New prospects for glycopeptide based analgesia: Glycoside-induced penetration of the Blood-Brain Barrier

Current Drug Delivery

Volumn 2, Issue 1, 2005, Pages 59-73

  Dhanasekaran, Muthu ^a   Polt, Robin ^a  

^a University of Arizona   (United States)

Author keywords

Analgesia; Blood Brain Barrier; Enkephalin; Glycopeptide; Morphine; Opioid; Transcytosis

Indexed keywords

ADAMANTANE DERIVATIVE; ANTINOCICEPTIVE AGENT; BETA ENDORPHIN; DELTA OPIATE RECEPTOR; DELTORPHIN; DERMORPHIN; DYNORPHIN; DYNORPHIN A [1-8][1 (N METHYLTYROSINE) 7 (N METHYLARGININE) 8 DEXTRO LEUCINE N ETHYLAMIDE]; ENDOMORPHIN 1; ENDOMORPHIN 2; ENDORPHIN; ENKEPHALIN; ENKEPHALIN DERIVATIVE; ENKEPHALIN[2 DEXTRO ALANINE 5 DEXTRO LEUCINE]; ENKEPHALIN[2,5 DEXTRO PENICILLAMINE]; GLUCOSIDE; GLYCOPEPTIDE; KAPPA OPIATE RECEPTOR; LEUCINE ENKEPHALIN; LEUCINE ENKEPHALIN[2 DEXTRO ALANINE 6 ARGININE]; METENKEPHALIN; MORPHICEPTIN; MORPHINE; MORPHINE 6 GLUCURONIDE; MU OPIATE RECEPTOR; MU OPIATE RECEPTOR AGONIST; NANOPARTICLE; NOCICEPTIN; OPIATE; OPIATE PEPTIDE; OPIATE RECEPTOR;

AMINO ACID SEQUENCE; ANALGESIA; ANTINOCICEPTION; BLOOD BRAIN BARRIER; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG MECHANISM; DRUG PENETRATION; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STABILITY; DRUG TRANSPORT; ENZYME DEGRADATION; GLYCOSYLATION; HUMAN; NONHUMAN; PAIN; PRIORITY JOURNAL; PROTEIN MOTIF; REVIEW; TRANSCYTOSIS;

ADJUVANTS, PHARMACEUTIC; ANALGESICS; ANIMALS; BLOOD-BRAIN BARRIER; CHEMISTRY, PHARMACEUTICAL; GLYCOPEPTIDES; GLYCOSIDES;

EID: 17844372759     PISSN: 15672018     EISSN: None     Source Type: Journal    
DOI: 10.2174/1567201052772843     Document Type: Review

References (153)

1. (a) Kririkos, P.G.; Papadaki, S. J. Am. Pharm. Assn. 1968 8, 446-447.
2. (b) Wright, A.D. Trans. Coll. Physicians Phila. 1961, 29 (July), 22-27.
3. (c) The History of Opium and Its Derivatives in Advances in Pain Research and Therapy, Vol. 14, Benedetti, C., Ed.;, Raven Press, New York, 1990, Chapter 1, pp. 1-35,
4. c) http://opioids.com/timeline/.
5. Brownstein, M.J. Proc. Natl. Acad. Sci. USA 1993, 90, 5391-5393.
6. th Edition, Hardman, J.G.; Limbird, L.E.; Gilman, A.G., Eds.; R.R. Donnelley and Sons, New York, 2001, Chapter 23, pp. 569-620.
7. Hannon, J.P.; Bossone, C.A. Am. J. Physiol. 1991, 261, R1286-93.
8. Shavit, Y.; Epaulis, A.; Martin, R.C.; Terman, G.W.; Pechnick, R.N.; Zane, C.J.; Gale, R.P.; Liebeskind, J.C. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 7114-7.
9. (b) Weber, R.J.; Pert, A. Science 1989, 245, 188-190.
10. (c) Carr, D.J.J.; Serou, M. Immunopharm. 1995, 31, 59-71.
11. (d) Gaveriaux, R.C.; Matthes, H.W.D.; Kieffer, B.L. Proc. Natl Acad. Sci. U.S.A. 1998; 95, 6326-6330.
12. (e) Ni, X.; Gritman, K.R.; Eisenstein, T.K.; Adler, M.W.; Arfors, K.E.; Tuma, R.F. Microvasc. Res. 2000, 60, 121-30.
13. McNally, G.P.; Akil, H. In Neuropsychopharmacology: the Fifth Generation of Progress, Davis, K.L.; Charney, D.; Coyle, J.T.; Nemeroff, C. Eds, Lippincott Williams & Wilkins, Philadelphia, 2002, Chapter 3, pp. 35-46.
14. Pert, C.A.; Snyder, S.H. Science 1973, 179, 1011-1014.
15. (b) Simon, E.J.; Hiller, J.M.; Edelman, I. Proc. Natl. Acad. Sci. USA. 1973, 70, 1947-1951.
16. (c) Terenius, L. Acta Pharmacol Toxicol 1973, 32, 317-320.
17. Kosterlitz, H,W.; Lord, J.A.H.; Paterson, S.J.; Waterfield, A.A. Br. J. Pharmacol. 1980, 68, 333-342.
18. Tseng, L.F. Trends in Pharm. Sci. 2001, 22, 623-630.
19. Sufuoglu, M.; Portoghese, P.S.; Takemori, A.E. J. Pharmacol. Exp. Ther. 1991, 257, 676-680.
20. b) Clark, J.A.; Liu, L.; Price, M.; Hersh, B.; Edelson, M.; Paternak, G.W. J. Pharmacol. Exp. Ther. 1989, 251, 461-468.
21. a) Kieffer, B.L.; Befort, K.; Gaveriaus-Ruff, C.; Hirth, C.G. Proc. Natl. Acd. Sci. 1992, 89, 12048-52.
22. b) Evans, C.J.; Keith, D.E.; Morrison, H.; Magendzo, K.; Edwards, R.H. Science 1992, 258, 1952-55.
23. a) Fukuda, K.; Kato, S.; Mori, K.; Nishi, M.; Takeshima, H. FEBS Lett. 1993, 327, 311-14.
24. b) Chen, Y.; Mesick, A.; Liu, J.; Hurley, I.A.; Yu, L. Mol. Pharmacol. 1993, 44, 8-12.
25. a) Yasuda, K.; Raynor, K.; Kong, H.; Breder, C.; Takeda, J.; Reisine, T.; Bell, G.I. Proc. Natl. Acad. Sci. 1993, 90, 6736-40.
26. b) Minami, M.; Toya, T.; Kaao, Y.; Maekawa, K.; Nakamura, S.; Onogi, T. Febs Lett. 1993, 329, 291-95.
27. Pasternak, G.W. Neuroscientist 2001, 7, 220-231.
28. Gaveriaux-Ruff, C.; Kieffer, B.L. Neuropeptides 2002, 36, 62-71.
29. Gomes, I.; Filipovska, J.; Jordan, B.A., Devi, L.A. Methods 2002, 27, 358-365.
30. Chaturvedi, K.; Christoffers, K.H.; Singh, K.; Howells, R.D. Biopolymers 2000, 55, 334-346.
31. Hughes, J.; Smith, T.W.; Kosterlitz, H.W.; Fothergill, L.A.; Morgan, B.A.; Morris, H.R. Nature (London) 1975, 258, 577-579.
32. a) Janecka, A.; Fichna, J.; Janecki, T. Curr. Top. Med. Chem. 2004, 4, 1-17.
33. b) Lipkowski, A.W.; Misicka, A.; Hruby, V.J.; Carr, D.B. Pol. J. Chem. 1994, 68, 907-912.
34. c) Dooley Ct, Chung, N.N.; Wilkes, B.C.; Schiller, P.W.; Bidlack, J.M.; Pasternak, G.W.; Houghten R.A. Science 1994, 266, 2019-2022.
35. Horvat, S. Curr. Med. Chem.: Central Nervous System Agents 2001, 1(2), 133-154.
36. Pardridge, W.M. Brain Drug Targeting. Cambridge University Press: Cambridge, 2001.
37. th Edition. Hardman, J.G.; Limbird, L.E.; Gilman, A.G., Eds.; R.R. Donnelley and Sons, New York, 2001, Chapter 23, pp. 569-619.
38. Höllt, V. Annu. Rev. Pharmacol. Toxicol. 1986, 26, 59-77.
39. Bunzow, J.R.; Saez, C.; Mortrud, M. FEBS Lett. 1994, 347, 279-282.
40. a) Meunier, J.C.; Mollereau, C.; Toll, L. Nature 1995, 377, 532-535.
41. b) Pan, Y,X.; Xu, J.; Pasternak, G.W. Biochem. J. 1996, 315, 11-13.
42. Quirion, R.; Weiss, A.S.. Peptides 1983, 4, 445-452.
43. Loh, H.H.; Tseng, L.F.; Wei, E.; Li, C.J. Proc. Natl. Acad. Sci. USA 1976, 73, 2895.
44. Zadina, J.E.; Hackler, L.; Ge, L-J.; Kastin, A.J. Nature 1997, 386, 499-502.
45. Goldstein, A.; Tachibana, S.; Lowney, L.I.; Hunkapiller, M.; Hood, L. Proc. Natl. Acad. Sci. 1979, 76, 6666-6670.
46. Erspamer, V.; Melchiorri, P.; Falconeri-Erspamer, G.; Negri, L.; Corsi, R.; Severini, C.; Barra, D.; Simmaco, M.; Kriel, G. Proc. Natl. Acad. Sci. 1989, 86, 5188-5192.
47. a) Brantl, V.; Teshemacher, H.; Henschen, A.; Lottspeich, F., Hoppe-Seylers, Z. Physiol. Chem. 1919, 360, 1211-1216.
48. b) Fukudome, S.; Yoshikawa, M. FEBS Lett. 1992, 296, 107-111.
49. c) Fukudome, S.; Yoshikawa, M. FEBS Lett. 1993, 316, 17-19.
50. d) Zadina, J.E.; Kastin, A.J.; Kersh, D.; Wyatt, A. Life Sci. 1992, 51, 869.
51. e) Yunden, J.; Yoshikawa, M. Peptides 1999, 20, 957-962.
52. Yan, S.; Yunden, J.; Sonoda, S.; Doyama, N.; Lipkowski, A.W.; Kawamura, Y.; Yoshikawa, M. FEBS Lett. 2001, 509, 213-217.
53. Gentilucci, L. Curr. Top. Med. Chem. 2004, 4, 19-38.
54. Adessi, C.; Soto, C. Current Med. Chem. 2002, 9, 963-978.
55. Schiller, P.W.; Nguyen; T.M-D.; Maziak, L.; Lemieux C. Biochem. Biophys. Res. Commun. 1985, 127, 558-564.
56. Mosberg, H.I.; Hurst, R.; Hruby, V.J.; Gee, K.; Yamamura, H.I.; Galligan, J.J.; Burks, T.F. Proc. Natl. Acad. Sci. USA. 1983, 80, 5871-5874.
57. Svensson, C.I.; Rew, Y.; Malkmus, S.; Schiller, P.W.; Taulane, J.P.; Goodman, M.; Yaksh, L. J. Pharm. Exp. Ther. 2003, 304, 827-832.
58. (a) Hruby, V.J.; Gehrig, C.A. Med. Res. Rev. 1989, 9, 343-401.
59. (b) Hruby, V.J.; Agnes, R.S. Biopolymers 1999, 51, 391-410.
60. (c) Naqvi, T.; Haq, W.; Mathur, K.B. Peptides 1998, 19, 1277-1292.
61. (a) Handa, B.K.; Lane, A.C.; Lord, J.A.H.; Morgan, B.A.; Rance, M.J.; Smith, C.F.C. Eur. J. Pharmacol. 1981, 70, 531-540.
62. (b) Gacel, G.; Daugé, V.; Breuzé, P.; Delay-Goyet, P.; Roques, B.P. J. Med. Chem. 1988, 31, 1891-1897.
63. (c) Schiller, P.W.; Nguyen, T.M-D.; Weltrowska, G.; Wilkes, B.C.; Marsden, B.J.; Lemieus, C.; Chung, N.N. Proc. Natl. Acad. Sci. USA. 1992, 89, 11871-11875.
64. (d) Schiller, P.W.; Nguyen, T.M-D.; Berezowska, I.; Dupuis, S.; Weltrowska, G.; Chung, N.N.; Lemieux, C. Eur. J. Med. Chem. 2000, 35, 895-901.
65. (a) Shimohigashi, Y.; Kamiya, H.; Costa, T.; Herz, A.; Stammer, C.H. FEBS letters 1988, 233, 289-293.
66. (b) Shimohigashi, Y.; Costa, T.; Nitz, T.J.; Chen, H.C.; Stammer, C.H. Biochem. Biophys. Res. Commun. 1984, 121, 966-972.
67. Schiller, P.W.; Nguyen, T.M.D.; Weltrowska, G.; Wilkes, B.C.; Marsden, B.J.; Lemieux, C.; Chung, N.N. Proc. Natl. Acad. Sci. USA. 1992, 89, 11871-11875.
68. (a) Schiller, P.W.; Fundytus, M.E.; Merovitz, L.; Weltrowska, G.; Nguyen, T.M-D.; Lemieux, C.; Chung, N.N.; Coderre, T.J. J. Med. Chem. 1999, 42, 3520-3526.
69. (b) Neilan, C.L.; Nguyen, T.M-D.; Schiller, P.W.; Pasternak, G.W. Eur. J Pharm. 2001, 419, 15-23.
70. (c) Bryant, S.D.; Jinsmaa, Y.; Salvadori, S.; Okada, Y.; Lazarus, L.H. Biopolymers (Peptide Science) 2003, 71, 86-102.
71. (d) Hruby, V.J.; Balse, P.M. Cur. Med. Chem. 2000, 7, 945-970.
72. Adessi, C.; Soto, C. Cur. Med. Chem. 2002, 9, 963-978.
73. Pardridge, W.M. Introduction to the Blood-Brain Barrier. Cambridge University Press: New York, 1993.
74. Crone, C. Acta Physiol. Scand. 1963, 58, 292-35.
75. Dohrmann, G.J. Brain Res. 1970, 18, 197-218.
76. (a) Pardridge, W.M. Peptide Drug Delivery to the Brain, Raven Press: New York, 1991.
77. (b) de Boer, A.G.; van der Sandt, I.C.J.; Gaillard, P.J. Ann. Rev. Pharmacol. Tox. 2003, 43, 629-656.
78. Breig, N.H.; Fredericks, W.R.; Holoway, H.W.; Soncrant, T.T.; Rapoport, S.I. J. Pharmacol. Exp. Ther. 1988, 245, 581-586.
79. (a) Coffey, R.J.; Burchiel, K. Neurosurgery 2002, 50(1), 78-86.
80. (b) Dahl, J.B.; Jeppesen, I.S.; Jorgensen, H.; Wetterslev, J.; Moiniche, S. Anesthesiology 1999, 91(6), 1919-1927.
81. Egleton, R.D.; Davis, T.P. Peptides 1997, 18, 1431-1439.
82. Vannucci, S.J.; Maher, F.; Simpson, I.A. Glia, 1997, 21, 2-21.
83. Oldendorf, W.H.; Szabo, J. Am. J. Physiol. 1976, 230, 94-98.
84. Maresh, G,A.; Kastin, A.J.; Brown, T.T.; Zadina, J.E.; Banks, W.A. Brain Res. 1999, 839, 336-340.
85. Ermisch, A.; Brust, P.; Kretzschemar, R.; Rühle, H. Physiol Rev. 1993, 73, 489-527.
86. (a) Rapoport, S.I.; Klee, W.A.; Pettigrew, K.D.; Ohno, K. Science 1980, 207, 84-86.
87. (b) Banks, W.A.; Kastin, A.J.; Fischman, A.J.; Coy, D.H.; Strauss, S.L. Am. J. Physiol. 1986, 251, E477-E482.
88. (c) Hauser, M.; Donhardt, A.M.; Barnes, D.; Naider, F.; Becker, J.M. J. Biol. Chem. 2000, 275, 3037-3041.
89. Egleton, R.D.; Abbruscato, T.J.; Thomas, S.A.; Davis, T.P. J. Pharm. Sci. 1998, 87, 1433-1439.
90. Terasaki, T.; Hirai, K.; Sato, H.; Kang, Y-S.; Tsuji, A. J. Pharmacol. Exp. Ther. 1989, 251, 351-357.
91. Deguchi, Y.; Miyakawa, Y.; Sakurada, S.; Naito, Y.; Motimoto, K.; Ohtsuki, S.; Hosoya, K.; Terasaki, T. J. Neurochem. 2003, 84, 1154-1161.
92. (a) Tamai, I.; Sai, Y.; Kobayashi, H.; Kamata, M.; Wakamiya, T.; Tsuji, A. J. Pharmacol. Exp. Ther. 1997, 280, 410-415.
93. (b) Wakamiya, T.; Kamata, M.; Kusummoto, S.; Kobayashi, H.; Sai, Y.; Tamai, I.; Tsuji, A. Bull. Chem. Soc. Jpn. 1998, 78, 699-709.
94. (c) Tsuji, A.; Tamai, I. Adv. Drug Delivery Rev. 1999, 36, 277-290.
95. Temsamani, J.; Rousselle, C.; Rees, A.R.; Scherrmann, J.-M. Vector-mediated drug delivery to the brain. Expert Opinion on Biological Therapy 2001, 1(5), 773-782.
96. Pardridge, W.M. Adv. Drug Delivery Rev. 1995, 15, 109-146.
97. Bodor, N.; Prokai, L.; Wu, W.M.; Farag, H.; Jonalagadda, S.; Kawamura, M.; Simpkins, J. Science 1992, 257, 1698-1700.
98. (a) Wang, b.; Nimkar, K.; wang, W.; Zhang, H.; Shan, D.; Gudmundsson, O.; Gangwar, S.; Siahaan, T.; Borchardt, R.T. J. Pep. Res. 1999, 53, 370-382.
99. (b) Bak, A.; Gudmundsson, O., Friis, G.J.; Siahaan, T.; Borchardt, R.T. J. Pep. Res. 1999, 53, 393-402.
100. (c) Ouyang, H.; Borchardt, R.T.; Siahaan, T.J.; Vander Velde, D. J. Pep. Res. 2002, 59, 183-195.
101. (a) Yang, J.Z.; Chen, W.; Borchardt, R.T. J. Pharmacol. Exp. Ther. 2002, 303, 840-848.
102. (b) Chen, W.; Yang, J.Z.; Anderson, R.; Nielsen, L.H.; Borchardt, R.T. J. Pharmacol. Exp. Ther. 2002, 303, 849-857.
103. Fredholt, K.; Adrian, C.; Just, L.; Larsen, D.H.; Weng, S.; Moss, B.; Friss, G.J. J. Control. Rel. 2000, 63, 261-273.
104. Schroeder, U.; Sommerfeld, P.; Ulrich, S.; Sabel, B.A. J. Pharm. Sci. 1998, 87, 1305-1307.
105. Alyautdin, R.; Gothier, V.; Petrov, V.; Kharkevich, D.; Kreuter, J.; Eur. J. Pharm. Biopharm. 1995, 41, 44-48.
106. Schroeder, U.; Sommerfeld, P.; Sabel, B.A. Peptides 1998, 19, 777-780.
107. Olivier, J.C.; Fenart, L.; Chauvet, R., Pariat, C.; Cecchelli, R.; Couet, W. Pharm. Res. 1999, 16, 1836-1842.
108. Kreuter, J.; Ramage, P.; Petrov, V.; Hamm, S.; Gelperina, S.; Engelhardt, B.; Alyautdin, R.; Briesen, H.; Begley, D. Pharm. Res. 2003, 20, 409-416.
109. Tsuzuki, T.; Hama, T.; Hibi, T.; Konishi, R.; Futaki, S.; Kitagawa, K. Biochem. Pharmacol. 1991, 41, R5-R8.
110. Wong, A.; Toth, I.; Curr. Med. Chem. 2001, 8, 1123-1136.
111. Andersen, G.; Chistrup, L.; Sjøgren, P. J. Pain Symp. Management, 2003, 25, 74-91.
112. Smith, M.T.; South, S.M. Pain Rev. 2001, 8, 171-191.
113. Drouillat, B.; Kellam, B.; Dekany, G.; Starr, M.S.; Toth, I. Bioorg. Med. Chem. Lett., 1997, 7, 2247-2250
114. Kellam, B.; Drouillat, B.; Dekany, G.; Starr, M.S.; Toth, I. Int. J. Pharm. 1998, 161, 55-64.
115. Wong, A.K.; Ross, B.P.; Chan, Y.N.; Artursson, P.; Lazorova, L.; Jones, A.; Toth, I.; Eur. J. Pharm. Sci. 2002, 16, 113-118.
116. Toth, I.; Malkinson, J.P.; Flinn, N.S.; Drouillat, B.; Horvath, A. J. Med. Chem. 1999, 42, 4010-4013.
117. Lis, H.; Sharon, N. Eur. J. Biochem. 1993, 3, 97-130.
118. Poduslo, J.F.; Curran, G.L. Molecular Brain Research 1994, 23, 157-162.
119. (a) O'Connors, S.E.; Imperiali, B. Chem. Biol. 1996, 3, 803-812.
120. (b) Dwek, R.A. Chem. Rev. 1996, 96, 683-720.
121. (c) Varki, A. Glycobiology 1993, 3, 97-130.
122. (d) Kobata, A. Eur. J. Biochem. 1992, 209, 483-501.
123. Burger, K.; Kluge, M.; Fehn, S.; Koksch, B.; Hennig, L.; Müller, G. Angew. Chem. Int. Ed. 1999, 38, 1414-1416.
124. Seitz, O. Chem. Biochem. 2000, 1, 214-246.
125. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537.
126. Torres, J.L.; Reig, F.; Valencia, G.; Rodrgiuez, R.; Garcia-Anton, J.M. Int. J. Pept. Prot. Res. 1988, 31, 474-480.
127. Rodriguez, R.E.; Rodriguez, F.D.; Sacristan, M.P.; Torres, J.L.; Valencia, G.; Garcia Anton, J.M. Neurosci. Lett. 1989, 101, 89-94.
128. Varga, L.; Horvat, S.; Lemieux, C.; Schiller, P.W. Int.J. Peptide Protein Res. 1987, 30, 371-378.
129. Horvat, J.; Horvat, S.; Lemieux, C.; Schiller, P.W. Int. J. Peptide Protein Res. 1988, 31, 499-507.
130. Horvat, S.; Horvat, J.; Varga-Defterdarvovic, L.; Pavelic, K.; Chung, N.N.; Schiller, P.W. Int. J. Peptide Protein Res. 1993, 41, 309-404.
131. Skuric, M.; Horvat, J.; Horvat, S.; Chung, N.N.; Schiller, P.W. Int J. Peptide Protein Res. 1994, 43, 402-409.
132. Horvat, S.; Varga, L.; Pfutzner, A.; Suhartono, H.; Rubsamen-Waigmann, H. Helv. Chim. Acta. 1991, 74, 951-955
133. Paulsen, H. Angew. Chem. In. Ed. Engl. 1982, 21, 155-173.
134. Garg, H.G.; Jeanloz, R.W. Adv. Carbohydr. Chem. Biochem. 1985, 43, 135-201.
135. Mitchell, S.A.; Pratt, M.R.; Hruby, V. J.; Polt, R. J. Org. Chem. 2001, 66, 2327-2342.
136. Polt, R.; Porreca, F.; Szabo, L.Z.; Bilsky, E.J.; Davis, P., Abbruscto, T.J.; Davis, T.P.; Horvath, R.; Yamamura, H.I.; Hruby, V.J. Proc. Natl. Acad. Sci. 1994, 91, 7114-8.
137. Zajac, J.M.; Gacel, G.; Petit, F.; Dodey, P.; Rossignol, P.; Rogues, B.P. Biochem. Biophys. Res. Commun. 1983, 111, 390-397.
138. Egleton, R.D.; Mitchell, S.A.; Huber, J.D.; Janders, J.; Stropova, D.; Polt, R.; Yamamura, H.I.; Hruby, V.J.; Davis, T.P. Brain Res. 2000, 881, 37-46.
139. Egleton, R.D.; Mitchell, S.A.; Huber, J.D.; Palian, M.M.; Polt, R.; Davis, T.P. J. Pharmacol. Exp. Ther. 2001, 299, 967-972.
140. Bilsky, E.J.; Egleton, R.D.; Mitchell, S.A.; Palian, M.M.; Davis, P. Huber, J.D.; Jones, H.; Yamamura, H.I.; Janders, J.; Davis, T.P.; Porreca, F.; Hruby, V.J.; Polt, R. J. Med. Chem. 2000, 43, 2586-2590.
141. Elmagbari, N.O.; Egleton, R.D.; Palian, M.M.; Lowery, J.J.; Schmid, W.R.; Davis, P.; Navratilova, E.; Dhanasekaran, M.; Keyari, C.M.; Yamamura, H.I.; Porreca, F.; Hruby, V.J.; Polt, R.; Bilsky, E.J. J. Pharm. Exp. Therap. 2004, in press.
142. Palian, M.M.; Boguslavsky, V.I.; O'Brien, D.F.; Polt, R. J. Am. Chem. Soc. 2003, 125, 5823-5831.
143. (a) Brantl, V.; Teschemacher, H.; Henschen, A.; Lottspeich, F. Hoppe-Seyler's Z. Physiol. Chem. 1979, 360, 1211.
144. (b) Zioudrou, C.; Streaty, R.A.; Klee, W.A. J. Biol. Chem., 1979, 254, 2446.
145. Elmagbari, N.O.; Egleton, R.D.; Palian, M.M.; Lowery, J.J.; Schmid, W.R.; Davis, P.; Navratilova, E.; Dhanasekaran, M.; Keyari, C.M.; Yamamura, H.I.; Porreca, F.; Hruby, V.J.; Polt, R.; Bilsky, E.J. J. Pharm. Exp. Therap. 2004, in press.
146. Bardaji, E.; Torres, J.L.; Clapes, P.; Aalbericio, F.; Barany, G.; Rodrigues, R.E.; Sacristan, M.P.; Valencia, G. J. Chem. Soc. Perkin Trans., 1991, 1, 1755-9.
147. Fiori, A.; Cardelli, P.; Negri, L.; Savi, M.R.; Storm, R. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 9469-9474.
148. Tomatis, R.; Marastoni, M.; Balboni, G.; Guerrini, R.; Capasso, A.; Sorrentino, L.; Santagada, V.; Caliendo, G.; Lazarus, L.H.; Salvadori, S. J. Med. Chem. 1997, 40, 2948-52.
149. Negri, L.; Lattanzi, R.; Tabacco, F.; Orru, L.; Severini, C.; Scolaro, B.; Rocchi, R. J. Med. Chem. 1999, 42, 400-404.
150. Juvadi, P.; Vunnam, S.; Merrifield, R.B. J. Am. Chem. Soc. 1996, 118, 8969-8997.
151. Schwyzer, R.; Gysen, B. Arch. Biochem. Biophys. 1983, 225, 467-474.
152. Schwyzer, R. Biochemistry 1986, 25, 6336-6342.
153. Fletcher, J.E.; Jiang, M.S. Toxicon, 1993, 31, 669-95.