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Volumn 55, Issue 7, 2012, Pages 3027-3035

The cis-4-amino-l-proline residue as a scaffold for the synthesis of cyclic and linear endomorphin-2 analogues

Author keywords

[No Author keywords available]

Indexed keywords

CIS 4 AMINO PROLINE; DELTA OPIATE RECEPTOR; ENDOMORPHIN 2; KAPPA OPIATE RECEPTOR; MOLECULAR SCAFFOLD; MU OPIATE RECEPTOR; PROLINE; TETRAPEPTIDE; UNCLASSIFIED DRUG;

EID: 84859804704     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201402v     Document Type: Article
Times cited : (42)

References (46)
  • 1
    • 0030933655 scopus 로고    scopus 로고
    • A potent and selective endogenous agonist for the μ-opiate receptor
    • Zadina, J. E.; Hackler, L.; Ge, L. J.; Kastin, A. J. A potent and selective endogenous agonist for the μ-opiate receptor Nature 1997, 386, 499-502
    • (1997) Nature , vol.386 , pp. 499-502
    • Zadina, J.E.1    Hackler, L.2    Ge, L.J.3    Kastin, A.J.4
  • 5
    • 0020583961 scopus 로고
    • Minireview. Peptides and the blood-brain barrier
    • Meisenberg, G.; Simmons, W. H. Minireview. Peptides and the blood-brain barrier Life Sci. 1983, 32, 2611-2623
    • (1983) Life Sci. , vol.32 , pp. 2611-2623
    • Meisenberg, G.1    Simmons, W.H.2
  • 6
    • 0029871091 scopus 로고    scopus 로고
    • The blood-brain barrier: Principles for targeting peptides and drugs to the central nervous system
    • Begley, D. J. The blood-brain barrier: principles for targeting peptides and drugs to the central nervous system J. Pharm. Pharmacol. 1996, 48, 136-146
    • (1996) J. Pharm. Pharmacol. , vol.48 , pp. 136-146
    • Begley, D.J.1
  • 7
    • 0033537291 scopus 로고    scopus 로고
    • Modulation of endomorphin-2-induced analgesia by dipeptidyl peptidase IV
    • Shane, R.; Wilk, S.; Bodnar, R. J. Modulation of endomorphin-2-induced analgesia by dipeptidyl peptidase IV Brain Res. 1999, 815, 278-286
    • (1999) Brain Res. , vol.815 , pp. 278-286
    • Shane, R.1    Wilk, S.2    Bodnar, R.J.3
  • 8
    • 0033619675 scopus 로고    scopus 로고
    • Dipeptidyl-peptidase IV (CD26)-role in the inactivation of regulatory peptides
    • Mentlein, R. Dipeptidyl-peptidase IV (CD26)-role in the inactivation of regulatory peptides Regul. Pept. 1999, 85, 9-24
    • (1999) Regul. Pept. , vol.85 , pp. 9-24
    • Mentlein, R.1
  • 9
    • 0036711009 scopus 로고    scopus 로고
    • In vitro quantitative study of the degradation of endomorphins
    • Tomboly, C.; Peter, A.; Toth, G. In vitro quantitative study of the degradation of endomorphins Peptides 2002, 23, 1573-1580
    • (2002) Peptides , vol.23 , pp. 1573-1580
    • Tomboly, C.1    Peter, A.2    Toth, G.3
  • 11
    • 0026357733 scopus 로고
    • Development of opioid peptide analogs as pharmacologic tools and as potential drugs: Current status and future directions
    • (Emerging Technologies and New Directions in Drug Abuse Research, Vol.)
    • Schiller, P. W. Development of opioid peptide analogs as pharmacologic tools and as potential drugs: Current status and future directions. NIDA Research Monographs (Emerging Technologies and New Directions in Drug Abuse Research, Vol. 112), 1991, pp 180-197.
    • (1991) NIDA Research Monographs , vol.112 , pp. 180-197
    • Schiller, P.W.1
  • 12
    • 0001079639 scopus 로고
    • Development of receptor-selective opioid peptide analogs as pharmacologic tools and as potential drugs
    • Schiller, P. W. Development of receptor-selective opioid peptide analogs as pharmacologic tools and as potential drugs Handb. Exp. Pharmacol. 1993, 104/1 (opioids I) 681-710
    • (1993) Handb. Exp. Pharmacol. , vol.1041 , Issue.OPIOIDS I , pp. 681-710
    • Schiller, P.W.1
  • 13
    • 0033495881 scopus 로고    scopus 로고
    • Conformation-activity relationships of opioid peptides with selective activities at opioid receptors
    • Hruby, V. J.; Agnes, R. S. Conformation-activity relationships of opioid peptides with selective activities at opioid receptors Biopolymers 1999, 51, 391-410
    • (1999) Biopolymers , vol.51 , pp. 391-410
    • Hruby, V.J.1    Agnes, R.S.2
  • 14
    • 0033851469 scopus 로고    scopus 로고
    • Conformational and topographical considerations in designing agonist peptidomimetics from peptide leads
    • Hruby, V. J.; Balse, P. M. Conformational and topographical considerations in designing agonist peptidomimetics from peptide leads Curr. Med. Chem. 2000, 7, 945-970
    • (2000) Curr. Med. Chem. , vol.7 , pp. 945-970
    • Hruby, V.J.1    Balse, P.M.2
  • 18
    • 15044364083 scopus 로고    scopus 로고
    • Structure-activity relationship of the novel bivalent and C-terminal modified analogues of endomorphin-2
    • Gao, Y.; Liu, X.; Wei, J.; Zhu, B.; Chen, Q.; Wang, R. Structure-activity relationship of the novel bivalent and C-terminal modified analogues of endomorphin-2 Bioorg. Med. Chem. Lett. 2005, 15, 1847-1850
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 1847-1850
    • Gao, Y.1    Liu, X.2    Wei, J.3    Zhu, B.4    Chen, Q.5    Wang, R.6
  • 19
    • 77954721438 scopus 로고    scopus 로고
    • N-(tert)-butyloxycarbonyl-β,β-cyclopentyl-cysteine (acetamidomethyl)-methyl ester for synthesis of novel peptidomimetic derivatives
    • Mollica, A.; Feliciani, F.; Stefanucci, A.; Cacciatore, I.; Cornacchia, C.; Torino, D.; Pinnen, F. N-(tert)-butyloxycarbonyl-β,β-cyclopentyl- cysteine (acetamidomethyl)-methyl ester for synthesis of novel peptidomimetic derivatives Protein Pept. Lett. 2010, 17, 925-929
    • (2010) Protein Pept. Lett. , vol.17 , pp. 925-929
    • Mollica, A.1    Feliciani, F.2    Stefanucci, A.3    Cacciatore, I.4    Cornacchia, C.5    Torino, D.6    Pinnen, F.7
  • 20
    • 79954580560 scopus 로고    scopus 로고
    • Synthesis of (S)-5,6-dibromo-tryptophan derivatives as building blocks for peptide chemistry
    • Mollica, A.; Stefanucci, A.; Feliciani, F.; Lucente, G.; Pinnen, F. Synthesis of (S)-5,6-dibromo-tryptophan derivatives as building blocks for peptide chemistry Tetrahedron Lett. 2011, 52, 2583-2585
    • (2011) Tetrahedron Lett. , vol.52 , pp. 2583-2585
    • Mollica, A.1    Stefanucci, A.2    Feliciani, F.3    Lucente, G.4    Pinnen, F.5
  • 21
    • 0028100316 scopus 로고
    • 5]Enkephalin. A Highly Potent, Delta Opioid Receptor Selective Compound: Comparisons with Proposed Solution Conformations
    • 5]Enkephalin. A Highly Potent, Delta Opioid Receptor Selective Compound: Comparisons with Proposed Solution Conformations J. Am. Chem. Soc. 1994, 116, 7523-7531
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7523-7531
    • Flippen-Anderson, J.L.1    Hruby, V.J.2    Collins, N.3    George, C.4    Cudney, B.5
  • 22
    • 0037187386 scopus 로고    scopus 로고
    • Design, synthesis, and evaluation of opioid analogues with nonpeptidic β-turn scaffold:enkephalin and endomorphin mimetics
    • Eguchi, M.; Shen, R. W.; Shea, J. P.; Lee, M. S.; Kahn, M. Design, synthesis, and evaluation of opioid analogues with nonpeptidic β-turn scaffold:enkephalin and endomorphin mimetics J. Med. Chem. 2002, 45, 1395-1398
    • (2002) J. Med. Chem. , vol.45 , pp. 1395-1398
    • Eguchi, M.1    Shen, R.W.2    Shea, J.P.3    Lee, M.S.4    Kahn, M.5
  • 23
    • 0025974617 scopus 로고
    • Simulation of the structure and dynamics of the bis(penicillamine) enkephalin zwitterion
    • Smith, P. E.; Dang, L. X.; Pettitt, B. M. Simulation of the structure and dynamics of the bis(penicillamine) enkephalin zwitterion J. Am. Chem. Soc. 1991, 113, 67-73
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 67-73
    • Smith, P.E.1    Dang, L.X.2    Pettitt, B.M.3
  • 24
    • 0018144087 scopus 로고
    • Conformation of [Leu-5]-enkephalin from X-ray diffraction: Features important for recognition at opiate receptor
    • Smith, G. D.; Griffin, J. F. Conformation of [Leu-5]-enkephalin from X-ray diffraction: features important for recognition at opiate receptor Science 1978, 199, 1214-1216
    • (1978) Science , vol.199 , pp. 1214-1216
    • Smith, G.D.1    Griffin, J.F.2
  • 25
    • 0025195555 scopus 로고
    • Conformational preferences of [Leu-5]enkephalin in biomimetic media. Investigation by proton
    • Picone, D.; D'Ursi, A.; Motta, A.; Tancredi, T.; Temessi, P. A. Conformational preferences of [Leu-5]enkephalin in biomimetic media. Investigation by proton Eur. J. Biochem. 1990, 192, 433-439
    • (1990) Eur. J. Biochem. , vol.192 , pp. 433-439
    • Picone, D.1    D'Ursi, A.2    Motta, A.3    Tancredi, T.4    Temessi, P.A.5
  • 27
    • 0037147766 scopus 로고    scopus 로고
    • Synthesis and biological activities of YkFA analogues: Effects of position 4 substitutions and altered ring size on in vitro opioid activity
    • Burden, J. E.; Davis, P.; Porreca, F.; Spatola, A. F. Synthesis and biological activities of YkFA analogues: effects of position 4 substitutions and altered ring size on in vitro opioid activity Bioorg. Med. Chem. Lett. 2002, 12, 213-216
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 213-216
    • Burden, J.E.1    Davis, P.2    Porreca, F.3    Spatola, A.F.4
  • 30
    • 34347270982 scopus 로고    scopus 로고
    • Synthesis of stable and potent δ/μ opioid peptides: Analogues of H-Tyr- c [ d -Cys-Gly-Phe- d -Cys]-OH by ring-closing-metathesis
    • Mollica, A.; Guardiani, G.; Davis, P; Ma, S.-W.; Porreca, F.; Lai, J.; Mannina, L.; Sobolev, A. P.; Hruby, V. J. Synthesis of stable and potent δ/μ opioid peptides: Analogues of H-Tyr- c [ d -Cys-Gly-Phe- d -Cys]-OH by ring-closing-metathesis J. Med. Chem. 2007, 50, 3138-3142
    • (2007) J. Med. Chem. , vol.50 , pp. 3138-3142
    • Mollica, A.1    Guardiani, G.2    Davis, P.3    Ma, S.-W.4    Porreca, F.5    Lai, J.6    Mannina, L.7    Sobolev, A.P.8    Hruby, V.J.9
  • 31
    • 4744353375 scopus 로고    scopus 로고
    • Synthesis and Evaluation of the Affinity toward μ-Opioid Receptors of Atypical, Lipophilic Ligands Based on the Sequence c [Tyr-Pro-Trp-Phe-Gly]
    • Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Spinosa, R.; Calienni, M.; Quasem, A. R.; Spampinato, S. Synthesis and Evaluation of the Affinity toward μ-Opioid Receptors of Atypical, Lipophilic Ligands Based on the Sequence c [Tyr-Pro-Trp-Phe-Gly] J. Med. Chem. 2004, 47, 5198-5203
    • (2004) J. Med. Chem. , vol.47 , pp. 5198-5203
    • Cardillo, G.1    Gentilucci, L.2    Tolomelli, A.3    Spinosa, R.4    Calienni, M.5    Quasem, A.R.6    Spampinato, S.7
  • 35
    • 57749189579 scopus 로고    scopus 로고
    • Novel chemotactic For-Met-Leu-Phe-OMe (fMLF-OMe) analogues based on Met residue replacement by 4-amino-proline scaffold: Synthesis and bioactivity
    • Torino, D.; Mollica, A.; Feliciani, F.; Spisani, S.; Lucente, G. Novel chemotactic For-Met-Leu-Phe-OMe (fMLF-OMe) analogues based on Met residue replacement by 4-amino-proline scaffold: Synthesis and bioactivity Bioog. Med. Chem. 2009, 17, 251-259
    • (2009) Bioog. Med. Chem. , vol.17 , pp. 251-259
    • Torino, D.1    Mollica, A.2    Feliciani, F.3    Spisani, S.4    Lucente, G.5
  • 36
    • 32844469956 scopus 로고    scopus 로고
    • Chemotactic peptides: FMLF-Ome analogues incorporating proline-methionine chimeras as N-terminal residue
    • Mollica, A.; Paglialunga Paradisi, M.; Varani, K.; Spisani, S.; Lucente, G. Chemotactic peptides: fMLF-Ome analogues incorporating proline-methionine chimeras as N-terminal residue Bioog. Med. Chem. 2006, 14, 2253-2265
    • (2006) Bioog. Med. Chem. , vol.14 , pp. 2253-2265
    • Mollica, A.1    Paglialunga Paradisi, M.2    Varani, K.3    Spisani, S.4    Lucente, G.5
  • 37
    • 0041475925 scopus 로고    scopus 로고
    • The cyclization of peptides and depsipeptides
    • Davies, J. S. The cyclization of peptides and depsipeptides J. Peptide Sci. 2003, 9, 471-501
    • (2003) J. Peptide Sci. , vol.9 , pp. 471-501
    • Davies, J.S.1
  • 39
    • 0033543486 scopus 로고    scopus 로고
    • Pseudo-prolines in cyclic peptides: Conformational stabilization of cyclo[Pro-Thr(Ï̂Me,MePro)-Pro]
    • Ruckle, T.; De Lavallaz, P.; Keller, M.; Dumy, P.; Mutter, M. Pseudo-prolines in cyclic peptides: conformational stabilization of cyclo[Pro-Thr(Ï̂Me,MePro)-Pro] Tetrahedron 1999, 55, 11281-11288
    • (1999) Tetrahedron , vol.55 , pp. 11281-11288
    • Ruckle, T.1    De Lavallaz, P.2    Keller, M.3    Dumy, P.4    Mutter, M.5
  • 40
    • 0033031920 scopus 로고    scopus 로고
    • 3-HGlu] in aqueous solution. A new class of enterobactin-type C3-symmetrical ligands?
    • 3-HGlu] in aqueous solution. A new class of enterobactin-type C3-symmetrical ligands? Helv. Chim. Acta 1999, 82, 957-962
    • (1999) Helv. Chim. Acta , vol.82 , pp. 957-962
    • Gademann, K.1    Seebach, D.2
  • 41
    • 0035183462 scopus 로고    scopus 로고
    • Synthesis of cyclo-β-tripeptides and their biological in vitro evaluation as antiproliferatives against the growth of human cancer cell lines
    • Gademann, K.; Seebach, D. Synthesis of cyclo-β-tripeptides and their biological in vitro evaluation as antiproliferatives against the growth of human cancer cell lines Helv. Chim. Acta 2001, 84, 2924-2937
    • (2001) Helv. Chim. Acta , vol.84 , pp. 2924-2937
    • Gademann, K.1    Seebach, D.2
  • 42
    • 0035638291 scopus 로고    scopus 로고
    • Synthesis and investigation of the reactive oxygen species of a novel cyclic peptide-2,6-dimethoxyhydroquinone-3-mercaptoacetic acid conjugate
    • Song, Y. F.; Zhen, H. M. Synthesis and investigation of the reactive oxygen species of a novel cyclic peptide-2,6-dimethoxyhydroquinone-3- mercaptoacetic acid conjugate Chin. Chem. Lett. 2001, 12, 1075-1078
    • (2001) Chin. Chem. Lett. , vol.12 , pp. 1075-1078
    • Song, Y.F.1    Zhen, H.M.2
  • 45
    • 0027988826 scopus 로고
    • Pharmacological characterization of the cloned kappa opioid receptor as a kappa 1 b subtype
    • Lai, J.; Ma, S.-W.; Zhu, R.-H.; Rothman, R. B.; Lentes, K. U.; Porreca, F. Pharmacological characterization of the cloned kappa opioid receptor as a kappa 1 b subtype NeuroReport 1994, 5, 2161-2164
    • (1994) NeuroReport , vol.5 , pp. 2161-2164
    • Lai, J.1    Ma, S.-W.2    Zhu, R.-H.3    Rothman, R.B.4    Lentes, K.U.5    Porreca, F.6


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