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Volumn 57, Issue 13, 2014, Pages 5748-5763

New orally active dual enkephalinase inhibitors (DENKIs) for central and peripheral pain treatment

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 (1 ETHOXYCARBONYLMETHYLOXYCARBONYLETHYL) CARBAMOYL] 3 THIOPHEN 3 YLPROPYLDISULFANYLMETHYL] 3 METHYLSULFANYLPROPYL AMMONIUM TRIFLUOROACETATE; 1 [2 [1 (2 ETHOXYCARBONYLOXYETHOXYCARBONYL) ETHYLCARBAMOYL] 3 THIOPHEN 3 YLPROPYLDISULFONYLMETHYL] 3 METHYLSULFANYLPROPYL AMMONIUM TRIFLUOROACETATE; 1 [2 [1 (2 HYDROXY 1 HYDROXYMETHYLETHOXYCARBONYL) ETHYLCARBAMOYL] 3 THIOPHEN 3 YLPROPYLDISULFANYLMETHYL] 3 METHYLSULFANYL PROPYL AMMONIUM TRIFLUOROACETATE; 1 [2 [1 (2 METHANESULFONYLETHOXYCARBONYL) ETHYLCARBAMOYL] 3 THIOPHEN 3 YLPROPYLDISULFONYLMETHYL] 3 METHYLSULFANYLPROPYL AMMONIUM TRIFLUOROACETATE; 1 [2 [1 (2,3 DIACETOPROPOXYCARBONYL)ETHYLCARBAMOYL] 3 THIOPHEN 3 YKPROPYLDISULFANULMETHYL] 3 METHYLSULFANYLPROPYL AMONIUM TRIFLUOROACETATE; 3 METHYLSULFANYL 1 [2 [1 (3,4,5,6 TETRAHYDROXYTETRAHYDROPYRAN 2 YLMETHOXYCARBONYL] ETHYLCARBAMOYL] 3 THIOPHEN 3 YL PROPYLDISULFANYLMETHYL] PROPYO AMMONIUM TRIFLUOROACETATE; ANALGESIC AGENT; ENKEPHALIN; ENKEPHALINASE INHIBITOR; MEMBRANE METALLOENDOPEPTIDASE; MICROSOMAL AMINOPEPTIDASE; UNCLASSIFIED DRUG;

EID: 84904283325     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm500602h     Document Type: Article
Times cited : (49)

References (79)
  • 2
    • 0032910977 scopus 로고    scopus 로고
    • Are opioids effective in relieving neuropathic pain?
    • DOI 10.1016/S0304-3959(98)00256-5, PII S0304395998002565
    • Dellemijn, P. Are opioids effective in relieving neuropathic pain? Pain 1999, 80, 453-462 (Pubitemid 29182695)
    • (1999) Pain , vol.80 , Issue.3 , pp. 453-462
    • Dellemijn, P.1
  • 3
    • 0015918260 scopus 로고
    • Opiate receptor: Demonstration in nervous tissue
    • Pert, C. B.; Snyder, S. A. Opiate receptor: demonstration in nervous tissue Science 1973, 179, 1011-1014
    • (1973) Science , vol.179 , pp. 1011-1014
    • Pert, C.B.1    Snyder, S.A.2
  • 4
    • 0015836182 scopus 로고
    • Stereospecific binding of potent narcotic analgesic 3H-etorphine to rat brain homogenate
    • Simon, E. J.; Hiller, J. M.; Edelman, I. Stereospecific binding of potent narcotic analgesic 3H-etorphine to rat brain homogenate Proc. Natl. Acad. Sci. U. S. A. 1973, 70, 1947-1949
    • (1973) Proc. Natl. Acad. Sci. U. S. A. , vol.70 , pp. 1947-1949
    • Simon, E.J.1    Hiller, J.M.2    Edelman, I.3
  • 5
    • 0015763739 scopus 로고
    • Characteristics of the "receptor" for narcotic analgesics in synaptic plasmas membrane fraction from rat brain
    • Terenius, L. Characteristics of the "receptor" for narcotic analgesics in synaptic plasmas membrane fraction from rat brain Acta Pharmacol. Toxicol. 1973, 33, 372-384
    • (1973) Acta Pharmacol. Toxicol. , vol.33 , pp. 372-384
    • Terenius, L.1
  • 6
    • 0016701344 scopus 로고
    • Identification of the two related pentapeptides from the brain with potent opiate agonist activity
    • Hugues, J.; Smith, T. W.; Kosterlitz, H. W.; Fothergill, L. A.; Morgan, B. A.; Morris, H. R. Identification of the two related pentapeptides from the brain with potent opiate agonist activity Nature 1975, 258, 577-579
    • (1975) Nature , vol.258 , pp. 577-579
    • Hugues, J.1    Smith, T.W.2    Kosterlitz, H.W.3    Fothergill, L.A.4    Morgan, B.A.5    Morris, H.R.6
  • 9
    • 0017262602 scopus 로고
    • Analgesia induced in vivo by central administration of enkephalin in rat
    • Belluzzi, J. D.; Grant, N.; Garsky, V.; Sarantakis, D.; Wise, C. D.; Stein, L. Analgesia induced in vivo by central administration of enkephalin in rat Nature 1976, 260, 625-626
    • (1976) Nature , vol.260 , pp. 625-626
    • Belluzzi, J.D.1    Grant, N.2    Garsky, V.3    Sarantakis, D.4    Wise, C.D.5    Stein, L.6
  • 10
    • 36949034306 scopus 로고    scopus 로고
    • 5-enkephalin degradation kinetics by human brain preparations
    • DOI 10.1007/s11064-007-9418-6
    • Mosmaim, A. D.; Nguyen, T. D.; Tse, R.; Puente, J.; Couceyro, P.; Wolf, M. E. In vitro methionine5-enkephalin degradation kinetics by human brain preparations Neurochem. Res. 2008, 33, 81-86 (Pubitemid 350242794)
    • (2008) Neurochemical Research , vol.33 , Issue.1 , pp. 81-86
    • Mosnaim, A.D.1    Nguyen, T.D.2    Tse, R.3    Puente, J.4    Couceyro, P.5    Wolf, M.E.6
  • 11
    • 0017683782 scopus 로고
    • A synthetic enkephalin analogue with prolonged parenteral and oral analgesic activity
    • DOI 10.1038/268547a0
    • Römer, D.; Buscher, H. H.; Hill, R. C.; Pless, J.; Bauer, W.; Cardinaux, F.; Closse, A.; Hauser, D.; Huguenin, R. A. A synthetic enkephalin analogue with prolonged parenteral and oral analgesic activity Nature 1977, 268, 547-549 (Pubitemid 8153908)
    • (1977) Nature , vol.268 , Issue.5620 , pp. 547-549
    • Roemer, D.1    Buescher, H.H.2    Hill, R.C.3
  • 12
    • 0018578471 scopus 로고
    • Effects of the synthetic enkephalin analogue FK 33-824 on pain threshold and pain tolerance in man
    • DOI 10.1016/0304-3959(79)90007-1
    • Stacher, G.; Bauer, P.; Steinringer, H.; Schreiber, E.; Schmierer, G. Effects of the synthetic enkephalin analogue FK33-824 on pain threshold and pain tolerance in man Pain 1979, 7, 159-172 (Pubitemid 10198510)
    • (1979) Pain , vol.7 , Issue.2 , pp. 159-172
    • Stacher, G.1    Bauer, P.2    Steinringer, H.3
  • 14
    • 84859324853 scopus 로고    scopus 로고
    • Inhibiting the breakdown of endogenous opioids and cannabinoids to alleviate pain
    • Roques, B. R.; Fournie-Zaluski, M. C.; Wurm, M. Inhibiting the breakdown of endogenous opioids and cannabinoids to alleviate pain Nature Rev. Drug Discovery 2012, 11, 292-310
    • (2012) Nature Rev. Drug Discovery , vol.11 , pp. 292-310
    • Roques, B.R.1    Fournie-Zaluski, M.C.2    Wurm, M.3
  • 15
    • 0027475050 scopus 로고
    • Neutral endopeptidase 24.11: Structure, inhibition, and experimental and clinical pharmacology
    • Roques, B. P.; Noble, F.; Daugé, V.; Fournie-Zaluski, M. C.; Beaumont, A. Neutral endopeptidase 24.11: structure, inhibition, and experimental and clinical pharmacology Pharmacol. Rev. 1993, 45, 87-146 (Pubitemid 23108243)
    • (1993) Pharmacological Reviews , vol.45 , Issue.1 , pp. 87-146
    • Roques, B.P.1    Noble, F.2    Dauge, V.3    Fournie-Zaluski, M.-C.4    Beaumont, A.5
  • 16
    • 0019258298 scopus 로고
    • The enkephalinase inhibitor thiorphan shows antinociceptive activity in mice
    • DOI 10.1038/288286a0
    • Roques, B. P.; Fournié-Zaluski, M. C.; Soroca, E.; Lecomte, J. M.; Malfroy, B.; Llorens, C.; Schwartz, J. C. The enkephalinase inhibitor thiorphan shows antinociceptive activity in mice Nature 1980, 288, 286-288 (Pubitemid 11165881)
    • (1980) Nature , vol.288 , Issue.5788 , pp. 286-288
    • Roques, B.P.1    Fournie-Zaluski, M.C.2    Soroca, E.3
  • 17
    • 0017236348 scopus 로고
    • Bestatin, an inhibitor of aminopeptidase B, produced by actinomycetes
    • Umezawa, H.; Aoyagi, T.; Suda, H.; Hamada, M.; Takeuchi, T. Bestatin, an inhibitor of aminopeptidase B, produced by actinomycetes J. Antibiot. 1976, 29, 97-99
    • (1976) J. Antibiot. , vol.29 , pp. 97-99
    • Umezawa, H.1    Aoyagi, T.2    Suda, H.3    Hamada, M.4    Takeuchi, T.5
  • 18
    • 0022453270 scopus 로고
    • Effects of kelatorphan and other peptidase inhibitors on the in vitro and in vivo release of methionine-enkephalin-like material from the rat spinal cord
    • Bourgoin, S.; Le Bars, D.; Artaud, F.; Clot, A. M.; Bouboutou, R.; Fournie-Zaluski, M. C.; Roques, B. P.; Hamon, M.; Cesselin, F. Effects of kelatorphan and other peptidase inhibitors on the in vitro and in vivo release of methionine-enkephalin-like material from the rat spinal cord J. Pharmacol. Exp. Ther. 1986, 238, 360-366 (Pubitemid 16058339)
    • (1986) Journal of Pharmacology and Experimental Therapeutics , vol.238 , Issue.1 , pp. 360-366
    • Bourgoin, S.1    Le Bars, D.2    Artaud, F.3
  • 19
    • 0021268356 scopus 로고
    • Analgesic effects of kelatorphan, a new highly potent inhibitor of multiple enkephalin degrading enzymes
    • Fournie-Zaluski, M. C.; Chaillet, P.; Bouboutou, R.; Coulaud, A.; Cherot, P.; Waksman, G.; Costentin, J.; Roques, B. P. Analgesic effects of kelatorphan, a new highly potent inhibitor of multiple enkephalin degrading enzymes Eur. J. Pharmacol. 1984, 102, 525-528 (Pubitemid 14064094)
    • (1984) European Journal of Pharmacology , vol.102 , Issue.3-4 , pp. 525-528
    • Fournie-Zaluski, M.-C.1    Chaillet, P.2    Bouboutou, R.3
  • 20
    • 0026704581 scopus 로고
    • Inhibition of the enkephalin metabolizing enzymes by the first systemically active mixed inhibitor pro-drug RB101 induces potent analgesic responses in mice and rats
    • Noble, F.; Soleilhac, J. M.; Soroca-Lucas, E.; Turcaud, S.; Fournié-Zaluski, M. C.; Roques, B. P. Inhibition of the enkephalin metabolizing enzymes by the first systemically active mixed inhibitor pro-drug RB101 induces potent analgesic responses in mice and rats J. Pharm. Exp. Ther. 1992, 261, 181-190
    • (1992) J. Pharm. Exp. Ther. , vol.261 , pp. 181-190
    • Noble, F.1    Soleilhac, J.M.2    Soroca-Lucas, E.3    Turcaud, S.4    Fournié-Zaluski, M.C.5    Roques, B.P.6
  • 21
    • 0022900635 scopus 로고
    • The enkephalinase inhibitor, GB 52, does not affect nociceptive flexion reflexes nor pain sensation in humans
    • DOI 10.1016/0028-3908(86)90004-3
    • Willer, J. C.; Roby, A.; Ernst, M. The enkephalinase inhibitor, GB 52, does not affect nociceptive flexion reflexes nor pain sensation in humans Neuropharmacology 1986, 25, 819-822 (Pubitemid 16045943)
    • (1986) Neuropharmacology , vol.25 , Issue.8 , pp. 819-822
    • Willer, J.C.1    Roby, A.2    Ernst, M.3
  • 22
    • 0024152385 scopus 로고
    • Potent analgesic effects of inhibitors of enkephalin metabolism administered intrathecally to cancer patients
    • Meynadier, J.; Dalmas, S.; Lecomte, J. M.; Gros, C. I.; Schwartz, J. C. Potent analgesic effects of inhibitors of enkephalin metabolism administered intrathecally to cancer patients Pain Clinic 1988, 2, 201-205 (Pubitemid 19202772)
    • (1988) Pain Clinic , vol.2 , Issue.4 , pp. 201-205
    • Meynadier, J.1    Dalmas, S.2    Lecomte, J.M.3    Gros, Ci.4    Schwartz Ch., J.5
  • 24
    • 0037824374 scopus 로고    scopus 로고
    • 2 antagonist or methadone
    • DOI 10.1016/S0304-3959(02)00486-4
    • Le Guen, S.; Mas Nieto, M.; Canestrelli, C.; Chen, H.; Fournie-Zaluski, M. C.; Cupo, A.; Maldonado, R.; Roques, B. P.; Noble, F. Pain management by a new series of dual inhibitors of enkephalin degrading enzymes: long lasting antinociceptive properties and potentiation by CCK2 antagonist or methadone Pain 2003, 104, 139-148 (Pubitemid 36835882)
    • (2003) Pain , vol.104 , Issue.1-2 , pp. 139-148
    • Le Guen, S.1    Mas Nieto, M.2    Canestrelli, C.3    Chen, H.4    Fournie-Zaluski, M.-C.5    Cupo, A.6    Maldonado, R.7    Roques, B.P.8    Noble, F.9
  • 25
    • 0029799253 scopus 로고    scopus 로고
    • The dual peptidase inhibitor RB101 induces a long-lasting increase in the extracellular level of Met-enkephalin-like material in the nucleus accumbens of freely moving rats
    • Dauge, V.; Mauborgne, A.; Cesselin, F.; Fournie-Zaluski, M. C.; Roques, B. P. The dual peptidase inhibitor RB101 induces a long-lasting increase in the extracellular level of Met-enkephalin-like material in the nucleus accumbens of freely moving rats J. Neurochem. 1996, 67, 1301-1308 (Pubitemid 26277945)
    • (1996) Journal of Neurochemistry , vol.67 , Issue.3 , pp. 1301-1308
    • Dauge, V.1    Mauborgne, A.2    Cesselin, F.3    Fournie-Zaluski, M.-C.4    Roques, B.-P.5
  • 27
    • 0026659612 scopus 로고
    • Mixed inhibitor-pro-drug" as a new approach toward systemically active inhibitors of enkephalin-degrading enzyme
    • Fournie-Zaluski, M. C.; Coric, P.; Turcaud, S.; Lucas, E.; Noble, F.; Maldonado, R.; Roques, B. P. Mixed inhibitor-pro-drug" as a new approach toward systemically active inhibitors of enkephalin-degrading enzyme J. Med. Chem. 1992, 35, 2473-2481
    • (1992) J. Med. Chem. , vol.35 , pp. 2473-2481
    • Fournie-Zaluski, M.C.1    Coric, P.2    Turcaud, S.3    Lucas, E.4    Noble, F.5    Maldonado, R.6    Roques, B.P.7
  • 28
    • 0031465021 scopus 로고    scopus 로고
    • Pain-suppressive effects on various nociceptive stimuli (thermal, chemical, electrical and inflammatory) of the first orally active enkephalin-metabolizing enzyme inhibitor RB 120
    • DOI 10.1016/S0304-3959(97)00125-5, PII S0304395997001255
    • Noble, F.; Smadja, C.; Valverde, O.; Maldonado, R.; Coric, P.; Turcaud, S.; Fournié-Zaluski, M. C.; Roques, B. P. Pain-suppressive effects on various nociceptive stimuli (thermal, chemical, electrical and inflammatory) of the first orally active enkephalin-metabolizing enzyme inhibitor RB120 Pain 1997, 73, 383-391 (Pubitemid 28021843)
    • (1997) Pain , vol.73 , Issue.3 , pp. 383-391
    • Noble, F.1    Smadja, C.2    Valverde, O.3    Maldonado, R.4    Coric, P.5    Turcaud, S.6    Fournie-Zaluski, M.-C.7    Roques, B.P.8
  • 29
    • 0032578513 scopus 로고    scopus 로고
    • Aminophosphinic inhibitors as transition state analogues of enkephalin-degrading enzymes: A class of central analgesics
    • Chen, H.; Noble, F.; Coric, P.; Fournie-Zaluski, M. C.; Roques, B. P. Aminophosphinic inhibitors as transition state analogues of enkephalin-degrading enzymes: a class of central analgesics Proc. Natl. Acad. Sci. U. S. A. 1998, 95, 12028-12033
    • (1998) Proc. Natl. Acad. Sci. U. S. A. , vol.95 , pp. 12028-12033
    • Chen, H.1    Noble, F.2    Coric, P.3    Fournie-Zaluski, M.C.4    Roques, B.P.5
  • 30
    • 0028926637 scopus 로고
    • Assessment of endogenous enkephalins efficacy in the hot plate test in mice: Comparative study with morphine
    • Noble, F.; Roques, B. P. Assessment of endogenous enkephalins efficacy in the hot plate test in mice: comparative study with morphine Neurosci. Lett. 1995, 185, 75-78
    • (1995) Neurosci. Lett. , vol.185 , pp. 75-78
    • Noble, F.1    Roques, B.P.2
  • 31
    • 1842663254 scopus 로고    scopus 로고
    • Local peripheral effects of μ-opioid receptor agonists in neuropathic pain in rats
    • DOI 10.1016/j.neulet.2004.01.056, PII S0304394004001338
    • Obara, I.; Przewlocki, R.; Przewlocka, B. Local peripheral effects of mu-opioid receptor agonists in neuropathic pain in rats Neurosci. Lett. 2004, 360, 85-89 (Pubitemid 38471994)
    • (2004) Neuroscience Letters , vol.360 , Issue.1-2 , pp. 85-89
    • Obara, I.1    Przewlocki, R.2    Przewlocka, B.3
  • 32
  • 33
    • 0041965945 scopus 로고    scopus 로고
    • Attacking pain at its source: New perspectives on opioids
    • DOI 10.1038/nm908
    • Stein, C.; Schafer, M.; Machelska, H. Attacking pain at its source: new perspectives on opioids Nature Med. 2003, 9, 1003-1008 (Pubitemid 37021779)
    • (2003) Nature Medicine , vol.9 , Issue.8 , pp. 1003-1008
    • Stein, C.1    Schafer, M.2    Machelska, H.3
  • 34
    • 0036154064 scopus 로고    scopus 로고
    • Roles of endogenous opioid peptides in modulation of nocifensive response to formalin
    • Wu, H. E.; Hung, K. C.; Mizoguchi, H.; Nagase, H.; Tseng, L. F. Roles of endogenous opioid peptides in modulation of nocifensive response to formalin J. Pharmacol. Exp. Ther. 2002, 300, 647-654
    • (2002) J. Pharmacol. Exp. Ther. , vol.300 , pp. 647-654
    • Wu, H.E.1    Hung, K.C.2    Mizoguchi, H.3    Nagase, H.4    Tseng, L.F.5
  • 37
    • 0027175997 scopus 로고
    • Gem-cycloalkyl substituted thiol inhibitors of neutral endopeptidase 24.11. Synthesis via nucleophilic opening of 2,2-spiro-β-lactones
    • DOI 10.1016/S0960-894X(00)80674-5
    • James, K.; Palmer, M. J. gem -Cycloalkyl substituted thiol inhibitors of neutral endopeptidase 24.11. Synthesis via nucleophilic opening of 2,2-spiro-β-lactones Bioorg. Med. Chem. Lett. 1993, 3, 825-830 (Pubitemid 23149566)
    • (1993) Bioorganic and Medicinal Chemistry Letters , vol.3 , Issue.5 , pp. 825-830
    • James, K.1    Palmer, M.J.2
  • 38
    • 0028299371 scopus 로고
    • New dual inhibitors of neutral endopeptidase and angiotensin-converting enzyme: Rational design, bioavailability, and pharmacological responses in experimental hypertension
    • Fournie-Zaluski, M. C.; Coric, P.; Turcaud, S.; Rousselet, N.; Gonzalez, W.; Barbe, B.; Pham, I.; Jullian, N.; Michel, J. B.; Roques, B. P. New dual inhibitors of neutral endopeptidase and angiotensin-converting enzyme: rational design, bioavailability, and pharmacological responses in experimental hypertension J. Med. Chem. 1994, 37, 1070-1083 (Pubitemid 24145368)
    • (1994) Journal of Medicinal Chemistry , vol.37 , Issue.8 , pp. 1070-1083
    • Fournie-Zaluski, M.-C.1    Coric, P.2    Turcaud, S.3    Rousselet, N.4    Gonzalez, W.5    Barbe, B.6    Pham, I.7    Jullian, N.8    Michel, J.-B.9    Roques, B.P.10
  • 40
    • 0027963431 scopus 로고
    • Mercaptoacyl amino acid inhibitors of atriopeptidase. 1. Structure- activity relationship studies of methionine and S-alkylcysteine derivatives
    • DOI 10.1021/jm00041a026
    • Neustadt, B. R.; Smith, E. S.; Nechuta, T. L.; Bronnenkant, A. A.; Haslanger, M. F.; Watkins, R. W.; Foster, C. J.; Sybertz, E. J. Mercaptoacyl aminoacid inhibitors of atriopeptidase. 1. Structure-activity relationship studies of methionine and S -alkylcysteine derivatives J. Med. Chem. 1994, 37, 2461-2476 (Pubitemid 24262336)
    • (1994) Journal of Medicinal Chemistry , vol.37 , Issue.15 , pp. 2461-2476
    • Neustadt, B.R.1    Smith, E.M.2    Nechuta, T.L.3    Bronnenkant, A.A.4    Haslanger, M.F.5    Watkins, R.W.6    Foster, C.J.7    Sybertz, E.J.8
  • 41
    • 0030656549 scopus 로고    scopus 로고
    • A ring opening reaction of benzisothiazolones. A new route to unsymmetrical disulfides
    • Sanchez, J. P. A ring opening reaction of benzisothiazolones. A new route to unsymmetrical disulfides J. Heterocycl. Chem. 1997, 34, 1463-1467 (Pubitemid 27516119)
    • (1997) Journal of Heterocyclic Chemistry , vol.34 , Issue.5 , pp. 1463-1467
    • Sanchez, J.P.1
  • 43
    • 0027769421 scopus 로고
    • Synthesis and inhibitory activity of optically active 2-benzyl-3- mercaptopropanoic acid against carboxypeptidase A
    • DOI 10.1016/S0960-894X(01)80741-1
    • Kim, D. H.; Kim, Y. J. Synthesis and inhibitory activity of optically active 2-benzyl-3-mercaptopropanoic acid against carboxypeptidase A Bioorg. Med. Chem. Lett. 1993, 3, 2681-2684 (Pubitemid 24040996)
    • (1993) Bioorganic and Medicinal Chemistry Letters , vol.3 , Issue.12 , pp. 2681-2684
    • Kim, D.H.1    Yeon Ju Kim2
  • 44
    • 85004776917 scopus 로고
    • Alkyl 1-chloroalkylcarbonates: Reagents for the synthesis of carbamates and protection of amino groups
    • Barcelo, G.; Senet, J. P.; Sennyey, G.; Bensoam, J.; Loffet, A. Alkyl 1-chloroalkylcarbonates: reagents for the synthesis of carbamates and protection of amino groups Synthesis 1986, 8, 627-632
    • (1986) Synthesis , vol.8 , pp. 627-632
    • Barcelo, G.1    Senet, J.P.2    Sennyey, G.3    Bensoam, J.4    Loffet, A.5
  • 45
    • 0014211618 scopus 로고
    • On the size of the active site in proteases. I. Papain
    • Schechter, I.; Burger, A. On the size of the active site in proteases. I. Papain Biochem. Biophys. Res. Commun. 1967, 27, 157-162
    • (1967) Biochem. Biophys. Res. Commun. , vol.27 , pp. 157-162
    • Schechter, I.1    Burger, A.2
  • 47
    • 0034681296 scopus 로고    scopus 로고
    • Structure of human neutral endopeptidase (neprilysin) complexed with Phosphoramidon
    • Oefner, C.; D'Arcy, A.; Hennig, M.; Winkler, F. K.; Dale, G. Structure of human neutral endopeptidase (neprilysin) complexed with Phosphoramidon Mol. Biol. 2000, 296, 341-349
    • (2000) Mol. Biol. , vol.296 , pp. 341-349
    • Oefner, C.1    D'Arcy, A.2    Hennig, M.3    Winkler, F.K.4    Dale, G.5
  • 48
    • 45249125997 scopus 로고
    • Thiophenes as phenyl bio-isosteres: Application in radiopharmaceutical design. I. Dopamine uptake antagonists
    • DOI 10.1016/0883-2897(89)90138-4
    • Kilbourn, M. R. Thiophenes as phenyl bio-isosteres: application in radiopharmaceutical design-I. Dopamine uptake antagonists Nucl. Med. Biol. 1989, 16, 681-686 (Pubitemid 19269401)
    • (1989) Nuclear Medicine and Biology , vol.16 , Issue.7 , pp. 681-686
    • Kilbourn, M.R.1
  • 49
    • 1542313980 scopus 로고    scopus 로고
    • Methionine Sulfoxide Reduction in Mammals: Characterization of Methionine-R-Sulfoxide Reductases
    • DOI 10.1091/mbc.E03-08-0629
    • Kim, H. Y.; Gladyshev, V. N. Methionine sulfoxyde reduction in mammals: characterization of methionine- R -sulfoxyde reductase Mol. Biol. Cell 2004, 15, 1055-1064 (Pubitemid 38316216)
    • (2004) Molecular Biology of the Cell , vol.15 , Issue.3 , pp. 1055-1064
    • Kim, H.-Y.1    Gladyshev, V.N.2
  • 50
    • 84935383230 scopus 로고
    • Synthetic analgesics: Dithienylbutenyl and dithienylbutylamines
    • Eddy, N. B.; Leimbach, D. Synthetic analgesics: dithienylbutenyl and dithienylbutylamines J. Pharm. Exp. Ther. 1953, 107, 385-389
    • (1953) J. Pharm. Exp. Ther. , vol.107 , pp. 385-389
    • Eddy, N.B.1    Leimbach, D.2
  • 52
    • 84855622126 scopus 로고    scopus 로고
    • Virtual Computational Chemistry Laboratory.
    • ALOGPs 2.1 Program; Virtual Computational Chemistry Laboratory, 2005; http://www.vcclab.org/lab/alogps/.
    • (2005) ALOGPs 2.1 Program
  • 53
    • 0002261078 scopus 로고
    • A method for determining loss of pain sensation
    • D'Amour, F. E.; Smith, D. L. A method for determining loss of pain sensation J. Pharm. Exp. Ther. 1941, 72, 74-79
    • (1941) J. Pharm. Exp. Ther. , vol.72 , pp. 74-79
    • D'Amour, F.E.1    Smith, D.L.2
  • 54
    • 0021846807 scopus 로고
    • Formalin test in mice, a useful technique for evaluating mild analgesics
    • DOI 10.1016/0165-0270(85)90116-5
    • Hunskaar, S.; Fasmer, O. B.; Hole, K. Formalin test in mice, a useful technique for evaluating mild analgesics J. Neurosci. Methods 1985, 14, 69-76 (Pubitemid 15037763)
    • (1985) Journal of Neuroscience Methods , vol.14 , Issue.1 , pp. 69-76
    • Hunskaar, S.1    Fasmer, O.B.2    Hole, K.3
  • 56
    • 0023924046 scopus 로고
    • A new and sensitive method for measuring thermal nociception in cutaneous hyperalgesia
    • Hargreaves, K.; Dubner, R.; Brown, F.; Flores, C.; Joris, J. A new and sensitive method for measuring thermal nociception in cutaneous hyperalgesia Pain 1988, 32, 77-88
    • (1988) Pain , vol.32 , pp. 77-88
    • Hargreaves, K.1    Dubner, R.2    Brown, F.3    Flores, C.4    Joris, J.5
  • 57
    • 0023895875 scopus 로고
    • A peripheral mononeuropathy in rat that produces disorders of pain sensation like those seen in man
    • Bennett, G. J.; Xie, Y. K. A peripheral mononeuropathy in rat that produces disorders of pain sensation like those seen in man Pain 1988, 33, 87-107
    • (1988) Pain , vol.33 , pp. 87-107
    • Bennett, G.J.1    Xie, Y.K.2
  • 58
    • 0025167399 scopus 로고
    • A novel behavioral model of neuropathic pain disorders produced in rats by partial sciatic nerve injury
    • DOI 10.1016/0304-3959(90)91074-S
    • Seltzer, Z.; Dubner, R.; Shir, Y. A novel behavorial model of neuropathic pain disorders produced in rats by partial sciatic nerve injury Pain 1990, 43, 205-218 (Pubitemid 20385185)
    • (1990) Pain , vol.43 , Issue.2 , pp. 205-218
    • Seltzer, Z.1    Dubner, R.2    Shir, Y.3
  • 59
    • 65849395509 scopus 로고    scopus 로고
    • Enkephalinase inhibitors: Potential agents for the management of pain
    • Thanawala, V.; Kadam, V. J.; Ghosh, R. Enkephalinase inhibitors: potential agents for the management of pain Curr. Drug Targets 2008, 9, 887-894
    • (2008) Curr. Drug Targets , vol.9 , pp. 887-894
    • Thanawala, V.1    Kadam, V.J.2    Ghosh, R.3
  • 60
    • 0025731698 scopus 로고
    • Effects of [ n -(l-(1-carboxy-2-phenyl)ethyl]-l-phenylalanyl-beta-alanine (SCH32615), a neutral endopeptidase (enkephalinase) inhibitor, on levels of enkephalin, encrypted enkephalins and substance P in cerebrospinal fluid and plasma of primates
    • Yaksh, T. L.; Sabbe, M. B.; Lucas, D.; Mjanger, E.; Chipkin, R. E. Effects of [ n -(l-(1-carboxy-2-phenyl)ethyl]-l-phenylalanyl-beta-alanine (SCH32615), a neutral endopeptidase (enkephalinase) inhibitor, on levels of enkephalin, encrypted enkephalins and substance P in cerebrospinal fluid and plasma of primates J. Pharmacol. Exp. Ther. 1991, 256, 1033-41
    • (1991) J. Pharmacol. Exp. Ther. , vol.256 , pp. 1033-1041
    • Yaksh, T.L.1    Sabbe, M.B.2    Lucas, D.3    Mjanger, E.4    Chipkin, R.E.5
  • 64
    • 33947295869 scopus 로고
    • An efficient synthesis of symmetrical 1,3-diglycerides
    • Bentley, P. H.; McCrae, W. An efficient synthesis of symmetrical 1,3-diglycerides J. Org. Chem. 1970, 35, 2082-2083
    • (1970) J. Org. Chem. , vol.35 , pp. 2082-2083
    • Bentley, P.H.1    McCrae, W.2
  • 65
    • 12344273726 scopus 로고    scopus 로고
    • The blood-brain barrier: Bottleneck in brain drug development
    • DOI 10.1602/neurorx.2.1.3
    • Pardridge, W. M. The blood-brain barrier: bottleneck in brain drug development NeuroRx 2005, 2, 3-14 (Pubitemid 40128022)
    • (2005) NeuroRx , vol.2 , Issue.1 , pp. 3-14
    • Pardridge, W.M.1
  • 66
    • 84885338409 scopus 로고    scopus 로고
    • Targeting pain and inflammation by peripherally acting opioids
    • Stein, C. Targeting pain and inflammation by peripherally acting opioids Front. Pharmacol. 2013, 4, 1-3
    • (2013) Front. Pharmacol. , vol.4 , pp. 1-3
    • Stein, C.1
  • 67
    • 0023223448 scopus 로고
    • The formalin test in mice: Dissociation between inflammatory and non-inflammatory pain
    • DOI 10.1016/0304-3959(87)90088-1
    • Hunskaar, S.; Hole, K. The formalin test in mice: dissociation between inflammatory and non-inflammatory pain Pain 1987, 30, 103-114 (Pubitemid 17094194)
    • (1987) Pain , vol.30 , Issue.1 , pp. 103-114
    • Hunskaar, S.1    Hole, K.2
  • 68
    • 0031775956 scopus 로고    scopus 로고
    • Partial sciatic nerve injury in the mouse as a model of neuropathic pain: Behavioral and neuroanatomical correlates
    • DOI 10.1016/S0304-3959(98)00045-1, PII S0304395998000451
    • Malmberg, A. B.; Basbaum, A. I. Partial sciatic nerve injury in the mouse as a model of neuropathic pain: behavioral and neuroanatomical correlates Pain 1998, 76, 215-222 (Pubitemid 28304959)
    • (1998) Pain , vol.76 , Issue.1-2 , pp. 215-222
    • Malmberg, A.B.1    Basbaum, A.I.2
  • 69
    • 0036603005 scopus 로고    scopus 로고
    • Chronic pain and medullary descending facilitation
    • DOI 10.1016/S0166-2236(02)02157-4, PII S0166223602021574
    • Porreca, F.; Ossipov, M. H.; Gebhart, F. G. Chronic pain and medullary descending facilitation Trends Neurosci. 2002, 25, 319-325 (Pubitemid 34667014)
    • (2002) Trends in Neurosciences , vol.25 , Issue.6 , pp. 319-325
    • Porreca, F.1    Ossipov, M.H.2    Gebhart, G.F.3
  • 71
    • 0026010636 scopus 로고
    • Behavioural evidence that systemic morphine may modulate a phasic pain-related behavior in a rat model of peripheral mononeuropathy
    • Attal, N.; Chen, Y. L.; Kayser, V.; Guilbaud, G. Behavioural evidence that systemic morphine may modulate a phasic pain-related behavior in a rat model of peripheral mononeuropathy Pain 1991, 47, 65-70
    • (1991) Pain , vol.47 , pp. 65-70
    • Attal, N.1    Chen, Y.L.2    Kayser, V.3    Guilbaud, G.4
  • 72
    • 0027272042 scopus 로고
    • Selective opioid receptor agonists modulate mechanical allodynia in an animal model of neuropathic pain
    • DOI 10.1016/0304-3959(93)90224-D
    • Desmeules, J. A.; Kayser, V.; Guilbaud, G. Selective opioid receptor agonists modulate mechanical allodynia in an animal model of neuropathic pain Pain 1993, 53, 277-285 (Pubitemid 23172376)
    • (1993) Pain , vol.53 , Issue.3 , pp. 277-285
    • Desmeules, J.A.1    Kayser, V.2    Guilbaud, G.3
  • 73
    • 0032508735 scopus 로고    scopus 로고
    • Anti-allodynic actions of intravenous opioids in the nerve injured rat: Potential utility of heroin and dihydroetorphine against neuropathic pain
    • DOI 10.1016/S0014-2999(98)00531-7, PII S0014299998005317
    • Martin, T. J.; Hairston, C. T.; Lutz, P. O.; Harris, L. S.; Porreca, F. Anti-allodynic actions of intravenous opioids in the nerve injured rat: potential utility of heroin and dihydroetorphine against neuropathic pain Eur. J. Pharmacol. 1998, 357, 25-32 (Pubitemid 28439174)
    • (1998) European Journal of Pharmacology , vol.357 , Issue.1 , pp. 25-32
    • Martin, T.J.1    Hairston, C.T.2    Lutz, P.O.3    Harris, L.S.4    Porreca, F.5
  • 74
    • 0020050607 scopus 로고
    • Quaternary narcotic antagonists' relative ability to prevent antinociception and gastrointestinal transit inhibition in morphine-treated rats as an index of peripheral selectivity
    • DOI 10.1016/0024-3205(82)90467-2
    • Bianchi, G.; Fiocchi, R.; Tavani, A.; Manara, L. Quaternary narcotic antagonist relative ability to prevent antinociception and gastrointestinal transit inhibition in morphine-treated rats as an index of peripheral selectivity Life Sci. 1982, 30, 1875-1883 (Pubitemid 12098880)
    • (1982) Life Sciences , vol.30 , Issue.22 , pp. 1875-1883
    • Bianchi, G.1    Fiocchi, R.2    Tavani, A.3    Manara, L.4
  • 75
    • 0028355903 scopus 로고
    • Antinociceptive response induced by mixed inhibitors of enkephalin catabolism in peripheral inflammation
    • DOI 10.1016/0304-3959(94)90186-4
    • Maldonado, R.; Valverde, O.; Turcaud, S.; Fournie-Zaluski, M.-C.; Roques, B. P. Antinociceptive response induced by mixed inhibitors of enkephalin catabolism in peripheral inflammation Pain 1994, 58, 77-83 (Pubitemid 24221820)
    • (1994) Pain , vol.58 , Issue.1 , pp. 77-83
    • Maldonado, R.1    Valverde, O.2    Turcaud, S.3    Fournie-Zaluski, M.C.4    Roques, B.P.5
  • 76
    • 53049105222 scopus 로고    scopus 로고
    • Inhibition of osteosarcoma-induced thermal hyperalgesia in mice by the orally active dual enkephalinase inhibitor PL37. Potentialisation by gabapentin
    • Menendez, L.; Hidalgo, A.; Meana, A.; Poras, H.; Fournie-Zaluski, M.-C.; Roques, B. P. Inhibition of osteosarcoma-induced thermal hyperalgesia in mice by the orally active dual enkephalinase inhibitor PL37. Potentialisation by gabapentin Eur. J. Pharmacol. 2008, 596, 50-55
    • (2008) Eur. J. Pharmacol. , vol.596 , pp. 50-55
    • Menendez, L.1    Hidalgo, A.2    Meana, A.3    Poras, H.4    Fournie-Zaluski, M.-C.5    Roques, B.P.6
  • 77
  • 78
    • 0022978686 scopus 로고
    • Enkephalinase and angiotensin converting enzyme activities in human venous and arterial plasma
    • DOI 10.1016/0143-4179(86)90037-5
    • Spillantini, M. G.; Panconesi, A.; Del Bianco, P. L.; Sicuteri, F. Enkephalinase and angiotensin converting enzyme activities in human venous and arterial plasma Neuropeptides 1986, 8, 111-117 (Pubitemid 17185704)
    • (1986) Neuropeptides , vol.8 , Issue.2 , pp. 111-117
    • Spillantini, M.G.1    Panconesi, A.2    Del Bianco, P.L.3    Sicuteri, F.4


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