References
Groner B. Ed.; Peptides as drugs, discovery and
development, 2009, Wiley-VCH, Weinheim.
Dunn BM. Peptide Chemistry and Drug Design. Wiley
& Sons, New York (2015).
Schiller PW. Satellite Symposium Papers 9th
International Biophysics CongressRole of the
conformational element in peptide-receptor
interactions. Biophys. Chem. (1988) 31: 63-9.
Hruby VJ and Gehrig CA. Recent developments in the
design of receptor specific opioid peptides. Med. Res.
Rev. (1989) 9: 343-401.
DiMaio J, Nguyen TMD, Lemieux C and Schiller PW.
Synthesis and pharmacological characterization in-vitro
of cyclic enkephalin analogs: effect of conformational
constraints on opiate receptor selectivity. J. Med.
(1)
(2)
(3)
(4)
(5)
Chem. (1982) 25: 1432-8.
Rónai AZ, Székely JI, Berzétei I, Miglécz E and
Bajusz S. Tetrapeptide-amide analogues of enkephalin:
The role of C-terminus in determining the character
of opioid activity. Biochem. Biophys. Res. Commun.
(1979) 91: 1239-49.
Kodama H, Uchida H, Yasunaga T, Kondo M, Costa
T and Shimohigashi Y. Effect of modification of
enkephalin C-terminal functions on affinity selection
of opioid receptors. J. Mol. Recognit. (1990) 3: 197-
203.
Vardanyan R, Kumirov VK, Nichol GS, Davis P,
Liktor-Busa E, Rankin D, Varga E, Vanderah T, Porreca
F, Lai J and Hruby VJ. Synthesis and biological
evaluation of new opioid agonist and neurokinin-1
antagonist bivalent ligands. Bioorg. Med. Chem.
(2011) 19: 6135-42.
Lee YS, Kulkarani V, Cowell SM, Ma S-w, Davis P,
Hanlon KE, Vanderah TW, Lai J, Porreca F, Vardanyan
R and Hruby VJ. Development of Potent μ and δ
Opioid Agonists with High Lipophilicity. J. Med.
Chem. (2011) 54: 382-6.
Kamimura S, Akutsu M and Nishikawa M. Formation
of Thebaine in the Suspension Culture of Papaver
bracteatum. Agric. Biol. Chem. (1976) 40: 913-9.
Vincent PG and Engelke BF. High pressure liquid
chromatographic determination of the five major
alkaloids in Papaver somniferum L. and thebaine in
Papaver bracteatum Lindl. capsular tissue. J. AOAC.
Int. (1979) 62: 310-4.
Werner L, Wernerova M, Machara A, Endoma-Arias
MA, Duchek J, Adams DR, Cox DP and Hudlicky
T. Unexpected N-Demethylation of Oxymorphone
and Oxycodone N-Oxides Mediated by the Burgess
Reagent: Direct Synthesis of Naltrexone, Naloxone,
and Other Antagonists from Oxymorphone. Adv.
Synth. Catal. (2012) 354: 2706-12.
Boothby LA and Doering PL. Buprenorphine for the
treatment of opioid dependence. Am. J. Health Syst.
Pharm. (2007) 64: 266-72.
Machara A, Werner L, Endoma-Arias M.A, Cox DP
and Hudlicky T. Improved Synthesis of Buprenorphine
from Thebaine and/or Oripavine via PalladiumCatalyzed N-Demethylation/Acylation and/or
Concomitant O-Demethylation. Adv. Synth. Catal.
(2012) 354: 613-26.
Ohtani M. Basic pharmacology of buprenorphine. Eur.
J. Pain. Suppl. (2007) 1: 69-73.
Brown SM, Campbell SD, Crafford A, Regina KJ,
Holtzman MJ and Kharasch ED. P-Glycoprotein Is
a Major Determinant of Norbuprenorphine Brain
Exposure and Antinociception. J. Pharmacol. Exp.
Ther. (2012) 343: 53-61.
Rezaee Z, Arabanian A, Balalaie S, Ahmadiani A
and Nasoohi S. Semicarbazide Substitution Enhances
Enkephalins Resistance to Ace Induced Hydrolysis.
Int. J. Peptide Res. Therap. (2012) 18: 305-9.
Rezaee Z, Arabanian SA, Balalaie S, Ahmadiani A,
Khalaj L and Nasoohi S. Antinociceptive effect of
(6)
(7)
(8)
(9)
(10)
(11)
(12)
(13)
(14)
(15)
(16)
(17)
(18)
Synthesis of novel enkephalin analogues
1287
[Met5]enkephalin semicarbazide is not affected by
dipeptidyl carboxypeptidase-I. J. Pept. Sci. (2012)
18: 92-6.
Ramezanpour S, Nasoohi S, Balalaie S, Ardestani
J and Orooji A. In Amino Acids; Springer Wien
Sachsenplatz 4-6, PO BOX 89, A-1201 Wien, Austria,
(2015) 47: 1649-9.
Malakoutikhah M, Prades R, Teixidó M and Giralt
E. N-Methyl Phenylalanine-Rich Peptides as Highly
Versatile Blood−Brain Barrier Shuttles. J. Med. Chem.
(2010) 53: 2354-63.
Malakoutikhah M, Teixidó M and Giralt E. Toward an
Optimal Blood−Brain Barrier Shuttle by Synthesis and
Evaluation of Peptide Libraries. J. Med. Chem. (2008)
51: 4881-9.
Sewald N and Jakbuke H-D. Peptides: Chemistry and
Biology 2nd edition, Wiley-VCH Weinheim (2009).
Mergler M and Durieux JP. The Bachem Practice
of SPPS, BACHEM AG, Bubendorf, Switzerland
(2000).
(19)
(20)
(21)
(22)
(23)
Goodman M, Felix A, Moroder L and Toniolo C. Eds,
Synthesis of Peptides and Peptidomemtics, Thieme
Publisher, Stuttgart (2004).
Fan J, Brown SM. Tu Z and Kharasch ED. Chemical
and Enzyme-Assisted Syntheses of Norbuprenorphine3-β-D-Glucuronide. Bioconjugate Chem. (2011) 22:
752–58.
Lobbezoo MW, Soudijn W, I Van Wijngaarden W and
references cited therein. Opiate receptor interaction
of compounds derived from or structurally related to
fentanyl. J. Med. Chem. (1981) 24: 777-82.
Teixidó M, Zurita E, Malakoutikhah M, Tarragó T and
Giralt E. Diketopiperazines as a Tool for the Study of
Transport across the Blood−Brain Barrier (BBB) and
Their Potential Use as BBB-Shuttles. J. Am. Chem.
Soc. (2007) 129: 11802–13.
Malakoutikhah M, Teixidó M and Giralt E. Shuttle‐
Mediated Drug Delivery to the Brain Angew. Chem.
Int. Ed. (2011) 50: 7998-8014.
)