메뉴 건너뛰기




Volumn 48, Issue 9, 2005, Pages 3379-3388

Design of benzophenone-containing photoactivatable linear vasopressin antagonists: Pharmacological and photoreactive properties

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPHENONE; IODINE 125; PHENYLACETYL DEXTRO BENZOYLPHENYLALANYLPHENYLALANYLGLUTAMINYLASPARAGINYLARGINYLPROLYLARGINYLTYROSINA MIDE; PHENYLACETYLBENZOYLPHENYLALANYLPHENYLALANYLGLUTAMINYLASPARAGINYLARGINYLPROL YLARGINYLTYROSINAMIDE; UNCLASSIFIED DRUG; VASOPRESSIN ANTAGONIST; VASOPRESSIN V1 RECEPTOR; VASOPRESSIN V1A RECEPTOR;

EID: 18244380327     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040871+     Document Type: Article
Times cited : (5)

References (41)
  • 1
    • 0000095906 scopus 로고
    • Vasopressin and oxytocin receptors: An overview
    • Elsevier: Amsterdam
    • Jard, S.; Elands, J.; Schmidt, A.; Barberis, C. Vasopressin and oxytocin receptors: an overview. Progress in Endocrinology; Elsevier: Amsterdam, 1988; pp 1183-1189.
    • (1988) Progress in Endocrinology , pp. 1183-1189
    • Jard, S.1    Elands, J.2    Schmidt, A.3    Barberis, C.4
  • 2
    • 0026604171 scopus 로고
    • Molecular cloning and expression of a rat V1a arginine vasopressin receptor
    • Morel, A.; O'Carroll, A. M.; Brownstein, M. J.; Lolait, S. J. Molecular cloning and expression of a rat V1a arginine vasopressin receptor. Nature 1992, 356, 523-526.
    • (1992) Nature , vol.356 , pp. 523-526
    • Morel, A.1    O'Carroll, A.M.2    Brownstein, M.J.3    Lolait, S.J.4
  • 3
    • 0027977854 scopus 로고
    • Cloning, functional expression and tissue distribution of human cDNA for the vascular-type vasopressin receptor
    • Hirasawa, A.; Shibata, K.; Kotosai, K.; Tsujimoto, G. Cloning, functional expression and tissue distribution of human cDNA for the vascular-type vasopressin receptor. Biochem. Biophys, Res. Commun. 1994, 203, 72-79.
    • (1994) Biochem. Biophys. Res. Commun. , vol.203 , pp. 72-79
    • Hirasawa, A.1    Shibata, K.2    Kotosai, K.3    Tsujimoto, G.4
  • 4
    • 0029094631 scopus 로고
    • Molecular cloning and sequencing of the gene encoding a sheep arginine vasopressin type 1a receptor
    • Hutchins, A. M.; Phillips, P. A.; Venter, D. J.; Burrell, L. M.; Johnston, C. I. Molecular cloning and sequencing of the gene encoding a sheep arginine vasopressin type 1a receptor. Biochim. Biophys. Acta 1995, 1263, 266-270.
    • (1995) Biochim. Biophys. Acta , vol.1263 , pp. 266-270
    • Hutchins, A.M.1    Phillips, P.A.2    Venter, D.J.3    Burrell, L.M.4    Johnston, C.I.5
  • 5
    • 0028017952 scopus 로고
    • Molecular cloning, sequencing, and functional expression of a cDNA encoding the human V1a vasopressin receptor
    • Thibonnier, M.; Auzan, C.; Madhun, Z.; Wilkins, P.; Berti-Mattera, L.; Clauser, E. Molecular cloning, sequencing, and functional expression of a cDNA encoding the human V1a vasopressin receptor. J. Biol. Chem. 1994, 269, 3304-3310.
    • (1994) J. Biol. Chem. , vol.269 , pp. 3304-3310
    • Thibonnier, M.1    Auzan, C.2    Madhun, Z.3    Wilkins, P.4    Berti-Mattera, L.5    Clauser, E.6
  • 7
    • 0031576219 scopus 로고    scopus 로고
    • Mapping peptide-binding domains of the human Via vasopressin receptor with a photoactivatable linear peptide antagonist
    • Phalipou, S.; Cotte, N.; Carnazzi, E.; Seyer, E.; Mahe, E.; Jard, S.; Barberis, C.; Mouillac, B. Mapping peptide-binding domains of the human Via vasopressin receptor with a photoactivatable linear peptide antagonist. J. Biol. Chem. 1997, 272, 26536-26544.
    • (1997) J. Biol. Chem. , vol.272 , pp. 26536-26544
    • Phalipou, S.1    Cotte, N.2    Carnazzi, E.3    Seyer, E.4    Mahe, E.5    Jard, S.6    Barberis, C.7    Mouillac, B.8
  • 8
    • 0033551670 scopus 로고    scopus 로고
    • Docking of linear peptide antagonists into the human V1a vasopressin receptor. Identification of binding domains by photoaffinity labeling
    • Phalipou, S.; Seyer, R.; Cotte, N.; Breton, C.; Barberis, C.; Hibert, M.; Mouillac, B. Docking of linear peptide antagonists into the human V1a vasopressin receptor. Identification of binding domains by photoaffinity labeling. J. Biol. Chem. 1999, 274, 23316-23327.
    • (1999) J. Biol. Chem. , vol.274 , pp. 23316-23327
    • Phalipou, S.1    Seyer, R.2    Cotte, N.3    Breton, C.4    Barberis, C.5    Hibert, M.6    Mouillac, B.7
  • 9
    • 0028305250 scopus 로고
    • A new series of photoactivatable and iodinatable linear vasopressin antagonists
    • Carnazzi, E.; Aumelas, A.; Barberis, C.; Guillon, G.; Seyer, R. A new series of photoactivatable and iodinatable linear vasopressin antagonists. J. Med. Chem. 1994, 37, 1841-1849.
    • (1994) J. Med. Chem. , vol.37 , pp. 1841-1849
    • Carnazzi, E.1    Aumelas, A.2    Barberis, C.3    Guillon, G.4    Seyer, R.5
  • 10
    • 0030835940 scopus 로고    scopus 로고
    • Efficient photoaffinity labeling of the rat V1a vasopressin receptor using a linear azidopeptidic antagonist
    • Carnazzi, E.; Aumelas, A.; Phalipou, S.; Mouillac, B.; Guillon, G.; Barberis, C.; Seyer, R. Efficient photoaffinity labeling of the rat V1a vasopressin receptor using a linear azidopeptidic antagonist. Eur. J. Biochem. 1997, 247, 906-913.
    • (1997) Eur. J. Biochem. , vol.247 , pp. 906-913
    • Carnazzi, E.1    Aumelas, A.2    Phalipou, S.3    Mouillac, B.4    Guillon, G.5    Barberis, C.6    Seyer, R.7
  • 12
    • 0033951038 scopus 로고    scopus 로고
    • Using photolabile ligands in drug discovery and development
    • Dorman, G.; Prestwich, G. D. Using photolabile ligands in drug discovery and development. Trends Biotechnol. 2000, 18, 64-77.
    • (2000) Trends Biotechnol. , vol.18 , pp. 64-77
    • Dorman, G.1    Prestwich, G.D.2
  • 13
    • 0030959062 scopus 로고    scopus 로고
    • Comparison of the photochemical behavior of four different photoactivatable probes
    • Weber, P. J.; Beck-Sickinger, A. G. Comparison of the photochemical behavior of four different photoactivatable probes. J. Pept. Res. 1997, 49, 375-383.
    • (1997) J. Pept. Res. , vol.49 , pp. 375-383
    • Weber, P.J.1    Beck-Sickinger, A.G.2
  • 14
    • 0028235205 scopus 로고
    • Benzophenone photophores in biochemistry
    • Dorman, G.; Prestwich, G. D. Benzophenone photophores in biochemistry. Biochemistry 1994, 33, 5661-5673.
    • (1994) Biochemistry , vol.33 , pp. 5661-5673
    • Dorman, G.1    Prestwich, G.D.2
  • 15
    • 0029859841 scopus 로고    scopus 로고
    • Identification of methionine as the site of covalent attachment of a p-benzoyl-phenylalanine-containing analogue of substance P on the substance P (NK-1) receptor
    • Kage, R.; Leeman, S. E.; Krause, J. E.; Costello, C. E.; Boyd, N. D. Identification of methionine as the site of covalent attachment of a p-benzoyl-phenylalanine-containing analogue of substance P on the substance P (NK-1) receptor. J. Biol. Chem. 1996, 271, 25797-25800.
    • (1996) J. Biol. Chem. , vol.271 , pp. 25797-25800
    • Kage, R.1    Leeman, S.E.2    Krause, J.E.3    Costello, C.E.4    Boyd, N.D.5
  • 16
    • 0037184607 scopus 로고    scopus 로고
    • Cgamma H2 of Met174 side chain is the site of covalent attachment of a substance P analogue photoactivable in position 5
    • Sachon, E.; Bolbach, G.; Chassaing, G.; Lavielle, S.; Sagan, S. Cgamma H2 of Met174 side chain is the site of covalent attachment of a substance P analogue photoactivable in position 5. J. Biol. Chem. 2002, 277, 50409-50414.
    • (2002) J. Biol. Chem. , vol.277 , pp. 50409-50414
    • Sachon, E.1    Bolbach, G.2    Chassaing, G.3    Lavielle, S.4    Sagan, S.5
  • 17
    • 0033305385 scopus 로고    scopus 로고
    • Direct identification of two contact sites for parathyroid hormone (PTH) in the novel PTH-2 receptor using photoaffinity cross-linking
    • Behar, V.; Bisello, A.; Rosenblatt, M.; Chorev, M. Direct identification of two contact sites for parathyroid hormone (PTH) in the novel PTH-2 receptor using photoaffinity cross-linking. Endocrinology 1999, 140, 4251-4261.
    • (1999) Endocrinology , vol.140 , pp. 4251-4261
    • Behar, V.1    Bisello, A.2    Rosenblatt, M.3    Chorev, M.4
  • 19
    • 0030970266 scopus 로고    scopus 로고
    • p-(4-hydroxybenzoyl)phenylalanine: A photoreactive amino acid analogue amenable to radioiodination for elucidation of peptide-protein interaction. Application to substance P receptor
    • Wilson, C. J.; Husain, S. S.; Stimson, E. R.; Dangott, L. J.; Miller, K. W.; Maggio, J. E. p-(4-Hydroxybenzoyl)phenylalanine: a photoreactive amino acid analogue amenable to radioiodination for elucidation of peptide-protein interaction. Application to substance P receptor. Biochemistry 1997, 36, 4542-4551.
    • (1997) Biochemistry , vol.36 , pp. 4542-4551
    • Wilson, C.J.1    Husain, S.S.2    Stimson, E.R.3    Dangott, L.J.4    Miller, K.W.5    Maggio, J.E.6
  • 20
    • 0028955412 scopus 로고
    • Synthesis of highly tritiated 4-benzoyl-L-phenylalanine, a photoactivatable amino acid
    • Dorman, G.; Olszewski, J. D.; Prestwich, G. D. Synthesis of highly tritiated 4-benzoyl-L-phenylalanine, a photoactivatable amino acid. J. Org. Chem. 1995, 60, 2292-2297.
    • (1995) J. Org. Chem. , vol.60 , pp. 2292-2297
    • Dorman, G.1    Olszewski, J.D.2    Prestwich, G.D.3
  • 21
    • 0035974702 scopus 로고    scopus 로고
    • Design, synthesis and pharmacological characterization of a potent radioiodinated and photoactivatable peptidic oxytocin antagonist
    • Carnazzi, E.; Aumelas, A.; Mouillac, B.; Breton, C.; Guillou, L.; Barberis, C.; Seyer, R. Design, synthesis and pharmacological characterization of a potent radioiodinated and photoactivatable peptidic oxytocin antagonist. J. Med. Chem. 2001, 44, 3022-3030.
    • (2001) J. Med. Chem. , vol.44 , pp. 3022-3030
    • Carnazzi, E.1    Aumelas, A.2    Mouillac, B.3    Breton, C.4    Guillou, L.5    Barberis, C.6    Seyer, R.7
  • 23
    • 0019830566 scopus 로고
    • Synthetic antagonists of in vivo antidiuretic and vasopressor responses to arginine-vasopressin
    • Manning, M.; Lammek, B.; Kolodziejczyk, A. M.; Seto, J.; Sawyer, W. H. Synthetic antagonists of in vivo antidiuretic and vasopressor responses to arginine-vasopressin. J. Med. Chem. 1981, 24, 701-706.
    • (1981) J. Med. Chem. , vol.24 , pp. 701-706
    • Manning, M.1    Lammek, B.2    Kolodziejczyk, A.M.3    Seto, J.4    Sawyer, W.H.5
  • 24
    • 0019178014 scopus 로고
    • N-acetyl-[2-(O-methyl)tyrosine]-arginine-vasopressin, an interesting antagonist of the vasopressor response to vasopressin
    • Jones, D. A., Jr.; Sawyer, W. H. N-Acetyl-[2-(O-methyl)tyrosine]- arginine-vasopressin, an interesting antagonist of the vasopressor response to vasopressin. J. Med. Chem. 1980, 23, 696-698.
    • (1980) J. Med. Chem. , vol.23 , pp. 696-698
    • Jones Jr., D.A.1    Sawyer, W.H.2
  • 25
    • 51849181148 scopus 로고
    • Determination of D-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene
    • Marfey, P. Determination of D-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene. Carlsberg Res. Commun. 1984, 49, 591-596.
    • (1984) Carlsberg Res. Commun. , vol.49 , pp. 591-596
    • Marfey, P.1
  • 26
    • 0035920099 scopus 로고    scopus 로고
    • Direct identification of human oxytocin receptor-binding domains using a photoactivatable cyclic peptide antagonist: Comparison with the human V1a vasopressin receptor
    • Breton, C.; Chellil, H.; Kabbaj-Benmansour, M.; Carnazzi, E.; Seyer, R.; Phalipou, S.; Morin, D.; Durroux, T.; Zingg, H.; Barberis, C.; Mouillac, B. Direct identification of human oxytocin receptor-binding domains using a photoactivatable cyclic peptide antagonist: comparison with the human V1a vasopressin receptor. J. Biol. Chem. 2001, 276, 26931-26941.
    • (2001) J. Biol. Chem. , vol.276 , pp. 26931-26941
    • Breton, C.1    Chellil, H.2    Kabbaj-Benmansour, M.3    Carnazzi, E.4    Seyer, R.5    Phalipou, S.6    Morin, D.7    Durroux, T.8    Zingg, H.9    Barberis, C.10    Mouillac, B.11
  • 27
    • 0030964782 scopus 로고    scopus 로고
    • Identification of angiotensin II-binding domains in the rat AT2 receptor with photolabile angiotensin analogs
    • Servant, G.; Laporte, S. A.; Leduc, R.; Escher, E.; Guillemette, G. Identification of angiotensin II-binding domains in the rat AT2 receptor with photolabile angiotensin analogs. J. Biol. Chem. 1997, 272, 8653-8659.
    • (1997) J. Biol. Chem. , vol.272 , pp. 8653-8659
    • Servant, G.1    Laporte, S.A.2    Leduc, R.3    Escher, E.4    Guillemette, G.5
  • 28
    • 0028861701 scopus 로고
    • Mapping peptide-binding domains of the substance P (NK-1) receptor from P388D1 cells with photolabile agonists
    • Li, Y. M.; Marnerakis, M.; Stimson, E. R.; Maggio, J. E. Mapping peptide-binding domains of the substance P (NK-1) receptor from P388D1 cells with photolabile agonists. J. Biol. Chem. 1995, 270, 1213-1220.
    • (1995) J. Biol. Chem. , vol.270 , pp. 1213-1220
    • Li, Y.M.1    Marnerakis, M.2    Stimson, E.R.3    Maggio, J.E.4
  • 29
    • 0027418570 scopus 로고
    • Photoaffinity labeling of central cholecystokinin receptors with high efficiency
    • Thiele, C.; Fahrenholz, F. Photoaffinity labeling of central cholecystokinin receptors with high efficiency. Biochemistry 1993, 32, 2741-2746.
    • (1993) Biochemistry , vol.32 , pp. 2741-2746
    • Thiele, C.1    Fahrenholz, F.2
  • 31
    • 0027340375 scopus 로고
    • Sar1-p-benzoylphenylalanine-angiotensin, a new photoaffinity probe for selective labeling of the type 2 angiotensin receptor
    • Bosse, R.; Servant, G.; Zhou, L. M.; Boulay, G.; Guillemette, G.; Escher, E. Sar1-p-benzoylphenylalanine-angiotensin, a new photoaffinity probe for selective labeling of the type 2 angiotensin receptor. Regul. Pept. 1993, 44, 215-223.
    • (1993) Regul. Pept. , vol.44 , pp. 215-223
    • Bosse, R.1    Servant, G.2    Zhou, L.M.3    Boulay, G.4    Guillemette, G.5    Escher, E.6
  • 32
    • 0020026845 scopus 로고
    • Design of more potent antagonists of the antidiuretic responses to arginine-vasopressin
    • Manning, M.; Olma, A.; Klis, W. A.; Kolodziejczyk, A. M.; Seto, J.; Sawyer, W. H. Design of more potent antagonists of the antidiuretic responses to arginine-vasopressin. J. Med. Chem. 1982, 25, 45-50.
    • (1982) J. Med. Chem. , vol.25 , pp. 45-50
    • Manning, M.1    Olma, A.2    Klis, W.A.3    Kolodziejczyk, A.M.4    Seto, J.5    Sawyer, W.H.6
  • 33
    • 0018358910 scopus 로고
    • Active site studies of neurohypophyseal hormones. Comparison of oxytocin and arginine vasopressin analogues containing 2-D-tyrosine
    • Hruby, V. J.; Upson, D. A.; Yamamoto, D. M.; Smith, C. W.; Walter, R. Active site studies of neurohypophyseal hormones. Comparison of oxytocin and arginine vasopressin analogues containing 2-D-tyrosine. J. Am. Chem. Soc. 1979, 101, 2717.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 2717
    • Hruby, V.J.1    Upson, D.A.2    Yamamoto, D.M.3    Smith, C.W.4    Walter, R.5
  • 34
    • 0020084917 scopus 로고
    • Antagonists of vasopressor and antidiuretic responses to arginine vasopressin
    • Manning, M.; Sawyer, W. H. Antagonists of vasopressor and antidiuretic responses to arginine vasopressin. Ann. Intern. Med. 1982, 96, 520-522.
    • (1982) Ann. Intern. Med. , vol.96 , pp. 520-522
    • Manning, M.1    Sawyer, W.H.2
  • 35
    • 0022399532 scopus 로고
    • Synthesis and some pharmacological properties of 18 potent O-alkyltyrosine-substituted antagonists of the vasopressor responses to arginine-vasopressin
    • Manning, M.; Lammek, B.; Bankowski, K.; Seto, J.; Sawyer, W. H. Synthesis and some pharmacological properties of 18 potent O-alkyltyrosine-substituted antagonists of the vasopressor responses to arginine-vasopressin. J. Med. Chem. 1985, 28, 1485-1491.
    • (1985) J. Med. Chem. , vol.28 , pp. 1485-1491
    • Manning, M.1    Lammek, B.2    Bankowski, K.3    Seto, J.4    Sawyer, W.H.5
  • 37
    • 0029785689 scopus 로고    scopus 로고
    • Differential expression and butyrate response of human alkaline phosphatase genes are mediated by upstream DNA elements
    • Park, C.; Chamberlin, M. E.; Pan, C. J.; Chou, J. Y. Differential expression and butyrate response of human alkaline phosphatase genes are mediated by upstream DNA elements. Biochemistry 1996, 35, 9807-9814.
    • (1996) Biochemistry , vol.35 , pp. 9807-9814
    • Park, C.1    Chamberlin, M.E.2    Pan, C.J.3    Chou, J.Y.4
  • 38
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248-254.
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 39
    • 0019061918 scopus 로고
    • Ligand: A versatile computerized approach for characterization of ligand-binding systems
    • Munson, P. J.; Rodbard, D. Ligand: a versatile computerized approach for characterization of ligand-binding systems. Anal. Biochem. 1980, 107, 220-239.
    • (1980) Anal. Biochem. , vol.107 , pp. 220-239
    • Munson, P.J.1    Rodbard, D.2
  • 40
    • 0344149700 scopus 로고
    • Pharmacological characterization of two specific binding sites for neurohypophyseal hormones in hippocampal synaptic plasma membranes of the rat
    • Audigier, S.; Barberis, C. Pharmacological characterization of two specific binding sites for neurohypophyseal hormones in hippocampal synaptic plasma membranes of the rat. EMBO J. 1985, 4, 1407-1412.
    • (1985) EMBO J. , vol.4 , pp. 1407-1412
    • Audigier, S.1    Barberis, C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.