Synthesis and biological activity of nociceptin/orphanin FQ(1-13)NH2 analogues modified in 9 and/or 13 position

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 15, 2006, Pages 4071-4074

  Naydenova, Emilia D ^a   Zhivkova, Vanya I ^a   Zamfirova, Rositza N ^b   Vezenkov, Lubomir T ^a   Dobrinova, Yordanka G ^b   Mateeva, Polina I ^b  

^a UNIVERSITY OF CHEMICAL TECHNOLOGY AND METALLURGY   (Bulgaria)

^b INSTITUTE OF PHYSIOLOGY   (Bulgaria)

Author keywords

Nociceptin analogues; Nociceptin orphanin FQ; NOP; Opioid peptides; Rat vas deferens; SPPS

Indexed keywords

4 DIMETHYLAMINOAZOBENZENE; BUTYRIC ACID; DIAMINOBUTANOIC ACID; DIAMINOPROPANOIC ACID; LYSINE; NALOXONE; NOCICEPTIN DERIVATIVE; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; NONHUMAN; RAT; SUBSTITUTION REACTION; VAS DEFERENS;

OPIOID PEPTIDES; PEPTIDE FRAGMENTS; RECEPTORS, OPIOID;

EID: 33745125996     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.04.086     Document Type: Article

References (15)

1. Meunier J.C., Mollereau C., Toll L., Suaudeau C., Moisand C., Alvinerie P., Butour J.-L., Guillemot J.-C., Ferrara P., Monsarrat B., Mazarguil H., Vassart G., Parmentier M., and Costentin J. Nature 377 (1995) 532
2. Reinscheid R.K., Nothacker H.P., Bourson A., Ardati A., Henningsen R.A., Bunzow J.R., Grandy D.K., Langen H., Monsma F.J., and Civelli O. Science 270 (1995) 792
3. Meunier J.C. Eur. J. Pharmacol. 340 (1997) 1
4. Calo' G., Guerrini R., Rizzi A., Salvadori S., and Regoli D. Br. J. Pharmacol. 129 (2000) 1261
5. Vlaskovska M., and Kasakov L. Biomed. Rev. 11 (2000) 1
6. Bocheva A., Pajpanova T., and Golovinsky E. Methods Find. Exp. Clin. Pharmacol. 21 (1999) 591
7. Guerrini R., Calo G., Rizzi A., Bigoni R., Bianchi C., Salvadori S., and Regoli D. J. Med. Chem. 40 (1997) 1789
8. Rizzi D., Rizzi A., Bigoni R., Camarda V., Marzola G., Guerrini R., De Risi C., Regoli D., and Calo G. J. Pharmacol. Exp. Ther. 300 (2002) 357
9. Varani K., Rizzi A., Calo G., Bigoni R., Toth G., Guerrini R., Gessi S., Salvadori S., Borea P.A., and Regoli D. Naunyn-Schmiedeberg's Arch. Pharmacol. 360 (1999) 270
10. Guerrini R., Carra' G., Calo' G., Trapella C., Marzola E., Rizzi D., Regoli D., and Salvadori S. J. Pept. Res. 63 (2004) 477
11. tBu)-OH. All coupling reactions were performed, using for amino acid/TBTU/HOBt/DIEA/resin a molar ratio of 3/2.9/3/6/1. The Fmoc-group was deprotected by a 20% piperidine solution in dimethylformamide. The coupling and deprotection reactions were checked by the Kaiser test. The cleavage of the synthesized peptide from the resin was done, using a mixture of 95 % trifluoroacetic acid (TFA), 2.5 % triisopropylsilan (TIS) and 2.5 % water. The protected amino acids were purchased from IrisBiotech (Germany). All other reagents and solvents were analytical or HPLC grade and were bought from Merck (Germany).
12. +).
13. 2 as a unit. All experiments on isolated smooth muscles have been performed according to the rules of the Ethics Committee of the Institute of Physiology, Bulgarian Academy of Sciences (registration FWA 00003059 by the US Department of Health and Human Services).
14. Rizzi D., Bigoni R., Rizzi A., Jenck F., Wichmann J., and Guerrini R. Naunyn-Schmiedeberg's Arch. Pharmacol. 363 (2001) 551
15. Chen L.X., Wang Z.Z., Wu H., Fang Q., Chen Y., and Wang R. Neurosci. Lett. 331 (2002) 95