Skip to main content
Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1990 Jun;87(12):4836–4839. doi: 10.1073/pnas.87.12.4836

cDNAs encoding [D-Ala2]deltorphin precursors from skin of Phyllomedusa bicolor also contain genetic information for three dermorphin-related opioid peptides.

K Richter 1, R Egger 1, L Negri 1, R Corsi 1, C Severini 1, G Kreil 1
PMCID: PMC54213  PMID: 2352951

Abstract

We present the structure of four precursors for [D-Ala2]deltorphins I and II as deduced from cDNAs cloned from skin of the frog Phyllomedusa bicolor. These contain the genetic information for one copy of [D-Ala2]deltorphin II and zero, one, or three copies of [D-Ala2]deltorphin I. In each case, the D-alanine of the end product is encoded by a normal GCG codon for L-alanine. In addition, the existence of three peptides related to dermorphin was predicted from the amino acid sequence of the precursors. These peptides were synthesized with a D-alanine in position 2 and their pharmacological properties were tested. Two of them, [Lys7]dermorphin-OH and [Trp4,Asn7]dermorphin-OH, were found to have roughly the same affinity and selectivity for mu-type opioid receptors as dermorphin.

Full text

PDF
4836

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Amiche M., Sagan S., Mor A., Delfour A., Nicolas P. Dermenkephalin (Tyr-D-Met-Phe-His-Leu-Met-Asp-NH2): a potent and fully specific agonist for the delta opioid receptor. Mol Pharmacol. 1989 Jun;35(6):774–779. [PubMed] [Google Scholar]
  2. Bradbury A. F., Finnie M. D., Smyth D. G. Mechanism of C-terminal amide formation by pituitary enzymes. Nature. 1982 Aug 12;298(5875):686–688. doi: 10.1038/298686a0. [DOI] [PubMed] [Google Scholar]
  3. Erspamer V., Melchiorri P., Falconieri Erspamer G., Montecucchi P. C., de Castiglione R. Phyllomedusa skin: a huge factory and store-house of a variety of active peptides. Peptides. 1985;6 (Suppl 3):7–12. doi: 10.1016/0196-9781(85)90343-2. [DOI] [PubMed] [Google Scholar]
  4. Erspamer V., Melchiorri P., Falconieri-Erspamer G., Negri L., Corsi R., Severini C., Barra D., Simmaco M., Kreil G. Deltorphins: a family of naturally occurring peptides with high affinity and selectivity for delta opioid binding sites. Proc Natl Acad Sci U S A. 1989 Jul;86(13):5188–5192. doi: 10.1073/pnas.86.13.5188. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Gibson B. W., Poulter L., Williams D. H., Maggio J. E. Novel peptide fragments originating from PGLa and the caerulein and xenopsin precursors from Xenopus laevis. J Biol Chem. 1986 Apr 25;261(12):5341–5349. [PubMed] [Google Scholar]
  6. Gubler U., Hoffman B. J. A simple and very efficient method for generating cDNA libraries. Gene. 1983 Nov;25(2-3):263–269. doi: 10.1016/0378-1119(83)90230-5. [DOI] [PubMed] [Google Scholar]
  7. Kreil G., Barra D., Simmaco M., Erspamer V., Erspamer G. F., Negri L., Severini C., Corsi R., Melchiorri P. Deltorphin, a novel amphibian skin peptide with high selectivity and affinity for delta opioid receptors. Eur J Pharmacol. 1989 Mar 14;162(1):123–128. doi: 10.1016/0014-2999(89)90611-0. [DOI] [PubMed] [Google Scholar]
  8. Lazarus L. H., Wilson W. E., de Castiglione R., Guglietta A. Dermorphin gene sequence peptide with high affinity and selectivity for delta-opioid receptors. J Biol Chem. 1989 Feb 25;264(6):3047–3050. [PubMed] [Google Scholar]
  9. Maxam A. M., Gilbert W. Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol. 1980;65(1):499–560. doi: 10.1016/s0076-6879(80)65059-9. [DOI] [PubMed] [Google Scholar]
  10. Montecucchi P. C., de Castiglione R., Piani S., Gozzini L., Erspamer V. Amino acid composition and sequence of dermorphin, a novel opiate-like peptide from the skin of Phyllomedusa sauvagei. Int J Pept Protein Res. 1981 Mar;17(3):275–283. doi: 10.1111/j.1399-3011.1981.tb01993.x. [DOI] [PubMed] [Google Scholar]
  11. Mor A., Delfour A., Sagan S., Amiche M., Pradelles P., Rossier J., Nicolas P. Isolation of dermenkephalin from amphibian skin, a high-affinity delta-selective opioid heptapeptide containing a D-amino acid residue. FEBS Lett. 1989 Sep 25;255(2):269–274. doi: 10.1016/0014-5793(89)81104-4. [DOI] [PubMed] [Google Scholar]
  12. Richter K., Egger R., Kreil G. D-alanine in the frog skin peptide dermorphin is derived from L-alanine in the precursor. Science. 1987 Oct 9;238(4824):200–202. doi: 10.1126/science.3659910. [DOI] [PubMed] [Google Scholar]
  13. Richter K., Egger R., Kreil G. Sequence of preprocaerulein cDNAs cloned from skin of Xenopus laevis. A small family of precursors containing one, three, or four copies of the final product. J Biol Chem. 1986 Mar 15;261(8):3676–3680. [PubMed] [Google Scholar]
  14. Sagan S., Amiche M., Delfour A., Camus A., Mor A., Nicolas P. Differential contribution of C-terminal regions of dermorphin and dermenkephalin to opioid-sites selection and binding potency. Biochem Biophys Res Commun. 1989 Sep 15;163(2):726–732. doi: 10.1016/0006-291x(89)92283-3. [DOI] [PubMed] [Google Scholar]
  15. Sanger F., Coulson A. R., Barrell B. G., Smith A. J., Roe B. A. Cloning in single-stranded bacteriophage as an aid to rapid DNA sequencing. J Mol Biol. 1980 Oct 25;143(2):161–178. doi: 10.1016/0022-2836(80)90196-5. [DOI] [PubMed] [Google Scholar]
  16. Schwartz T. W. The processing of peptide precursors. 'Proline-directed arginyl cleavage' and other monobasic processing mechanisms. FEBS Lett. 1986 May 5;200(1):1–10. doi: 10.1016/0014-5793(86)80500-2. [DOI] [PubMed] [Google Scholar]
  17. Singer-Sam J., Simmer R. L., Keith D. H., Shively L., Teplitz M., Itakura K., Gartler S. M., Riggs A. D. Isolation of a cDNA clone for human X-linked 3-phosphoglycerate kinase by use of a mixture of synthetic oligodeoxyribonucleotides as a detection probe. Proc Natl Acad Sci U S A. 1983 Feb;80(3):802–806. doi: 10.1073/pnas.80.3.802. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Suchanek G., Kreil G., Hermodson M. A. Amino acid sequence of honeybee prepromelittin synthesized in vitro. Proc Natl Acad Sci U S A. 1978 Feb;75(2):701–704. doi: 10.1073/pnas.75.2.701. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Proceedings of the National Academy of Sciences of the United States of America are provided here courtesy of National Academy of Sciences

RESOURCES