PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
2006 | 53 | 1 |

Tytuł artykułu

The influence of modification at position 2 on the side-chain conformation in oxytocin analogs

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
The nonapeptide oxytocin (OT) is used in medicine to help begin and/or continue childbirth. Its analogs can be also used to control bleeding following fetus delivery. The main function of oxytocin is to stimulate contraction of uterus smooth muscle and the smooth muscle of mammary glands, thus regulating lactation. This paper describes theoretical simulations of the distribution of the torsional angles χ1 in the non-standard methylated phenylalanine residues of three oxytocin analogs: [(Phe)2o-Me]OT, [(Phe)2m-Me]OT, [(Phe)2p-Me]OT. The conformations of the oxytocin analogs were studied both in vacuum and in solution. We found some correlations between the biological activity of the considered peptides and the side-chain conformations of amino-acid residues 2 and 8.

Wydawca

-

Rocznik

Tom

53

Numer

1

Opis fizyczny

p.113-120,fig.,ref.

Twórcy

autor
  • University of Gdansk, Gdansk, Poland
autor

Bibliografia

  • Bankowski K, Manning M, Seto J, Haldar J, Sawyer WH (1980) Design and synthesis of potent in vivo antagonists of oxytocin. J Pept Protein Res 16: 382–391.
  • Barberis C, Mouillac B, Durroux T (1998) Structural bases of vasopressin/oxytocin receptor function. J Endocrinol 156: 223–229.
  • Bhargavi GR, Sheik SS, Velmurugan D, Sekar K (2003) Side-chain conformation angles of amino acids: effect of temperature factor cut-off. J Struct Biol 143: 181–184.
  • Bingham RC, Dewar MJS, Lo DH (1975) Ground states of molecules. XXV. MINDO/3. An improved version of the MINDO semiempirical SCF-MO method. J Am Chem Soc 97: 1285–1293.
  • Budesinsky M, Prochazka Z, Slaninova J (2005) Oxytocin and its analogs, methyl-substituted in ortho-, meta- or para- position of aromatic ring of phenylalanine in position 2: NMR study and biological activities. Protein Pept Lett 12: 343–347.
  • Burgess AW, McGuire RF, Momany FA, Scheraga HA (1975) Energy parameters in polypeptides. VII. Geometric parameters, partial atomic charges, non-bonded interactions, hydrogen bonded interactions, and intrinsic torsional potentials for the naturally occurring amino acids. J Phys Chem 79: 2361–2381.
  • Higby K, Suiter CR (1999) A risk-benefit assessment of therapies for premature labour. Drug Safety 21: 35–56.
  • Hruby VJ, Chan WY, Rockway TW, Hlavacek J, Ormberg J (1994) Design and synthesis of long-acting oxytocin anatagonists substituted in positions 2, 7, and 8. In Peptides: Design, Synthesis and Biological Activity (Basava C, Anantharamaiah GM, eds) vol 1, pp 198–208, Birkhauser Verlag, Boston.
  • Law D, Vigneaud VD (1960) Synthesis of 2-p-methoxyphenylalanine oxytocin (O-methyl-oxytocin) and some observations on its pharmacological behaviour. J Am Chem Soc 82: 4579–4581.
  • Manning M, Nawrocka E, Misicka A, Olma A, Klis WA, Seto J, Sawyer WH (1984) Potent and selective antagonists of the antidiuretic responses to arginine-vasopressin based on modifications of [1-(beta-mercaptobeta, beta-pentamethylenepropionic acid),2-D-isoleucine, 4-valine]arginine-vasopressin at position 4. J Med Chem 27: 423–429.
  • Manning M, Cheng LL, Stoev S, Bankowski K, Przybylski J, Klis WA, Sawyer WH, Wo NC, Chan WY (1995) An exploration of the effects of L- and D-tetrahydroisoquinoline-3-carboxylic acid substitutions at positions 2, 3 and 7 in cyclic and linear antagonists of vasopressin and oxytocin and at position 3 in arginine vasopressin. J Pept Sci 1: 66–79.
  • Marcus E, Keller DA, Shibata M, Ornstein RL, Rein R (1996) Comparing theoretical and experimental backbone-dependent sidechain conformational preferences for linear, branched, aromatic and polar residues. Chemical Physics 204: 157–171.
  • Nemethy G, Pottle MS, Scheraga HA (1983) Energy paramters in polypeptides. 9. Updating of geometrical parameters, non-bonding interactions and hydrogen bonding interactions for naturally occuring amino acids. J Phys Chem 87: 1883–1887.
  • Nemethy G, Gibson KD, Palmer KA, Yoon CN, Paterlini G, Zagari A, Rumsey S, Scheraga HA (1992) Improved geometrical parameters and nonbonded interactions to use in the ECEPP/3 algorithms, with applications to proline-containing peptides. J Phys Chem 96: 6472–6484.
  • Pearlman DA, Case DA, Caldwell JW, Ross WS, T. E. Cheatham III TE, DeBolt S, Ferguson D, Seibel G, Kollman P (1995) AMBER, a package of computer programs for applying molecular mechanics, normal mode analysis, molecular dynamics and free energy calculations to simulate the structural and energetic properties of molecules. Comp Phys Commun 91: 1–41.
  • Schaftenaar G, Noordik JH (2000) Molden: a pre- and postprocessing program for molecular and electronic structures. J Comput-Aided Mol Design 14: 123–134.
  • Slaninova J, Maletinska L, Vondrasek J, Zertova M, Prochazka J (2001) Magnesium and biological activity of oxytocin analogs modified on aromatic ring of amino acid in position 2. J Pept Sci 7: 413–424.
  • Toth GK, Bakos K, Penke B, Pavo I, Varga C, Torok G, Peter A, Fulop F (1999) Synthesis of oxytocin antagonists containing conformationally constrained amino acids in position 2. Bioorg Med Chem Lett 9: 667–672.
  • Urry DW, Ohnishi M, Walter R (1970) Secondary structure of the cyclic moiety of the peptide hormone oxytocin and its deamino analog. Proc Natl Acad Sci USA 66: 111–116.
  • Wood SP, Tickle IJ, Treharne AM, Pitts JE, Mascarenhas Y, Li JY, Husain J, Cooper S, Blundell TL, Hruby VJ, Buku A, Fischman AJ, Wyssbrod HR (1986) Crystal structure analysis of deamino-oxytocin: conformational flexibility and receptor binding. Science 232: 633–636.
  • Wyatt PG, Allen MJ, Chilcot J, Hickin G, Miller ND, Woollard PM (2001) Structure-activity relationship investigations of a potent and selective benzodiazepine oxytocin antagonist. Bioorg Med Chem Lett 11: 1301–1305.

Typ dokumentu

Bibliografia

Identyfikatory

Identyfikator YADDA

bwmeta1.element.agro-article-19477579-fa5d-4a01-8aa0-e50aaefb3a27
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.