234
129. Montero A, Goya P, Jagerovic N, Callado LF, Meana JJ, Girón R, Goicoechea C, Martín MI (2002) Bioorg Med Chem 10:1009
130. Li G, Regunathan S, Barrow CJ, Eshraghi J, Cooper R, Reis DJ (1994) Science 263:966
131. Dardonville C, Jagerovic N, Callado LF, Meana JJ (2004) Bioorg Med Chem Lett 14:491
132. Dardonville C, Fernandez-Fernandez C, Gibbons S-L, Ryan GJ, Jagerovic N, Gabilondo AM, Meana JJ, Callado LF (2006) Bioorg Med Chem 14:6570
133. Diaz A, Mayet S, Dickenson AH (1997) Eur J Pharmacol 333:9
134. Lamotte C, Pert CB, Snyder SH (1976) Brain Res 112:407
135. Hökfelt T, Elde R, Johansson O, Terenius L, Stein L (1977) Neurosci Lett 5:25
136. Go VL, Yaksh TL (1987) J Physiol 391:141
137. Duggan AW, Hendry IA, Morton CR, Hutchinson WD, Zhao ZQ (1988) Brain Res 451:261
138. Kar S, Quirion R (1995) J Comp Neurol 354:253
139. Minami M, Maekawa K, Yabuuchi K, Satoh M (1995) Mol Brain Res 30:203
140. Kream RM, Kato T, Shimonaka H, Marchand JE, Wurm WH (1993) Proc Natl Acad Sci USA 90:3564
141. Maszczynska I, Lipkowski AW, Carr DB, Kream RM (1998) Analgesia 3:1
142. Kream RM, Liu N-J, Zhuang M, Esposito PL, Esposito TR, Stefano GB, Witmeyer JJ III (2007) Med Sci Monit 13:BR25
143. Akbarzadeh A, Mehraby M, Zarbakhsh M, Farzaneh H (1999) Biotechnol Appl Biochem 30:139
144. Itoh S, Katsuura G, Maeda Y (1982) Eur J Pharmacol 80:421
145. Faris PL, Komisaruk BP, Watkins LR, Mayer DJ (1983) Science 219:310
146. Wiesinfeld-Hallin Z, Lucas GA, Alster P, Xu X-J, Hokfelt T (1999) Brain Res 848:78
147. Watkins LR, Kinscheck IB, Mayer DJ (1984) Science 224:395
148. Suberg SN, Culhane ES, Carstens E, Watkins LR (1985) Ann NY Acad Sci 448:660
149. Lu L, Huang M, Liu A, Ma L (2000) Neuroreport 11:829
150. Bock MG, DiPardo RM, Evans BE, Rittle KE, Whitter WL, Garsky VM, Gilbert KF, Leighton JL, Carson KL, Mellin EC, Veber DF, Chang RSL, Lotti VJ, Freedman SB, Smith AJ, Patel S, Anderson PS, Freidiner RM (1993) J Med Chem 36:4276
151. Zheng Y, Akgün E, Harikumar KG, Hopson J, Powers MD, Lunzer MM, Miller LJ, Portoghese PS (2009) J Med Chem 52:247
152. Gomes I, Filipovska J, Devi LA (2003) In: Pan ZZ (ed)) Opioid research, methods and protocols. Humana, Totowa, pp 165-170
153. Reider PJ, Davis P, Huges DL, Grabowski EJJ (1987) J Org Chem 52:955
154. Bock MG, Dipardo RM, Evans BE, Rittle KE, Veber DF, Freidinger RM, Hirshfield J, Sringer JP (1987) J Org Chem 52:3232
155. Vardanyan R, Vijay G, Nichol GS, Liu L, Kumarasinghe I, Davis P, Vanderah T, Porreca F, Lai J, Hruby VJ (2009) Bioorg Med Chem 17:5044
156. Shao L, Wang F, Hewitt MC, Barberich TJ (2009) Bioorg Med Chem Lett 19:5679
157. Mathew SC, Ghosh N, By Y, Berthault A, Virolleaud M-A, Carrega L, Chouraqui G, Commeiras L, Condo J, Attolini M, Gaudel-Siri A, Ruf J, Parrain J-L, Rodriguez J, Guieu R (2009) Bioorg Med Chem Lett 19:6736
158. O'Brien JG, Gibson F (1970) Biochim Biophys Acta 215:393
159. Pollack JR, Neilands JB (1970) Biochem Biophys Res Commun 38:989
160. Brockmann H, Schmidt-Kastner G (1955) Chem Ber 88:57
161. Nagase H, Watanabe A, Harada M, Nakajima M, Hasebe K, Mochizuki H, Yoza K, Fujii H (2009) Org Lett 11:539
162. Watanabe A, Fujii H, Nakajima M, Hasebe K, Mochizuki H, Nagase H (2009) Bioorg Med Chem Lett 19:2416
163. Kerns EH, Di L (2008) Drug-like properties: concepts, structure design and methods: from ADME to toxicity optimization. Academic, New York, pp 37-42
164. Kerns EH, Di L (2008) Drug-like properties: concepts, structure design and methods: from ADME to toxicity optimization. Academic, New York, pp 122-136
165. Van Rijn RM, Whistler JL (2009) Biol Psychiatry 66:777
166. Lipkowski AW, Konecka AM, Sroczyńska I (1982) Peptides 3:697