메뉴 건너뛰기




Volumn 789, Issue , 2011, Pages 313-336

Prodrug Design for Brain Delivery of Small- and Medium-Sized Neuropeptides

Author keywords

Analeptic effect; Bioactivation; Blood brain barrier; Immobilized artificial membrane chromatography; Lipophilicity; Neuropeptide; Neuropharmacology; Prodrug; Solid phase peptide synthesis; Thyrotropin releasing hormone analogue

Indexed keywords

DRUG DERIVATIVE; NEUROPEPTIDE; PRODRUG; PROTIRELIN;

EID: 80054737357     PISSN: 10643745     EISSN: 19406029     Source Type: Book Series    
DOI: 10.1007/978-1-61779-310-3_21     Document Type: Chapter
Times cited : (13)

References (40)
  • 2
    • 33645553886 scopus 로고    scopus 로고
    • Targeting drugs into the central nervous system
    • Muzykantow, V.R., and Torchilin, V., Kluwer Academic Publishers, Dordrecht
    • Prokai, L. (2002) Targeting drugs into the central nervous system. In Muzykantow, V.R., and Torchilin, V. (eds) Biomedical aspects of drug targeting, Kluwer Academic Publishers, Dordrecht.
    • (2002) Biomedical Aspects of Drug Targeting
    • Prokai, L.1
  • 3
    • 0035253135 scopus 로고    scopus 로고
    • Efflux transport systems for drugs at the blood–brain barrier and blood–cerebrospinal fluid barrier (Part 1)
    • Kusuhara, H., and Sugiyama, Y. (2001) Efflux transport systems for drugs at the blood–brain barrier and blood–cerebrospinal fluid barrier (Part 1). Drug Discov. Today 6, 150–156.
    • (2001) Drug Discov. Today , vol.6 , pp. 150-156
    • Kusuhara, H.1    Sugiyama, Y.2
  • 4
    • 0141620181 scopus 로고    scopus 로고
    • Structural and functional aspects of the blood– brain barrier
    • Prokai, L., and Prokai-Tatrai, K, Birkhäuser, Basel
    • Begley, D.J., and Brightman, M.W. (2003) Structural and functional aspects of the blood– brain barrier. In: Prokai, L., and Prokai-Tatrai, K. (eds) Peptide transport and delivery into the central nervous system, Vol. 61, Birkhäuser, Basel.
    • (2003) Peptide Transport and Delivery into the Central Nervous System , vol.61
    • Begley, D.J.1    Brightman, M.W.2
  • 5
    • 0027404655 scopus 로고
    • Peptidases, peptides at the mammalian blood– brain barrier
    • Brownlees, J., and Williams, C.H. (1993) Peptidases, peptides at the mammalian blood– brain barrier. J. Neurochem. 60, 793–803.
    • (1993) J. Neurochem. , vol.60 , pp. 793-803
    • Brownlees, J.1    Williams, C.H.2
  • 6
    • 0036463371 scopus 로고    scopus 로고
    • Drug and gene targeting to the brain with molecular Trojan horses
    • Pardridge, W.J. (2002) Drug and gene targeting to the brain with molecular Trojan horses. Nature Rev. Drug Discovery 1, 131–139.
    • (2002) Nature Rev. Drug Discovery , vol.1 , pp. 131-139
    • Pardridge, W.J.1
  • 7
    • 0001199533 scopus 로고
    • Chemical aspects of selective toxicity
    • Albert, A, (1958) Chemical aspects of selective toxicity. Nature 182, 421–422.
    • (1958) Nature , vol.182 , pp. 421-422
    • Albert, A.1
  • 8
    • 0141508829 scopus 로고    scopus 로고
    • Modifying peptide properties by prodrug design for enhanced transport into the CNS
    • Prokai, L., and Prokai-Tatrai, K, Birkhäuser, Basel
    • Prokai-Tatrai, K., and Prokai, L. (2003) Modifying peptide properties by prodrug design for enhanced transport into the CNS. In: Prokai, L., and Prokai-Tatrai, K. (eds) Peptide transport and delivery into the central nervous system, Vol. 61, Birkhäuser, Basel.
    • (2003) Peptide Transport and Delivery into the Central Nervous System , vol.61
    • Prokai-Tatrai, K.1    Prokai, L.2
  • 9
    • 0034935071 scopus 로고    scopus 로고
    • Lipid, sugar and liposaccharide based delivery systems
    • Wong, A., and Toth, I. (2001) Lipid, sugar and liposaccharide based delivery systems. Curr. Med. Chem. 8, 1123–1136.
    • (2001) Curr. Med. Chem. , vol.8 , pp. 1123-1136
    • Wong, A.1    Toth, I.2
  • 10
    • 77956836899 scopus 로고
    • Peptide stability in drug development: In vitro peptide degradation in plasma and serum
    • Powell, M.F. (1993). Peptide stability in drug development: in vitro peptide degradation in plasma and serum. Ann. Rep. Med. Chem. 28, 285–294.
    • (1993) Ann. Rep. Med. Chem. , vol.28 , pp. 285-294
    • Powell, M.F.1
  • 13
    • 0030471676 scopus 로고    scopus 로고
    • Brain-targeted delivery of a leucine-enkephalin analogue by retrometabolic design
    • Prokai-Tatrai, K., and Prokai, L. (1996) Brain-targeted delivery of a leucine-enkephalin analogue by retrometabolic design. J. Med. Chem. 39, 4775–4782.
    • (1996) J. Med. Chem. , vol.39 , pp. 4775-4782
    • Prokai-Tatrai, K.1    Prokai, L.2
  • 14
    • 85056061153 scopus 로고    scopus 로고
    • The utility of oligopeptidase in brain-targeting deliver y of an enkephalin analogue by prodrug design
    • Prokai-Tatrai, K., Kim, H.S., and Prokai, L. (2008) The utility of oligopeptidase in brain-targeting deliver y of an enkephalin analogue by prodrug design. Open Med. Chem. J. 2, 97–100.
    • (2008) Open Med. Chem. J. , vol.2 , pp. 97-100
    • Prokai-Tatrai, K.1    Kim, H.S.2    Prokai, L.3
  • 15
    • 8644224096 scopus 로고    scopus 로고
    • Centrally acting and metabolically stable thyrotropin-releasing hormone analogues by replacement of histidine with substituted pyridinium
    • Prokai, L., Prokai-Tatrai, K., Zharikova, A.D. et al. (2004) Centrally acting and metabolically stable thyrotropin-releasing hormone analogues by replacement of histidine with substituted pyridinium. J. Med. Chem. 47, 625–6033.
    • (2004) J. Med. Chem. , vol.47 , pp. 625-6033
    • Prokai, L.1    Prokai-Tatrai, K.2    Zharikova, A.D.3
  • 16
    • 70350227204 scopus 로고    scopus 로고
    • Computational models for central nervous system penetration
    • Klon, A.E. (2009) Computational models for central nervous system penetration. Curr. Med. Chem. 5, 71–89.
    • (2009) Curr. Med. Chem. , vol.5 , pp. 71-89
    • Klon, A.E.1
  • 17
    • 0029947489 scopus 로고    scopus 로고
    • Methods for determining n-octanol-water partition constants
    • Danielsson, L.G., and Zhang, Y.H. (1996) Methods for determining n-octanol-water partition constants. TRAC–Trends Anal. Chem. 15, 188–196.
    • (1996) TRAC–Trends Anal. Chem. , vol.15 , pp. 188-196
    • Danielsson, L.G.1    Zhang, Y.H.2
  • 18
    • 0029991481 scopus 로고    scopus 로고
    • Immobilized-artificial-membrane chromatography: Measurements of membrane partition coefficient and predicting drug membrane permeability
    • Ong, S., Hanlan, C., and Pidgeon, J. (1996) Immobilized-artificial-membrane chromatography: Measurements of membrane partition coefficient and predicting drug membrane permeability. J. Chromatogr. 728, 13–128.
    • (1996) J. Chromatogr. , vol.728 , pp. 13-128
    • Ong, S.1    Hanlan, C.2    Pidgeon, J.3
  • 19
    • 60749111590 scopus 로고    scopus 로고
    • Artificial membrane assays to assess permeability
    • Faller, B. (2008) Artificial membrane assays to assess permeability. Curr. Drug Metab. 9, 886–892.
    • (2008) Curr. Drug Metab. , vol.9 , pp. 886-892
    • Faller, B.1
  • 20
    • 17444406065 scopus 로고    scopus 로고
    • Permeability studies on in vitro blood-brain barrier models: Physiology, pathology, and pharmacology
    • Deli, M.A., Abraham, C.S., Kataoka, Y. et al. (2005) Permeability studies on in vitro blood-brain barrier models: Physiology, pathology, and pharmacology. Cell Mol. Neurobiol. 25, 59–129.
    • (2005) Cell Mol. Neurobiol. , vol.25 , pp. 59-129
    • Deli, M.A.1    Abraham, C.S.2    Kataoka, Y.3
  • 21
    • 0016816747 scopus 로고
    • Analysis of brain uptake and loss of radiotracers after intracarotid injection
    • Bradbury, M.W.B., Patlak, C.S., and Oldendorf, W.H. (1975) Analysis of brain uptake and loss of radiotracers after intracarotid injection. Am. J. Physiol. 229, 1110–1115.
    • (1975) Am. J. Physiol. , vol.229 , pp. 1110-1115
    • Bradbury, M.W.B.1    Patlak, C.S.2    Oldendorf, W.H.3
  • 22
    • 0034534885 scopus 로고    scopus 로고
    • Exploratory pharmacokinetics and brain distribution study of a neuropeptide FF antagonist by liquid chromatography/atmospheric pressure ionization tandem mass spectrometry
    • Prokai, L., Zharikova, A.D., Janaky T et al. (2000) Exploratory pharmacokinetics and brain distribution study of a neuropeptide FF antagonist by liquid chromatography/atmospheric pressure ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom. 14, 2412–2418.
    • (2000) Rapid Commun. Mass Spectrom. , vol.14 , pp. 2412-2418
    • Prokai, L.1    Zharikova, A.D.2    Janaky, T.3
  • 23
    • 0015545469 scopus 로고
    • Lipophilic character and biological-activity of drugs. 2. Parabolic case
    • Hansch, C., and Clayton, J.M. (1973) Lipophilic character and biological-activity of drugs. 2. Parabolic case. J. Pharm. Sci. 62, 1–21.
    • (1973) J. Pharm. Sci. , vol.62 , pp. 1-21
    • Hansch, C.1    Clayton, J.M.2
  • 24
    • 34250744722 scopus 로고    scopus 로고
    • Central ner vous system drug disposition: The relationship between in situ brain permeability and brain free fraction
    • Summerfield, S.G., Read, K., Begley, D.J. et al.(2007) Central ner vous system drug disposition: The relationship between in situ brain permeability and brain free fraction. J. Pharmacol. Exp. Ther. 322, 205–213.
    • (2007) J. Pharmacol. Exp. Ther. , vol.322 , pp. 205-213
    • Summerfield, S.G.1    Read, K.2    Begley, D.J.3
  • 25
    • 0025681432 scopus 로고
    • Distribution of pyroglutamylpeptide amides related to thyrotropin-releasing hormone in the central nervous system and periphery of the rat
    • Del Rio-Garcia, J., and Smyth, D.G. (1990) Distribution of pyroglutamylpeptide amides related to thyrotropin-releasing hormone in the central nervous system and periphery of the rat. J. Endocrinol. 127, 445–450.
    • (1990) J. Endocrinol. , vol.127 , pp. 445-450
    • Del Rio-Garcia, J.1    Smyth, D.G.2
  • 26
    • 0036389891 scopus 로고    scopus 로고
    • Central nervous system effects of thyrotropin-releasing hormone and its analogues: Opportunities and perspectives for drug discovery and development
    • Jucker, E.M, Birkhäuser, Basel
    • Prokai, L. (2002) Central nervous system effects of thyrotropin-releasing hormone and its analogues: opportunities and perspectives for drug discovery and development. In: Jucker, E.M. (ed) Progress in drug research, Vol 59, Birkhäuser, Basel.
    • (2002) Progress in Drug Research , vol.59
    • Prokai, L.1
  • 27
    • 61449207912 scopus 로고    scopus 로고
    • Prodrugs of thyrotropin-releasing hormone and related peptides as central nervous system agents
    • Prokai-Tatrai, K., Prokai, L. (2009) Prodrugs of thyrotropin-releasing hormone and related peptides as central nervous system agents. Molecules 14, 633–654.
    • (2009) Molecules , vol.14 , pp. 633-654
    • Prokai-Tatrai, K.1    Prokai, L.2
  • 28
    • 0034596063 scopus 로고    scopus 로고
    • Kinetic investigation of the specificity of porcine brain thyrotropin-releasing hormone-degrading ectoenzyme for thyrotropin-releasing hormone-like peptides
    • Kelly, J.A., Slator, G.R., Tipton, K.F. et al. (2000) Kinetic investigation of the specificity of porcine brain thyrotropin-releasing hormone-degrading ectoenzyme for thyrotropin-releasing hormone-like peptides. J. Biol. Chem. 275, 16746–16751.
    • (2000) J. Biol. Chem. , vol.275 , pp. 16746-16751
    • Kelly, J.A.1    Slator, G.R.2    Tipton, K.F.3
  • 30
    • 77952302074 scopus 로고    scopus 로고
    • 2]TRH dose-dependently attenuates TRH-evoked analeptic effect in the mouse brain
    • 2]TRH dose-dependently attenuates TRH-evoked analeptic effect in the mouse brain. Brain Res. Bull. 82, 83–86.
    • (2010) Brain Res. Bull , vol.82 , pp. 83-86
    • Nguyen, V.1    Zharikova, A.D.2    Prokai-Tatrai, K.3
  • 31
    • 20744456789 scopus 로고
    • Solid phase peptide synthesis. Synthesis of a tetrapeptide
    • Merrifield, R.B. (1963) Solid phase peptide synthesis. Synthesis of a tetrapeptide. J. Am. Chem. Soc. 85, 2149–2154.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2149-2154
    • Merrifield, R.B.1
  • 32
    • 33947091567 scopus 로고
    • 9-Fluorenylmethoxycarbonyl amino-protecting group
    • Carpino, L.A., and Han, G.Y. (1972) 9-Fluorenylmethoxycarbonyl amino-protecting group. J. Org. Chem. 37, 3404–3409.
    • (1972) J. Org. Chem. , vol.37 , pp. 3404-3409
    • Carpino, L.A.1    Han, G.Y.2
  • 33
    • 0032567305 scopus 로고    scopus 로고
    • Use of onium salt-based coupling reagents in peptide synthesis
    • Albericio, F., Bofill, J.M., El-Faham, A. et al. (1998) Use of onium salt-based coupling reagents in peptide synthesis. J. Org. Chem. 63, 9678–9683.
    • (1998) J. Org. Chem. , vol.63 , pp. 9678-9683
    • Albericio, F.1    Bofill, J.M.2    El-Faham, A.3
  • 34
    • 0014772602 scopus 로고
    • Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides
    • Kaiser, E., Colescott, R.L., Bossinger, C.D. et al. (1970) Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 34, 595–598.
    • (1970) Anal. Biochem. , vol.34 , pp. 595-598
    • Kaiser, E.1    Colescott, R.L.2    Bossinger, C.D.3
  • 36
    • 0035197046 scopus 로고    scopus 로고
    • Integration of mass spectrometry into early-phase discovery and development of central nervous system agents
    • Prokai, L., Zharikova, A., Janáky, T. et al. (2001) Integration of mass spectrometry into early-phase discovery and development of central nervous system agents. J. Mass Spectrom. 36, 1211–1219.
    • (2001) J. Mass Spectrom. , vol.36 , pp. 1211-1219
    • Prokai, L.1    Zharikova, A.2    Janáky, T.3
  • 37
    • 0037047248 scopus 로고    scopus 로고
    • Immobilized artificial membrane chromatography coupled with atmospheric pressure ionization mass spectrometry
    • Braddy, A.C., Janaky, T., and Prokai, L. (2002) Immobilized artificial membrane chromatography coupled with atmospheric pressure ionization mass spectrometry. J. Chromatogr. A 966, 81–87.
    • (2002) J. Chromatogr. A , vol.966 , pp. 81-87
    • Braddy, A.C.1    Janaky, T.2    Prokai, L.3
  • 38
    • 85138996718 scopus 로고    scopus 로고
    • ht t p: //www. r egi s t ech. com/I nf oPages / IamInfo/IamCareAndUse.html
    • ht t p: //www. r egi s t ech. com/I nf oPages / IamInfo/IamCareAndUse.html
  • 39
    • 0029330768 scopus 로고
    • Detection of secondary amine on solid phase
    • Vojkovsky, T. (1995) Detection of secondary amine on solid phase. Pept. Res. 8, 236–237.
    • (1995) Pept. Res. , vol.8 , pp. 236-237
    • Vojkovsky, T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.