메뉴 건너뛰기




Volumn 16, Issue 9, 2010, Pages 486-495

Introduction of lipidization - cationization motifs affords systemically bioavailable neuropeptide Y and neurotensin analogs with anticonvulsant activities

Author keywords

Bioavailability; Blood brain barrier; Chemical modifications; Epilepsy; Neurotensin; NPY

Indexed keywords

NEUROPEPTIDE Y DERIVATIVE; NEUROTENSIN DERIVATIVE; NPY BBB 2; NT BBB 1; UNCLASSIFIED DRUG;

EID: 77957293457     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1266     Document Type: Article
Times cited : (22)

References (50)
  • 2
    • 62749187793 scopus 로고    scopus 로고
    • Glycosylated neurotensin analogues exhibit sub-picomolar anticonvulsant potency in a pharmacoresistant model of epilepsy
    • Lee H-K, Zhang L, Smith MD, White HS, Bulaj G. Glycosylated neurotensin analogues exhibit sub-picomolar anticonvulsant potency in a pharmacoresistant model of epilepsy. Chem. Med. Chem. 2009; 4: 400-405.
    • (2009) Chem. Med. Chem. , vol.4 , pp. 400-405
    • Lee, H.-K.1    Zhang, L.2    Smith, M.D.3    White, H.S.4    Bulaj, G.5
  • 3
    • 9644257251 scopus 로고    scopus 로고
    • Galanin and galanin receptors in epilepsy
    • Mazarati AM. Galanin and galanin receptors in epilepsy. Neuropeptides 2004; 38: 331-343.
    • (2004) Neuropeptides , vol.38 , pp. 331-343
    • Mazarati, A.M.1
  • 6
    • 0030726198 scopus 로고    scopus 로고
    • Bioavailability and transport of peptides and peptide drugs into the brain
    • DOI 10.1016/S0196-9781(97)00242-8, PII S0196978197002428
    • Egleton RD, Davis TP. Bioavailability and transport of peptides and peptide drugs into the brain. Peptides 1997; 18: 1431-1439. (Pubitemid 27519756)
    • (1997) Peptides , vol.18 , Issue.9 , pp. 1431-1439
    • Egleton, R.D.1    Davis, T.P.2
  • 7
    • 0034031434 scopus 로고    scopus 로고
    • Molecular characterization of the ligand - receptor interaction of the neuropeptide Y family
    • Cabrele C, Beck-Sickinger AG. Molecular characterization of the ligand - receptor interaction of the neuropeptide Y family. J. Pept. Sci. 2000; 6: 97-122.
    • (2000) J. Pept. Sci. , vol.6 , pp. 97-122
    • Cabrele, C.1    Beck-Sickinger, A.G.2
  • 9
    • 35348861932 scopus 로고    scopus 로고
    • Adeno-associated virus-mediated expression and constitutive secretion of NPY or NPY13-36 suppresses activity in vivo
    • Foti S, Haberman RP, Samulski RJ, McCown TJ. Adeno-associated virus-mediated expression and constitutive secretion of NPY or NPY13-36 suppresses activity in vivo. Gene Ther. 2007; 14: 1534-1536.
    • (2007) Gene Ther. , vol.14 , pp. 1534-1536
    • Foti, S.1    Haberman, R.P.2    Samulski, R.J.3    McCown, T.J.4
  • 11
    • 0028097051 scopus 로고
    • Complete L-alanine scan of neuropeptide Y reveals ligands binding to Y1 and Y2 receptors with distinguished conformations
    • Beck-Sickinger AG, Wieland HA, Wittneben H, Willim K-D, Rudolf K, Jung G. Complete L-alanine scan of neuropeptide Y reveals ligands binding to Y1 and Y2 receptors with distinguished conformations. Eur. J. Biochem. 1994; 225: 947-957.
    • (1994) Eur. J. Biochem. , vol.225 , pp. 947-957
    • Beck-Sickinger, A.G.1    Wieland, H.A.2    Wittneben, H.3    Willim, K.-D.4    Rudolf, K.5    Jung, G.6
  • 12
    • 0028916226 scopus 로고
    • Structure - activity relationships of neuropeptide Y analogues with respect to Y1 and Y2 receptors
    • Beck-Sickinger AG, Jung G. Structure - activity relationships of neuropeptide Y analogues with respect to Y1 and Y2 receptors. Biopolymers 1995; 37: 123-142.
    • (1995) Biopolymers , vol.37 , pp. 123-142
    • Beck-Sickinger, A.G.1    Jung, G.2
  • 13
    • 0345598174 scopus 로고
    • Centrally truncated and stabilized porcine neuropeptide Y analogs: Design, synthesis, and mouse brain receptor binding
    • Krstenansky JL, Owen TJ, Buck SH, Hagaman KA, McLean LR. Centrally truncated and stabilized porcine neuropeptide Y analogs: design, synthesis, and mouse brain receptor binding. Proc. Natl. Acad. Sci. 1989; 86: 4377-4381.
    • (1989) Proc. Natl. Acad. Sci. , vol.86 , pp. 4377-4381
    • Krstenansky, J.L.1    Owen, T.J.2    Buck, S.H.3    Hagaman, K.A.4    McLean, L.R.5
  • 14
    • 0029361837 scopus 로고
    • A rational approach for the development of reduced-size analogues of neuropeptide Y with high affinity to the Y1 receptor
    • Rist B, Wieland HA, Willim K-D, Beck-Sickinger AG. A rational approach for the development of reduced-size analogues of neuropeptide Y with high affinity to the Y1 receptor. J. Pept. Sci. 1995; 1: 341-348.
    • (1995) J. Pept. Sci. , vol.1 , pp. 341-348
    • Rist, B.1    Wieland, H.A.2    Willim, K.-D.3    Beck-Sickinger, A.G.4
  • 16
    • 0026090295 scopus 로고
    • The effects of selective amino acid substitution upon neuropeptide Y antisecretory potency in rat jejunum mucosa
    • Cox HM, Krstenansky JL. The effects of selective amino acid substitution upon neuropeptide Y antisecretory potency in rat jejunum mucosa. Peptides 1991; 12: 323-327.
    • (1991) Peptides , vol.12 , pp. 323-327
    • Cox, H.M.1    Krstenansky, J.L.2
  • 17
    • 33748745844 scopus 로고    scopus 로고
    • Neurotensin: Role in psychiatric and neurological diseases
    • DOI 10.1016/j.peptides.2006.04.024, PII S0196978106002853
    • Cáceda R, Kinkead B, Nemeroff CB. Neurotensin: role in psychiatric and neurologic diseases. Peptides 2006; 27: 2385-2404. (Pubitemid 44402784)
    • (2006) Peptides , vol.27 , Issue.10 , pp. 2385-2404
    • Caceda, R.1    Kinkead, B.2    Nemeroff, C.B.3
  • 18
    • 33748754632 scopus 로고    scopus 로고
    • Bioactive analogs of neurotensin: Focus on CNS effects
    • Boules M, Fredrickson P, Richelson E. Bioactive analogs of neurotensin: focus on CNS effects. Peptides 2006; 27: 2523-2533.
    • (2006) Peptides , vol.27 , pp. 2523-2533
    • Boules, M.1    Fredrickson, P.2    Richelson, E.3
  • 19
    • 33748755106 scopus 로고    scopus 로고
    • Neurotensin and pain modulation
    • Dobner PR. Neurotensin and pain modulation. Peptides 2006; 27: 2405-2414.
    • (2006) Peptides , vol.27 , pp. 2405-2414
    • Dobner, P.R.1
  • 20
    • 0033555286 scopus 로고    scopus 로고
    • Transmitters involved in antinociception in the spinal chord
    • Fürst S. Transmitters involved in antinociception in the spinal chord. Brain Res. Bull. 1999; 48: 129-141.
    • (1999) Brain Res. Bull. , vol.48 , pp. 129-141
    • Fürst, S.1
  • 21
    • 0027159642 scopus 로고
    • A structure - affinity study of the amino acid side-chains of neurotensin: N and C terminal deletions and Ala-scan
    • Henry JA, Horwell DC, Meecham KG, Rees DC. A structure - affinity study of the amino acid side-chains of neurotensin: N and C terminal deletions and Ala-scan. Bioorg. Med. Chem. Lett. 1993; 3: 949-952.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 949-952
    • Henry, J.A.1    Horwell, D.C.2    Meecham, K.G.3    Rees, D.C.4
  • 23
    • 41149167204 scopus 로고    scopus 로고
    • Synthesis and biological effects of c(Lys-Lys-Pro-Tyr-Ile-Leu-Lys-Pro- Tyr-Ile-Leu) (JMV2012), a new analogue of neurotensin that crosses the blood - brain barrier
    • Bredeloux P, Cavelier F, Dubuc I, Vivet B, Costentin J, Martinez J. Synthesis and biological effects of c(Lys-Lys-Pro-Tyr-Ile-Leu-Lys-Pro- Tyr-Ile-Leu) (JMV2012), a new analogue of neurotensin that crosses the blood - brain barrier. J. Med. Chem. 2008; 51: 1610-1616.
    • (2008) J. Med. Chem. , vol.51 , pp. 1610-1616
    • Bredeloux, P.1    Cavelier, F.2    Dubuc, I.3    Vivet, B.4    Costentin, J.5    Martinez, J.6
  • 24
    • 0141567435 scopus 로고    scopus 로고
    • In vitro analysis of stable, receptor-selective neurotensin [813] analogs
    • Kokko KP, Hadden MK, Orwig KS, Mazella J, Dix TA. In vitro analysis of stable, receptor-selective neurotensin [8-13] analogs. J. Med. Chem. 2003; 46: 4141-4148.
    • (2003) J. Med. Chem. , vol.46 , pp. 4141-4148
    • Kokko, K.P.1    Hadden, M.K.2    Orwig, K.S.3    Mazella, J.4    Dix, T.A.5
  • 25
    • 64349115504 scopus 로고    scopus 로고
    • Synthesis and applications of polyamine amino acid residues: Improving the bioactivity of an analgesic neuropeptide, neurotensin
    • Zhang L, Lee H-K, Pruess TH, White HS, Bulaj G. Synthesis and applications of polyamine amino acid residues: improving the bioactivity of an analgesic neuropeptide, neurotensin. J. Med. Chem. 2009; 52: 1514-1517.
    • (2009) J. Med. Chem. , vol.52 , pp. 1514-1517
    • Zhang, L.1    Lee, H.-K.2    Pruess, T.H.3    White, H.S.4    Bulaj, G.5
  • 27
    • 64349112137 scopus 로고    scopus 로고
    • Structural requirements for a lipoamino acid in modulating the anticonvulsant activities of systemically active galanin analogues
    • Zhang L, Robertson CR, Green BR, Pruess TH, White HS, Bulaj G. Structural requirements for a lipoamino acid in modulating the anticonvulsant activities of systemically active galanin analogues. J.Med. Chem. 2009; 52: 1310-1316.
    • (2009) J.Med. Chem. , vol.52 , pp. 1310-1316
    • Zhang, L.1    Robertson, C.R.2    Green, B.R.3    Pruess, T.H.4    White, H.S.5    Bulaj, G.6
  • 28
    • 62949217659 scopus 로고    scopus 로고
    • Developing novel antiepileptic drugs: Characterization of NAX 5055, a systemically-active galanin analog, in epilepsy models
    • White HS, Scholl EA, Klein BD, Flynn SP, Pruess TH, Green BR, Zhang L, Bulaj G. Developing novel antiepileptic drugs: characterization of NAX 5055, a systemically-active galanin analog, in epilepsy models. Neurotherapeutics 2009; 6: 372-380.
    • (2009) Neurotherapeutics , vol.6 , pp. 372-380
    • White, H.S.1    Scholl, E.A.2    Klein, B.D.3    Flynn, S.P.4    Pruess, T.H.5    Green, B.R.6    Zhang, L.7    Bulaj, G.8
  • 29
    • 12344319635 scopus 로고    scopus 로고
    • Development of neuropeptide drugs that cross the blood - brain barrier
    • Egleton RD, Davis TP. Development of neuropeptide drugs that cross the blood - brain barrier. NeuroRx 2005; 2: 44-53.
    • (2005) NeuroRx , vol.2 , pp. 44-53
    • Egleton, R.D.1    Davis, T.P.2
  • 30
    • 33747300527 scopus 로고    scopus 로고
    • Internalization of cationic peptides: The road less (ormore?) traveled
    • Fuchs SM, Raines RT. Internalization of cationic peptides: the road less (ormore?) traveled. Cell.Mol. Life Sci. 2006; 63: 1819-1822.
    • (2006) Cell.Mol. Life Sci. , vol.63 , pp. 1819-1822
    • Fuchs, S.M.1    Raines, R.T.2
  • 31
    • 0042232110 scopus 로고    scopus 로고
    • Studies on the internalization mechanism of cationic cell-penetrating peptides
    • Drin G, Cottin S, Blanc E, Rees AR, Temsamani J. Studies on the internalization mechanism of cationic cell-penetrating peptides. J. Biol. Chem. 2003; 278: 31192-31201.
    • (2003) J. Biol. Chem. , vol.278 , pp. 31192-31201
    • Drin, G.1    Cottin, S.2    Blanc, E.3    Rees, A.R.4    Temsamani, J.5
  • 32
    • 0036001391 scopus 로고    scopus 로고
    • Structure - activity relationship of reversibly lipidized peptides: Studies of fatty acid-desmopressin conjugates
    • Wang J, Wu D, Shen WC. Structure - activity relationship of reversibly lipidized peptides: studies of fatty acid-desmopressin conjugates. Pharm. Res. 2002; 19: 609-614.
    • (2002) Pharm. Res. , vol.19 , pp. 609-614
    • Wang, J.1    Wu, D.2    Shen, W.C.3
  • 33
    • 0016169865 scopus 로고
    • Determination of the helix and beta form of proteins in aqueous solution by circular dichroism
    • Chen Y-H, Yang JT, Chau KH. Determination of the helix and beta form of proteins in aqueous solution by circular dichroism. Biochemistry 1974; 13: 3350-3359.
    • (1974) Biochemistry , vol.13 , pp. 3350-3359
    • Chen, Y.-H.1    Yang, J.T.2    Chau, K.H.3
  • 34
    • 0019871847 scopus 로고
    • Ordered conformation of polypeptides and proteins in acidic dodecylsulfate solution
    • Wu C-SC, Ikeda K, Yang JT. Ordered conformation of polypeptides and proteins in acidic dodecylsulfate solution. Biochemistry 1981; 20: 566-570.
    • (1981) Biochemistry , vol.20 , pp. 566-570
    • Wu, C.-S.C.1    Ikeda, K.2    Yang, J.T.3
  • 35
    • 0015861774 scopus 로고
    • Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50 percent inhibition (IC50) of an enzymatic reaction
    • Cheng Y-C, Prusoff WH. Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50 percent inhibition (IC50) of an enzymatic reaction. Biochem. Pharmacol. 1973; 22: 3099-3108.
    • (1973) Biochem. Pharmacol. , vol.22 , pp. 3099-3108
    • Cheng, Y.-C.1    Prusoff, W.H.2
  • 38
    • 50249124786 scopus 로고    scopus 로고
    • Toward and optimal blood - brain barrier shuttle by synthesis and evaluation of peptide libraries
    • Malakoutikhah M, Teixidó M, Giralt E. Toward and optimal blood - brain barrier shuttle by synthesis and evaluation of peptide libraries. J. Med. Chem. 2008; 51: 4881-4889.
    • (2008) J. Med. Chem. , vol.51 , pp. 4881-4889
    • Malakoutikhah, M.1    Teixidó, M.2    Giralt, E.3
  • 39
    • 34447544341 scopus 로고    scopus 로고
    • Albumin binding of short cationic antimicrobial micropeptides and its influence on the in vitro bactericidal effect
    • Svenson J, Brandsdal B, Stensen W, Svendsen JS. Albumin binding of short cationic antimicrobial micropeptides and its influence on the in vitro bactericidal effect. J. Med. Chem. 2007; 50: 3334-3339.
    • (2007) J. Med. Chem. , vol.50 , pp. 3334-3339
    • Svenson, J.1    Brandsdal, B.2    Stensen, W.3    Svendsen, J.S.4
  • 40
    • 0022521041 scopus 로고
    • Peptides bound to albumin
    • Manezo Y, Khatchadourian C. Peptides bound to albumin. Life Sci. 1986; 39: 1751-1753.
    • (1986) Life Sci. , vol.39 , pp. 1751-1753
    • Manezo, Y.1    Khatchadourian, C.2
  • 41
    • 77649219653 scopus 로고    scopus 로고
    • Engineering galanin analogues that discriminate between GalR1 and GalR2 subtypes and exhibit anticonvulsant activity following systemic delivery
    • Robertson CR, Scholl EA, Pruess TH, Green BR, White HS, Bulaj G. Engineering galanin analogues that discriminate between GalR1 and GalR2 subtypes and exhibit anticonvulsant activity following systemic delivery. J. Med. Chem. 2010; 53: 1871-1875.
    • (2010) J. Med. Chem. , vol.53 , pp. 1871-1875
    • Robertson, C.R.1    Scholl, E.A.2    Pruess, T.H.3    Green, B.R.4    White, H.S.5    Bulaj, G.6
  • 43
    • 27744477471 scopus 로고    scopus 로고
    • Design, synthesis, and evaluation of the antipsychotic potential of orally bioavailable neurotensin (813) analogues containing non-natural arginine and lysine residues
    • Hadden MK, Orwig KS, Kokko KP, Mazella J, Dix TA. Design, synthesis, and evaluation of the antipsychotic potential of orally bioavailable neurotensin (8-13) analogues containing non-natural arginine and lysine residues. Neuropharmacology 2005; 49: 1149-1159.
    • (2005) Neuropharmacology , vol.49 , pp. 1149-1159
    • Hadden, M.K.1    Orwig, K.S.2    Kokko, K.P.3    Mazella, J.4    Dix, T.A.5
  • 44
    • 36248946214 scopus 로고    scopus 로고
    • NPY Y1 and Y5 receptor selective antagonists as antiobesity drugs
    • MacNeil DS. NPY Y1 and Y5 receptor selective antagonists as antiobesity drugs. Curr. Top. Med. Chem. 2007; 7: 1721-1733.
    • (2007) Curr. Top. Med. Chem. , vol.7 , pp. 1721-1733
    • MacNeil, D.S.1
  • 46
    • 33751162429 scopus 로고    scopus 로고
    • Identification of bombesin receptor subtype-specific ligands: Effect of N-methyl scanning, truncation, substitution, and evaluation of putative reported selective ligands
    • Mantey SA, Gonzalez N, Schumann M, Pradhan TK, Shen L, Coy DH, Jensen RT. Identification of bombesin receptor subtype-specific ligands: effect of N-methyl scanning, truncation, substitution, and evaluation of putative reported selective ligands. J. Pharmacol. Exp. Ther. 2006; 319: 980-989.
    • (2006) J. Pharmacol. Exp. Ther. , vol.319 , pp. 980-989
    • Mantey, S.A.1    Gonzalez, N.2    Schumann, M.3    Pradhan, T.K.4    Shen, L.5    Coy, D.H.6    Jensen, R.T.7
  • 49
    • 0342726574 scopus 로고    scopus 로고
    • Structure - activity relationship studies on the novel neuropeptide orphanin FQ
    • Reinscheid RK, Ardati A, Frederick J, Monsma J, Civelli O. Structure - activity relationship studies on the novel neuropeptide orphanin FQ. J. Biol. Chem. 1996; 271: 14163-14168.
    • (1996) J. Biol. Chem. , vol.271 , pp. 14163-14168
    • Reinscheid, R.K.1    Ardati, A.2    Frederick, J.3    Monsma, J.4    Civelli, O.5
  • 50
    • 0036834372 scopus 로고    scopus 로고
    • Designing peptide receptor agonists and antagonists
    • Hruby VJ. Designing peptide receptor agonists and antagonists. Nat. Rev. Drug Discov. 2002; 1: 847-858.
    • (2002) Nat. Rev. Drug Discov. , vol.1 , pp. 847-858
    • Hruby, V.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.