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Volumn 49, Issue 6, 2006, Pages 2016-2021

Analogues of neurohypophyseal hormones, oxytocin and arginine vasopressin, conformationally restricted in the N-terminal part of the molecule

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXYMETHYLCYSTEINE; ARGIPRESSIN DERIVATIVE; ARGIPRESSIN[1 (3 MERCAPTOCYCLOHEXANEACETIC ACID) 4 VALINE]; ARGIPRESSIN[1 (3 MERCAPTOPROPIONIC ACID) 4 VALINE]; ARGIPRESSIN[1 MERCAPTOCYCLOHEXANEACETIC ACID]; ARGIPRESSIN[3 MERCAPTOPROPIONIC ACID]; ARGIPRESSIN[4 VALINE]; NEUROHYPOPHYSIS HORMONE; OXYTOCIN; OXYTOCIN[1 MERCAPTOCYCLOHEXANEACETIC ACID]; OXYTOCIN[3 MERCAPTOPROPIONIC ACID]; UNCLASSIFIED DRUG;

EID: 33645381492     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm058038f     Document Type: Article
Times cited : (11)

References (37)
  • 1
    • 0023476138 scopus 로고
    • Neurohypophyseal hormone receptor systems in brain periphery
    • Jard, S.; Barberis, C.; Audigier, S.; Tribollet, E. Neurohypophyseal hormone receptor systems in brain periphery. Prog. Brain Res. 1987, 72, 173-187.
    • (1987) Prog. Brain Res. , vol.72 , pp. 173-187
    • Jard, S.1    Barberis, C.2    Audigier, S.3    Tribollet, E.4
  • 2
    • 0023795642 scopus 로고
    • Mechanisms of action of vasopressin antagonists
    • Jard, S. Mechanisms of action of vasopressin antagonists. Kidney Int. 1988, 34, 38-42.
    • (1988) Kidney Int. , vol.34 , pp. 38-42
    • Jard, S.1
  • 3
    • 0027532677 scopus 로고
    • Design, synthesis and some uses of receptor-specific agonists and antagonists of vasopressin and oxytocin
    • Manning, M.; Sawyer, W. H. Design, synthesis and some uses of receptor-specific agonists and antagonists of vasopressin and oxytocin. J. Receptor Res. 1993, 13, 195-214.
    • (1993) J. Receptor Res. , vol.13 , pp. 195-214
    • Manning, M.1    Sawyer, W.H.2
  • 4
    • 0026062086 scopus 로고
    • Pharmacology and clinical perspectives of vasopressin antagonists
    • Laszlo, F. A.; Laszlo, F., Jr.; De Wied, D. Pharmacology and clinical perspectives of vasopressin antagonists. Pharmacol. Rev. 1991, 43, 73-108.
    • (1991) Pharmacol. Rev. , vol.43 , pp. 73-108
    • Laszlo, F.A.1    Laszlo Jr., F.2    De Wied, D.3
  • 5
    • 0027248152 scopus 로고
    • Oxytocin antagonists in preterm labour and delivery
    • Melin, P. Oxytocin antagonists in preterm labour and delivery. Bailliere's Clin. Obstet. Gynaecol. 1993, 7, 577-600.
    • (1993) Bailliere's Clin. Obstet. Gynaecol. , vol.7 , pp. 577-600
    • Melin, P.1
  • 8
    • 0032578149 scopus 로고    scopus 로고
    • Substitution of the side-chain-constrained amino beta methyl-2,6-dimethyl-4-methoxytyrosine in position 2 of a bicyclic oxytocin analogue provides unique insights into the bioactive topography of oxytocin antagonists
    • Liao, S.; Shenderovich, M. D.; Zhigang, Z.; Maletinska, L.; Slaninová, J.; Hruby, V. J. Substitution of the side-chain-constrained amino beta methyl-2,6-dimethyl-4-methoxytyrosine in position 2 of a bicyclic oxytocin analogue provides unique insights into the bioactive topography of oxytocin antagonists. J. Am. Chem. Soc. 1998, 120, 7393-7394.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7393-7394
    • Liao, S.1    Shenderovich, M.D.2    Zhigang, Z.3    Maletinska, L.4    Slaninová, J.5    Hruby, V.J.6
  • 9
    • 0001161443 scopus 로고
    • Selective agonists and antagonists of vasopressin
    • Gash, D. M., Boer, G. J., Eds.; Plenum Press: New York
    • Manning, M.; Bańkowski, K.; Sawyer, W. H. Selective agonists and antagonists of vasopressin. In Vasopressin; Gash, D. M., Boer, G. J., Eds.; Plenum Press: New York, 1987; pp 335-368.
    • (1987) Vasopressin , pp. 335-368
    • Manning, M.1    Bańkowski, K.2    Sawyer, W.H.3
  • 11
    • 21844525636 scopus 로고
    • The 1- and 2-naphthylalanine analogues of oxytocin and vasopressin
    • Prochazka, Z.; Slaninová, J. The 1- and 2-naphthylalanine analogues of oxytocin and vasopressin. Collect. Czech. Chem. Commun. 1995, 60, 2170-2177.
    • (1995) Collect. Czech. Chem. Commun. , vol.60 , pp. 2170-2177
    • Prochazka, Z.1    Slaninová, J.2
  • 13
    • 0025370346 scopus 로고
    • Conformationally restricted peptides through short-range cyclizations
    • Toniolo C. Conformationally restricted peptides through short-range cyclizations. Int. J. Pept. Protein Res. 1990, 35, 287-300.
    • (1990) Int. J. Pept. Protein Res. , vol.35 , pp. 287-300
    • Toniolo, C.1
  • 14
    • 21844512808 scopus 로고
    • Conformational constraints emerging in the N,N′-ethylene- and N,N′-propylene-bridged dipeptide units
    • Czaplewski C.; Lammek B.; Ciarkowski J. Conformational constraints emerging in the N,N′-ethylene- and N,N′-propylene-bridged dipeptide units. Pol. J. Chem. 1994, 68, 2589-2598.
    • (1994) Pol. J. Chem. , vol.68 , pp. 2589-2598
    • Czaplewski, C.1    Lammek, B.2    Ciarkowski, J.3
  • 15
    • 85004878848 scopus 로고
    • N-methyl peptides: VII. Conformational perurbations induced by N-methylation of model dipeptides
    • Vituox B.; Aubry A.; Cung M. T.; Marraud M. N-methyl peptides: VII. Conformational perurbations induced by N-methylation of model dipeptides. Int. J. Pept. Protein Res. 1986, 27, 617-632.
    • (1986) Int. J. Pept. Protein Res. , vol.27 , pp. 617-632
    • Vituox, B.1    Aubry, A.2    Cung, M.T.3    Marraud, M.4
  • 16
    • 0031939551 scopus 로고    scopus 로고
    • Biologically active analogues of arginine vasopressin containing conformationally restricted dipeptide fragments
    • Lammek, B.; Czaja, M.; Derdowska, I.; Łempicka, E.; Sikora, P.; Szkróbka, W.; Trzeciak, H. I. Biologically active analogues of arginine vasopressin containing conformationally restricted dipeptide fragments. J. Pept. Res. 1998, 51, 149-154.
    • (1998) J. Pept. Res. , vol.51 , pp. 149-154
    • Lammek, B.1    Czaja, M.2    Derdowska, I.3    Łempicka, E.4    Sikora, P.5    Szkróbka, W.6    Trzeciak, H.I.7
  • 18
    • 0038684088 scopus 로고    scopus 로고
    • Influence of 1-aminocyclohexane-1-carboxylic acid in position 2 or 3 of AVP and its analogues on their pharmacological properties
    • Jastrzȩbska, B.; Derdowska, I.; Kowalczyk, W.; Machová, A.; Slaninová, J.; Lammek, B. Influence of 1-aminocyclohexane-1-carboxylic acid in position 2 or 3 of AVP and its analogues on their pharmacological properties. J. Pept. Res. 2003, 62, 70-71.
    • (2003) J. Pept. Res. , vol.62 , pp. 70-71
    • Jastrzȩbska, B.1    Derdowska, I.2    Kowalczyk, W.3    Machová, A.4    Slaninová, J.5    Lammek, B.6
  • 19
    • 8644242221 scopus 로고    scopus 로고
    • Highly potent 1-aminocyclohexane-1-carboxylic acid substituted V2 agonists of arginine vasopressin
    • Kowalczyk, W.; Prahl, A.; Derdowska, I.; Dawidowska, O.; Slaninová, J.; Lammek, B. Highly potent 1-aminocyclohexane-1-carboxylic acid substituted V2 agonists of arginine vasopressin. J. Med. Chem. 2004, 47, 6020-6024.
    • (2004) J. Med. Chem. , vol.47 , pp. 6020-6024
    • Kowalczyk, W.1    Prahl, A.2    Derdowska, I.3    Dawidowska, O.4    Slaninová, J.5    Lammek, B.6
  • 21
    • 11844275358 scopus 로고    scopus 로고
    • Influence of enantiomers of 1-naphthylalanine in position 2 of VAVP and dVAVP on their pharmacological properties
    • Derdowska, I.; Prahl, A.; Kowalczyk, W.; Janecki, M.; Melhem, S.; Trzeciak, HI.; Lammek, B. Influence of enantiomers of 1-naphthylalanine in position 2 of VAVP and dVAVP on their pharmacological properties. Eur. J. Med. Chem. 2005, 40, 63-68.
    • (2005) Eur. J. Med. Chem. , vol.40 , pp. 63-68
    • Derdowska, I.1    Prahl, A.2    Kowalczyk, W.3    Janecki, M.4    Melhem, S.5    Trzeciak, H.I.6    Lammek, B.7
  • 22
    • 4243767545 scopus 로고
    • S-Benzyl-α-hydroxymethylcysteine: Synthesis, resolution, absolute configuration
    • Leplawy, M. T.; Olma, A. S-Benzyl-α-hydroxymethylcysteine: synthesis, resolution, absolute configuration. Pol. J. Chem. 1979, 53, 353-355.
    • (1979) Pol. J. Chem. , vol.53 , pp. 353-355
    • Leplawy, M.T.1    Olma, A.2
  • 23
    • 0029945520 scopus 로고    scopus 로고
    • An efficient and high yield method for the N-tert-butyloxycarbonyl protection of sterically hindered amino acids
    • Khalil, E. M.; Subasinghe, N. L.; Johnson, R. L. An efficient and high yield method for the N-tert-butyloxycarbonyl protection of sterically hindered amino acids. Tetrahedron Lett. 1996, 37, 3441-3444.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3441-3444
    • Khalil, E.M.1    Subasinghe, N.L.2    Johnson, R.L.3
  • 24
    • 0000046837 scopus 로고
    • A highly potent analogue of oxytocin, desamino-oxytocin
    • Hope, D. B.; Murti, V. V. S.; Du Vigneaud, V. A highly potent analogue of oxytocin, desamino-oxytocin. J. Biol. Chem. 1962, 237, 1563.
    • (1962) J. Biol. Chem. , vol.237 , pp. 1563
    • Hope, D.B.1    Murti, V.V.S.2    Du Vigneaud, V.3
  • 25
    • 0000598726 scopus 로고
    • Synthesis of modified analogs of 1-(1-phenylmethylthiocyclohexane)-acetic acid
    • Rekowski, P.; Lammek, B. Synthesis of modified analogs of 1-(1-phenylmethylthiocyclohexane)-acetic acid. Pol. J. Chem. 1987, 61, 907-911.
    • (1987) Pol. J. Chem. , vol.61 , pp. 907-911
    • Rekowski, P.1    Lammek, B.2
  • 27
    • 0014432614 scopus 로고
    • Synthesis by the Merrifield method of a protected nonapeptide amide with the amino acid sequence of oxytocin
    • Manning, M. Synthesis by the Merrifield method of a protected nonapeptide amide with the amino acid sequence of oxytocin. J. Am. Chem. Soc. 1968, 90, 1348-1349.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 1348-1349
    • Manning, M.1
  • 28
    • 0023879271 scopus 로고
    • Synthesis of arginine-vasopressin modified in position 1 and 2 as antagonists of the vasopressor response to the parent hormone
    • Lammek, B.; Rekowski, P.; Kupryszewski, G.; Mellin, P.; Ragnarsson, U. Synthesis of arginine-vasopressin modified in position 1 and 2 as antagonists of the vasopressor response to the parent hormone. J. Med. Chem. 1988, 31, 603-606.
    • (1988) J. Med. Chem. , vol.31 , pp. 603-606
    • Lammek, B.1    Rekowski, P.2    Kupryszewski, G.3    Mellin, P.4    Ragnarsson, U.5
  • 29
    • 0014772602 scopus 로고
    • Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides
    • Kaiser, E.; Colescott, R. I.; Bossinger, C. D.; Cook, P. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970, 34, 595-598.
    • (1970) Anal. Biochem. , vol.34 , pp. 595-598
    • Kaiser, E.1    Colescott, R.I.2    Bossinger, C.D.3    Cook, P.4
  • 30
    • 0000795175 scopus 로고
    • A chloroanil color test for monitoring coupling completeness in solid-phase peptide synthesis
    • Gross, E., Meienhofer, J., Eds.; Pierce Chemical Company: Rockford, IL
    • Christensen, T. C. A chloroanil color test for monitoring coupling completeness in solid-phase peptide synthesis. In Peptides - Structure and Biological Function; Gross, E., Meienhofer, J., Eds.; Pierce Chemical Company: Rockford, IL, 1979; p 385.
    • (1979) Peptides - Structure and Biological Function , pp. 385
    • Christensen, T.C.1
  • 32
    • 84957417090 scopus 로고
    • A modification of the method of Dale and Laidlaw for standardization of posterior pituitary extract
    • Holton, P. A modification of the method of Dale and Laidlaw for standardization of posterior pituitary extract. Br. J. Pharmacol. 1948, 3, 328-334.
    • (1948) Br. J. Pharmacol. , vol.3 , pp. 328-334
    • Holton, P.1
  • 33
    • 0004124970 scopus 로고
    • Dose-response relations for some synthetic analogues of oxytocin, and the mode of action of oxytocin on the isolated uterus
    • Rudinger, J.; Krejči, I. Dose-response relations for some synthetic analogues of oxytocin, and the mode of action of oxytocin on the isolated uterus. Experientia 1962, 18, 585-588.
    • (1962) Experientia , vol.18 , pp. 585-588
    • Rudinger, J.1    Krejči, I.2
  • 34
    • 0001641316 scopus 로고
    • The quantitative assay of vasopressin
    • Dekanski, J. The quantitative assay of vasopressin. Br. J. Pharmacol. 1952, 7, 567-572.
    • (1952) Br. J. Pharmacol. , vol.7 , pp. 567-572
    • Dekanski, J.1
  • 36
    • 0016009677 scopus 로고
    • Antidiuretic action of 1-deamino-8-D-arginine vasopressin in unanesthetized rats
    • Vávra, I.; Machová, A.; Krejčí, I. Antidiuretic action of 1-deamino-8-D-arginine vasopressin in unanesthetized rats. J. Pharmacol. Exp. Ther. 1974, 188, 241-247.
    • (1974) J. Pharmacol. Exp. Ther. , vol.188 , pp. 241-247
    • Vávra, I.1    Machová, A.2    Krejčí, I.3
  • 37
    • 0002650676 scopus 로고
    • Fundamental biological evaluation
    • Jošt, K., Lebl, M., Brtník, F., Eds.; CRC Press Inc.: Boca Raton, FL
    • Slaninová, J. Fundamental Biological Evaluation. In Handbook of Neurohypophyseal Hormone Analogs; Jošt, K., Lebl, M., Brtník, F., Eds.; CRC Press Inc.: Boca Raton, FL, 1987; Vol. I, Part 2, pp 83-107.
    • (1987) Handbook of Neurohypophyseal Hormone Analogs , vol.1 , Issue.PART 2 , pp. 83-107
    • Slaninová, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.