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Volumn 56, Issue 12, 2013, Pages 4953-4965

Constrained H-Phe-Phe-NH2 analogues with high affinity to the substance P 1-7 binding site and with improved metabolic stability and cell permeability

Author keywords

[No Author keywords available]

Indexed keywords

DEXTROMETHORPHAN; MIDAZOLAM; PEPTIDE TRANSPORTER 1; PYRROLIDINE DERIVATIVE; SUBSTANCE P [1-7]; SUBSTANCE P DERIVATIVE;

EID: 84879571004     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400209h     Document Type: Article
Times cited : (19)

References (52)
  • 1
    • 84944496221 scopus 로고
    • An unidentified depressor substance in certain tissue extracts
    • Von Euler, U. S.; Gaddum, J. H. An unidentified depressor substance in certain tissue extracts J. Physiol. 1931, 72, 74-87
    • (1931) J. Physiol. , vol.72 , pp. 74-87
    • Von Euler, U.S.1    Gaddum, J.H.2
  • 2
    • 0026100201 scopus 로고
    • Mammalian tachykinin receptors
    • Nakanishi, S. Mammalian tachykinin receptors Annu. Rev. Neurosci. 1991, 14, 123-136
    • (1991) Annu. Rev. Neurosci. , vol.14 , pp. 123-136
    • Nakanishi, S.1
  • 3
    • 0035137002 scopus 로고    scopus 로고
    • Substance P: A pioneer amongst neuropeptides
    • Hökfelt, T.; Pernow, B.; Wahren, J. Substance P: a pioneer amongst neuropeptides J. Intern. Med. 2001, 249, 27-40
    • (2001) J. Intern. Med. , vol.249 , pp. 27-40
    • Hökfelt, T.1    Pernow, B.2    Wahren, J.3
  • 4
    • 0019797854 scopus 로고
    • Purification and characterization of a membrane-bound substance P-degrading enzyme from human brain
    • Lee, C.-M.; Sandberg, B. E. B.; Hanley, M. R.; Iversen, L. L. Purification and characterization of a membrane-bound substance P-degrading enzyme from human brain Eur. J. Biochem. 1981, 114, 315-327
    • (1981) Eur. J. Biochem. , vol.114 , pp. 315-327
    • Lee, C.-M.1    Sandberg, B.E.B.2    Hanley, M.R.3    Iversen, L.L.4
  • 6
    • 0037302811 scopus 로고    scopus 로고
    • Neuropeptide conversion to bioactive fragments - An important pathway in neuromodulation
    • Hallberg, M.; Nyberg, F. Neuropeptide conversion to bioactive fragments-an important pathway in neuromodulation Curr. Protein Pept. Sci. 2003, 4, 31-44
    • (2003) Curr. Protein Pept. Sci. , vol.4 , pp. 31-44
    • Hallberg, M.1    Nyberg, F.2
  • 7
    • 0027175581 scopus 로고
    • Substance P-(1-7), a substance P metabolite, inhibits withdrawal jumping in morphine-dependent mice
    • Kreeger, J. S.; Larson, A. A. Substance P-(1-7), a substance P metabolite, inhibits withdrawal jumping in morphine-dependent mice Eur. J. Pharmacol. 1993, 238, 111-115
    • (1993) Eur. J. Pharmacol. , vol.238 , pp. 111-115
    • Kreeger, J.S.1    Larson, A.A.2
  • 9
    • 0037255632 scopus 로고    scopus 로고
    • Substance P(1-7) affects the expression of dopamine D2 receptor mRNA in male rat brain during morphine withdrawal
    • Zhou, Q.; Frändberg, P.-A.; Kindlundh, A. M. S.; Le Greves, P.; Nyberg, F. Substance P(1-7) affects the expression of dopamine D2 receptor mRNA in male rat brain during morphine withdrawal Peptides 2003, 24, 147-153
    • (2003) Peptides , vol.24 , pp. 147-153
    • Zhou, Q.1    Frändberg, P.-A.2    Kindlundh, A.M.S.3    Le Greves, P.4    Nyberg, F.5
  • 10
    • 33646763494 scopus 로고    scopus 로고
    • Modulation of peripheral inflammation by the substance P N-terminal metabolite substance P1-7
    • Wiktelius, D.; Khalil, Z.; Nyberg, F. Modulation of peripheral inflammation by the substance P N-terminal metabolite substance P1-7 Peptides 2006, 27, 1490-1497
    • (2006) Peptides , vol.27 , pp. 1490-1497
    • Wiktelius, D.1    Khalil, Z.2    Nyberg, F.3
  • 11
    • 2442597297 scopus 로고    scopus 로고
    • Occurrence of substance P(1-7) in the metabolism of substance P and its antinociceptive activity at the mouse spinal cord level
    • Sakurada, C.; Watanabe, C.; Sakurada, T. Occurrence of substance P(1-7) in the metabolism of substance P and its antinociceptive activity at the mouse spinal cord level Methods Find. Exp. Clin. Pharmacol. 2004, 26, 171-176
    • (2004) Methods Find. Exp. Clin. Pharmacol. , vol.26 , pp. 171-176
    • Sakurada, C.1    Watanabe, C.2    Sakurada, T.3
  • 12
    • 70649105396 scopus 로고    scopus 로고
    • Substance P1-7 induces antihyperalgesia in diabetic mice through a mechanism involving the naloxone-sensitive sigma receptors
    • Carlsson, A.; Ohsawa, M.; Hallberg, M.; Nyberg, F.; Kamei, J. Substance P1-7 induces antihyperalgesia in diabetic mice through a mechanism involving the naloxone-sensitive sigma receptors Eur. J. Pharmacol. 2010, 626, 250-255
    • (2010) Eur. J. Pharmacol. , vol.626 , pp. 250-255
    • Carlsson, A.1    Ohsawa, M.2    Hallberg, M.3    Nyberg, F.4    Kamei, J.5
  • 13
    • 0034079572 scopus 로고    scopus 로고
    • Patterns of quantitative sensation testing of hypoesthesia and hyperalgesia are predictive of diabetic polyneuropathy. A study of three cohorts
    • Dyck, P. J.; Dyck, P. J. B.; Velosa, J. A.; Larson, T. S.; O'Brien, P. C.; Grp, N. G. F. S. Patterns of quantitative sensation testing of hypoesthesia and hyperalgesia are predictive of diabetic polyneuropathy. A study of three cohorts Diabetes Care 2000, 23, 510-517
    • (2000) Diabetes Care , vol.23 , pp. 510-517
    • Dyck, P.J.1    Dyck, P.J.B.2    Velosa, J.A.3    Larson, T.S.4    O'Brien, P.C.5    Grp, N.G.F.S.6
  • 14
    • 0025412012 scopus 로고
    • Differential-effects of C-terminal and N-terminal substance-P metabolites on the release of amino-acid neurotransmitters from the spinal-cord. Potential role in nociception
    • Skilling, S. R.; Smullin, D. H.; Larson, A. A. Differential-effects of C-terminal and N-terminal substance-P metabolites on the release of amino-acid neurotransmitters from the spinal-cord. Potential role in nociception J. Neurosci. 1990, 10, 1309-1318
    • (1990) J. Neurosci. , vol.10 , pp. 1309-1318
    • Skilling, S.R.1    Smullin, D.H.2    Larson, A.A.3
  • 15
    • 0026763798 scopus 로고
    • Identification of a novel receptor mediating substance-P-induced behavior in the mouse
    • Mousseau, D. D.; Sun, X. F.; Larson, A. A. Identification of a novel receptor mediating substance-P-induced behavior in the mouse Eur. J. Pharmacol. 1992, 217, 197-201
    • (1992) Eur. J. Pharmacol. , vol.217 , pp. 197-201
    • Mousseau, D.D.1    Sun, X.F.2    Larson, A.A.3
  • 16
    • 0025513648 scopus 로고
    • Specific binding of substance P aminoterminal heptapeptide [SP(1-7)] to mouse brain and spinal cord membranes
    • Igwe, O. J.; Kim, D. C.; Seybold, V. S.; Larson, A. A. Specific binding of substance P aminoterminal heptapeptide [SP(1-7)] to mouse brain and spinal cord membranes J. Neurosci. 1990, 10, 3653-3663
    • (1990) J. Neurosci. , vol.10 , pp. 3653-3663
    • Igwe, O.J.1    Kim, D.C.2    Seybold, V.S.3    Larson, A.A.4
  • 17
    • 33645413849 scopus 로고    scopus 로고
    • Endomorphin-1 and endomorphin-2 differentially interact with specific binding sites for substance P (SP) aminoterminal SP1-7 in the rat spinal cord
    • Botros, M.; Hallberg, M.; Johansson, T.; Zhou, Q.; Lindeberg, G.; Frändberg, P.-A.; Toemboely, C.; Toth, G.; Le Greves, P.; Nyberg, F. Endomorphin-1 and endomorphin-2 differentially interact with specific binding sites for substance P (SP) aminoterminal SP1-7 in the rat spinal cord Peptides 2006, 27, 753-759
    • (2006) Peptides , vol.27 , pp. 753-759
    • Botros, M.1    Hallberg, M.2    Johansson, T.3    Zhou, Q.4    Lindeberg, G.5    Frändberg, P.-A.6    Toemboely, C.7    Toth, G.8    Le Greves, P.9    Nyberg, F.10
  • 18
    • 52049096834 scopus 로고    scopus 로고
    • Endomorphins interact with the substance P (SP) aminoterminal SP1-7 binding in the ventral tegmental area of the rat brain
    • Botros, M.; Johansson, T.; Zhou, Q.; Lindeberg, G.; Tomboly, C.; Toth, G.; Le Greves, P.; Nyberg, F.; Hallberg, M. Endomorphins interact with the substance P (SP) aminoterminal SP1-7 binding in the ventral tegmental area of the rat brain Peptides 2008, 29, 1820-1824
    • (2008) Peptides , vol.29 , pp. 1820-1824
    • Botros, M.1    Johansson, T.2    Zhou, Q.3    Lindeberg, G.4    Tomboly, C.5    Toth, G.6    Le Greves, P.7    Nyberg, F.8    Hallberg, M.9
  • 20
    • 0021690837 scopus 로고
    • Characterization of substance P(1-7) and (1-8) generating enzyme in human cerebrospinal fluid
    • Nyberg, F.; Le Greves, P.; Sundqvist, C.; Terenius, L. Characterization of substance P(1-7) and (1-8) generating enzyme in human cerebrospinal fluid Biochem. Biophys. Res. Commun. 1984, 125, 244-250
    • (1984) Biochem. Biophys. Res. Commun. , vol.125 , pp. 244-250
    • Nyberg, F.1    Le Greves, P.2    Sundqvist, C.3    Terenius, L.4
  • 21
    • 38549158455 scopus 로고    scopus 로고
    • Small peptides mimicking substance P (1-7) and encompassing a C-terminal amide functionality
    • Fransson, R.; Botros, M.; Nyberg, F.; Lindeberg, G.; Sandström, A.; Hallberg, M. Small peptides mimicking substance P (1-7) and encompassing a C-terminal amide functionality Neuropeptides 2008, 42, 31-37
    • (2008) Neuropeptides , vol.42 , pp. 31-37
    • Fransson, R.1    Botros, M.2    Nyberg, F.3    Lindeberg, G.4    Sandström, A.5    Hallberg, M.6
  • 24
    • 80055001170 scopus 로고    scopus 로고
    • The dipeptide Phe-Phe amide attenuates signs of hyperalgesia, allodynia and nociception in diabetic mice using a mechanism involving the sigma receptor system
    • Ohsawa, M.; Carlsson, A.; Asato, M.; Koizumi, T.; Nakanishi, Y.; Fransson, R.; Sandström, A.; Hallberg, M.; Nyberg, F.; Kamei, J. The dipeptide Phe-Phe amide attenuates signs of hyperalgesia, allodynia and nociception in diabetic mice using a mechanism involving the sigma receptor system Mol. Pain 2011, 7 (85) 1-12
    • (2011) Mol. Pain , vol.7 , Issue.85 , pp. 1-12
    • Ohsawa, M.1    Carlsson, A.2    Asato, M.3    Koizumi, T.4    Nakanishi, Y.5    Fransson, R.6    Sandström, A.7    Hallberg, M.8    Nyberg, F.9    Kamei, J.10
  • 25
    • 0028342648 scopus 로고
    • Utility of in-vitro drug-metabolism data in predicting in-vivo metabolic-clearance
    • Houston, J. B. Utility of in-vitro drug-metabolism data in predicting in-vivo metabolic-clearance Biochem. Pharmacol. 1994, 47, 1469-1479
    • (1994) Biochem. Pharmacol. , vol.47 , pp. 1469-1479
    • Houston, J.B.1
  • 26
    • 0032733974 scopus 로고    scopus 로고
    • Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: An examination of in vitro half-life approach and nonspecific binding to microsomes
    • Obach, R. S. Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: an examination of in vitro half-life approach and nonspecific binding to microsomes Drug Metab. Dispos. 1999, 27, 1350-1359
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 1350-1359
    • Obach, R.S.1
  • 27
    • 33748636018 scopus 로고    scopus 로고
    • Introduction to in vitro estimation of metabolic stability and drug interactions of new chemical entities in drug discovery and development
    • Baranczewski, P.; Stanczak, A.; Sundberg, K.; Svensson, R.; Wallin, A.; Jansson, J.; Garberg, P.; Postlind, H. Introduction to in vitro estimation of metabolic stability and drug interactions of new chemical entities in drug discovery and development Pharmacol. Rep. 2006, 58, 453-472
    • (2006) Pharmacol. Rep. , vol.58 , pp. 453-472
    • Baranczewski, P.1    Stanczak, A.2    Sundberg, K.3    Svensson, R.4    Wallin, A.5    Jansson, J.6    Garberg, P.7    Postlind, H.8
  • 28
    • 38449084547 scopus 로고    scopus 로고
    • Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers
    • Hubatsch, I.; Ragnarsson, E. G. E.; Artursson, P. Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers Nat. Protoc. 2007, 2, 2111-2119
    • (2007) Nat. Protoc. , vol.2 , pp. 2111-2119
    • Hubatsch, I.1    Ragnarsson, E.G.E.2    Artursson, P.3
  • 30
    • 84879590460 scopus 로고    scopus 로고
    • version 3.1; Schrödinger, LLC: New York, NY
    • Phase, version 3.1; Schrödinger, LLC: New York, NY, 2009.
    • (2009) Phase
  • 31
    • 0020319907 scopus 로고
    • Use of substance-P fragments to differentiate substance-P receptors of different tissues
    • Piercey, M. F.; Dobry, P. J. K.; Einspahr, F. J.; Schroeder, L. A.; Masiques, N. Use of substance-P fragments to differentiate substance-P receptors of different tissues Regul. Pept. 1982, 3, 337-349
    • (1982) Regul. Pept. , vol.3 , pp. 337-349
    • Piercey, M.F.1    Dobry, P.J.K.2    Einspahr, F.J.3    Schroeder, L.A.4    Masiques, N.5
  • 32
    • 0027213668 scopus 로고
    • Sequence-specific effects of neurokinin substance P on memory, reinforcement, and brain dopamine activity
    • Huston, J. P.; Hasenoehrl, R. U.; Boix, F.; Gerhardt, P.; Schwarting, R. K. W. Sequence-specific effects of neurokinin substance P on memory, reinforcement, and brain dopamine activity Psychopharmacology 1993, 112, 147-162
    • (1993) Psychopharmacology , vol.112 , pp. 147-162
    • Huston, J.P.1    Hasenoehrl, R.U.2    Boix, F.3    Gerhardt, P.4    Schwarting, R.K.W.5
  • 33
    • 0030888028 scopus 로고    scopus 로고
    • Long-lasting mnemotropic effect of substance P and its N-terminal fragment (SP1-7) on avoidance learning
    • Tomaz, C.; Silva, A. C.; Nogueira, P. J. Long-lasting mnemotropic effect of substance P and its N-terminal fragment (SP1-7) on avoidance learning Braz. J. Med. Biol. Res. 1997, 30, 231-233
    • (1997) Braz. J. Med. Biol. Res. , vol.30 , pp. 231-233
    • Tomaz, C.1    Silva, A.C.2    Nogueira, P.J.3
  • 34
    • 0026766974 scopus 로고
    • Constrained peptides: Models of bioactive peptides and protein substructures
    • Rizo, J.; Gierasch, L. M. Constrained peptides: models of bioactive peptides and protein substructures Annu. Rev. Biochem. 1992, 61, 387-418
    • (1992) Annu. Rev. Biochem. , vol.61 , pp. 387-418
    • Rizo, J.1    Gierasch, L.M.2
  • 35
    • 0016842581 scopus 로고
    • Alpha-Methyl amino acids. Resolution and amino protection
    • Turk, J.; Panse, G. T.; Marshall, G. R. alpha-Methyl amino acids. Resolution and amino protection J. Org. Chem. 1975, 40, 953-955
    • (1975) J. Org. Chem. , vol.40 , pp. 953-955
    • Turk, J.1    Panse, G.T.2    Marshall, G.R.3
  • 37
    • 0030610607 scopus 로고    scopus 로고
    • Beta-Methylation of the Phe(7) and Trp(9) melanotropin side chain pharmacophores affects ligand-receptor interactions and prolonged biological activity
    • Haskell-Luevano, C.; Toth, K.; Boteju, L.; Job, C.; Castrucci, A. M. D.; Hadley, M. E.; Hruby, V. J. beta-Methylation of the Phe(7) and Trp(9) melanotropin side chain pharmacophores affects ligand-receptor interactions and prolonged biological activity J. Med. Chem. 1997, 40, 2740-2749
    • (1997) J. Med. Chem. , vol.40 , pp. 2740-2749
    • Haskell-Luevano, C.1    Toth, K.2    Boteju, L.3    Job, C.4    Castrucci, A.M.D.5    Hadley, M.E.6    Hruby, V.J.7
  • 38
    • 68149161029 scopus 로고    scopus 로고
    • Transport of drugs by proton-coupled peptide transporters: Pearls and pitfalls
    • Brandsch, M. Transport of drugs by proton-coupled peptide transporters: pearls and pitfalls Expert Opin. Drug Metab. 2009, 5, 887-905
    • (2009) Expert Opin. Drug Metab. , vol.5 , pp. 887-905
    • Brandsch, M.1
  • 39
    • 0036018543 scopus 로고    scopus 로고
    • Transport of peptidomimetic drugs by the intestinal di/tri-peptide transporter, PepT1
    • Brodin, B.; Nielsen, C. U.; Steffansen, B.; Frokjaer, S. Transport of peptidomimetic drugs by the intestinal di/tri-peptide transporter, PepT1 Pharmacol. Toxicol. 2002, 90, 285-296
    • (2002) Pharmacol. Toxicol. , vol.90 , pp. 285-296
    • Brodin, B.1    Nielsen, C.U.2    Steffansen, B.3    Frokjaer, S.4
  • 41
    • 0036710840 scopus 로고    scopus 로고
    • Mammalian peptide transporters as targets for drug delivery
    • Rubio-Aliaga, I.; Daniel, H. Mammalian peptide transporters as targets for drug delivery Trends Pharmacol. Sci. 2002, 23, 434-440
    • (2002) Trends Pharmacol. Sci. , vol.23 , pp. 434-440
    • Rubio-Aliaga, I.1    Daniel, H.2
  • 42
    • 0842304421 scopus 로고    scopus 로고
    • Phe-Gly dipeptidomimetics designed for the di-/tripeptide transporters PEPT1 and PEPT2: Synthesis and biological investigations
    • VaÌŠbenö, J.; Lejon, T.; Nielsen, C. U.; Steffansen, B.; Chen, W. Q.; Hui, O. Y.; Borchardt, R. T.; Luthman, K. Phe-Gly dipeptidomimetics designed for the di-/tripeptide transporters PEPT1 and PEPT2: synthesis and biological investigations J. Med. Chem. 2004, 47, 1060-1069
    • (2004) J. Med. Chem. , vol.47 , pp. 1060-1069
    • Vaìšbenö, J.1    Lejon, T.2    Nielsen, C.U.3    Steffansen, B.4    Chen, W.Q.5    Hui, O.Y.6    Borchardt, R.T.7    Luthman, K.8
  • 44
    • 70350062194 scopus 로고    scopus 로고
    • Chemical and enzymatic stability of amino acid prodrugs containing methoxy, ethoxy and propylene glycol linkers
    • Gupta, D.; Gupta, S. V.; Lee, K. D.; Amidon, G. L. Chemical and enzymatic stability of amino acid prodrugs containing methoxy, ethoxy and propylene glycol linkers Mol. Pharmaceutics 2009, 6, 1604-1611
    • (2009) Mol. Pharmaceutics , vol.6 , pp. 1604-1611
    • Gupta, D.1    Gupta, S.V.2    Lee, K.D.3    Amidon, G.L.4
  • 49
    • 84879562429 scopus 로고    scopus 로고
    • version 9.0; Schrödinger, LLC: New York, NY
    • Maestro, version 9.0; Schrödinger, LLC: New York, NY, 2009.
    • (2009) Maestro
  • 50
    • 0035913529 scopus 로고    scopus 로고
    • Evaluation and reparametrization of the OPLS-AA force field for proteins via comparison with accurate quantum chemical calculations on peptides
    • Kaminski, G. A.; Friesner, R. A.; Tirado-Rives, J.; Jorgensen, W. L. Evaluation and reparametrization of the OPLS-AA force field for proteins via comparison with accurate quantum chemical calculations on peptides J. Phys. Chem. B 2001, 105, 6474-6487
    • (2001) J. Phys. Chem. B , vol.105 , pp. 6474-6487
    • Kaminski, G.A.1    Friesner, R.A.2    Tirado-Rives, J.3    Jorgensen, W.L.4
  • 51
    • 0344778061 scopus 로고
    • Semianalytical treatment of solvation for molecular mechanics and dynamics
    • Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. Semianalytical treatment of solvation for molecular mechanics and dynamics J. Am. Chem. Soc. 1990, 112, 6127-6129
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6127-6129
    • Still, W.C.1    Tempczyk, A.2    Hawley, R.C.3    Hendrickson, T.4


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