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2001 | 48 | 4 | 1121-1124
Article title

DALDA analogues containing α-hydroxymethylamino acids.

Content
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Languages of publication
EN
Abstracts
EN
To evaluate the role of aromatic amino-acids residues, four analogues of the μ-selec-tive opioid peptide agonist DALDA (H-Tyr-D-Arg-Phe-Lys-NH2) containing the amphiphilic, α,α-disubstituted amino acid (R)- or (S)-α-hydroxymethyltyrosine (HmTyr) in position 1 and (R)- or (S)-α-hydroxymethylphenylalanine (HmPhe) in position 3 of the peptide sequence were synthesized. Only the [(R)-HmPhe3)]DALDA analogue displayed full agonistic activity in both the guinea pig ileum and the mouse vas deferens assays and turned out to be a δ receptor-selective opioid agonist.
Publisher

Year
Volume
48
Issue
4
Pages
1121-1124
Physical description
Dates
published
2001
received
2001-09-19
accepted
2001-11-6
Contributors
  • Institute of Organic Chemistry, Technical University of Łódź, Łódź, Poland
author
  • Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, Montreal, Quebec, Canada
  • Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, Montreal, Quebec, Canada
  • Institute of Organic Chemistry, Technical University of Łódź, Łódź, Poland
References
  • 1. Schiller, P.W., Weltrowska, G., Berezowska, I., Nguyen, T.M.-D., Wilkes, B.C., Lemieux, C. L. & Chung, N. N. (1999) Biopolymers (Peptide Science) 51, 411-425.
  • 2. Schiller, P.W. (1991) in Progress in Medicinal Chemistry (Ellis, G.P. & West, G.B., eds.) vol. 28, pp.301-340, Elsevier, Amsterdam.
  • 3. Sato, T., Sakurada, S., Sakurada, T., Furuta, S., Chaki, K., Kisara, K., Sasaki, Y. & Suzuki, K. (1987) J. Pharmacol. Exp. Ther.242, 654-659.
  • 4. Schiller, P.W., Nguyen, T.M.-D., Chung, N.N. & Lemieux, C.L. (1989) J. Med. Chem. 32, 698-703.
  • 5. Kamiński, Z.J., Leplawy, M.T. & Zabrocki, J. (1973) Synthesis 792-793.
  • 6. Kamiński, Z.J. & Leplawy, M.T. (1974) Synthesis 292-293.
  • 7. Wieczorek, W., Bukowska-Strzyżewska, M., Leplawy, M.T. & Olma, A. (1991) J. Crystallogr. Spectroscop. Res. 21, 209-215.
  • 8. Olma, A. (1996) Polish J. Chem. 70, 1442-1447.
  • 9. Olma, A. & Tourwé, D. (2000) Lett. Pept. Sci. 7, 93-96.
  • 10. Kaiser, E., Colescott, R.L., Bossinger, C.D. & Cook, P. (1970) Anal. Biochem. 34, 595-598.
  • 11. Schiller, P.W., Lipton, A., Horrobin, D.F. & Bodanszky, M. (1978) Biochem. Biophys. Res. Commun. 85, 1332-1338.
  • 12. DiMaio, J., Nguyen, T.M.-D., Lemiex, C. & Schiller, P.W. (1982) J. Med. Chem. 25, 1432-1438.
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.bwnjournal-article-abpv48i4p1121kz
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