Improvement of enzymatic stability and intestinal permeability of deuterohemin-peptide conjugates by specific multi-site N-methylation

Amino Acids

Volumn 43, Issue 6, 2012, Pages 2431-2441

  Dong, Qing Guang ^a   Zhang, Yong ^a   Wang, Meng Shu ^a   Feng, Jiao ^a   Zhang, Hai Hong ^a   Wu, Yong Ge ^a   Gu, Tie Jun ^a   Yu, Xiang Hui ^a   Jiang, Chun Lai ^a   Chen, Yan ^a   Li, Wei ^a   Kong, Wei ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

DhHP 6; Enzymatic stability; N methylated peptide; Permeability; ROS

Indexed keywords

DEUTEROHEMIN ALANYLHISTIDINYLTHREONYLVALYLGLUTAMYLLYSINE AMIDE; HYDROGEN PEROXIDE; PEROXIDASE; SCAVENGER; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CELL MEMBRANE PERMEABILITY; CELL STRAIN CACO 2; ENZYME STABILITY; GUT SAC; HOMOGENATE; INTESTINE; INTESTINE ABSORPTION; INTESTINE MUCOSA PERMEABILITY; METHYLATION; MONOLAYER CULTURE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN FUNCTION; SERUM; SYNTHESIS;

ANIMALS; CACO-2 CELLS; ENZYME STABILITY; HEMIN; HUMANS; INTESTINAL MUCOSA; METHYLATION; MICE; OLIGOPEPTIDES; PERMEABILITY; PEROXIDASE; SUBSTRATE SPECIFICITY;

EID: 84872675868     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-012-1322-y     Document Type: Article

References (39)

1. Artursson P, Karlsson J (1991) Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem Biophys Res Commun 175:880-885
2. Artursson P, Magnusson C (1990) Epithelial transport of drugs in cell culture. II: Effect of extracellular calcium concentration on the paracellular transport of drugs of different lipophilicities across monolayers of intestinal epithelial (Caco-2) cells. J Pharm Sci 79:595-600 (Pubitemid 20222724)
3. Barthe L, Woodley JF, Kenworthy S, Houin G (1998) An improved everted gut sac as a simple and accurate technique to measure paracellular transport across the small intestine. Eur J Drug Metab Pharmacokinet 23:313-323 (Pubitemid 28401125)
4. Barthe L, Woodley JF, Houin G (1999) Gastrointestinal absorption of drugs: methods and studies. Fundam Clin Pharmacol 13:154-168 (Pubitemid 32324243)
5. Berlett BS, Stadtman ER (1997) Protein oxidation in aging, disease, and oxidative stress. J Biol Chem 272:20313-20316 (Pubitemid 27355575)
6. Bernkop-Schnurch A, Walker G (2001) Multifunctional matrices for oral peptide delivery. Crit Rev Ther Drug Carrier Syst 18:459-501 (Pubitemid 33117496)
7. Biron E, Chatterjee J, Ovadia O, Langenegger D, Brueggen J, Hoyer D, Schmid HA, Jelinek R, Gilon C, Hoffman A, Kessler H (2008) Improving oral bioavailability of peptides by multiple N-methylation: somatostatin analogues. Angew Chem Int Ed Engl 47:2595-2599
8. Burton PS, Conradi RA, Hilgers AR, Ho NF (1993) Evidence for a polarized efflux system for peptides in the apical membrane of Caco-2 cells. Biochem Biophys Res Commun 190:760-766 (Pubitemid 23207830)
9. Chatterjee PK, Patel NS, Kvale EO, Brown PA, Stewart KN, Mota-Filipe H, Sharpe MA, Di Paola R, Cuzzocrea S, Thiemermann C (2004) EUK-134 reduces renal dysfunction and injury caused by oxidative and nitrosative stress of the kidney. Am J Nephrol 24:165-177 (Pubitemid 38456627)
10. Chatterjee J, Gilon C, Hoffman A, Kessler H (2008) N-methylation of peptides: A new perspective in medicinal chemistry. Acc Chem Res 41:1331-1342
11. Day BJ (2004) Catalytic antioxidants: A radical approach to new therapeutics. Drug Discov Today 9:557-566 (Pubitemid 38760179)
12. Gan LS, Niederer T, Eads C, Thakker D (1993) Evidence for predominantly paracellular transport of thyrotropin-releasing hormone across Caco-2 cell monolayers. Biochem Biophys Res Commun 197:771-777 (Pubitemid 24034636)
13. Gao JN, Hugger ED, Beck-Westermeyer MS, Borchardt RT (2001) Estimating intestinal mucosal permeation of compounds using Caco-2 cell monolayers. Curr Protoc Pharmacol Chapter 7:Unit 7.2
14. Gentilucci L, De MR, Cerisoli L (2010) Chemical modifications designed to improve peptide stability: incorporation of nonnatural amino acids, pseudo-peptide bonds, and cyclization. Curr Pharm Des 16:3185-3203
15. Grunwald J, Rejtar T, Sawant R, Wang Z, Torchilin VP (2009) TAT peptide and its conjugates: proteolytic stability. Bioconjug Chem 20:1531-1537
16. Guan SW, Li PF, Luo J, Li YY, Huang L, Wang G, Zhu LM, Fan HK, Li W, Wang LP (2010) A deuterohemin peptide extends lifespan and increases stress resistance in Caenorhabditis elegans. Free Radic Res 44:813-820
17. Hamman JH, Enslin GM, Kotze AF (2005) Oral delivery of peptide drugs: barriers and developments. BioDrugs 19:165-177 (Pubitemid 40994232)
18. Han HK, StewartBH, DohertyAM, CodyWL,AmidonGL(1998) In vitro stability and intestinal absorption characteristics of hexapeptide endothelin receptor antagonists. Life Sci 63:1599-1609 (Pubitemid 28483123)
19. Hess S, Ovadia O, Shalev DE, Senderovich H, Qadri B, Yehezkel T, Salitra Y, Sheynis T, Jelinek R, Gilon C, Hoffman A (2007) Effect of structural and conformation modifications, including backbone cyclization, of hydrophilic hexapeptides on their intestinal permeability and enzymatic stability. J Med Chem 50:6201-6211
20. Lee HJ (2002) Protein drug oral delivery: the recent progress. Arch Pharm Res 25:572-584 (Pubitemid 43104176)
21. Lennernas H (1998) Human intestinal permeability. J Pharm Sci 87:403-410 (Pubitemid 28175799)
22. Linde Y, Ovadia O, Safrai E, Xiang Z, Portillo FP, Shalev DE, Haskell-Luevano C, Hoffman A, Gilon C (2008) Structure-Activity relationship and metabolic stability studies of backbone cyclization and N-methylation of melanocortin peptides. Biopolymers 90:671-682
23. Lister-James J, Dean RT, Pearson DA, Wilson DM (2001) Novel somatostatin analogs. WO 01/44177 A2
24. Liu, YL (2003) Peptide mimics of peroxidase with anti-cataract activity. Dissertation, University of Jilin, pp 65-70
25. Liu YL, Guo LL, Roger R, Luo GM, Li W (2001) The method improvement of synthesis and purification of deuterohemin. Acta Sci Nat Univ Jilin, 91-92
26. Mahato RI, Narang AS, Thoma L, Miller DD (2003) Emerging trends in oral delivery of peptide and protein drugs. Crit Rev Ther Drug Carrier Syst 20:153-214 (Pubitemid 37237279)
27. Mandelman D, Schwarz FP, Li H, Poulos TL (1998) The role of quaternary interactions on the stability and activity of ascorbate peroxidase. Protein Sci 7:2089-2098 (Pubitemid 28495795)
28. Masini E, Cuzzocrea S, Mazzon E, Marzocca C, Mannaioni PF, Salvemini D (2002) Protective effects of M40403, a selective superoxide dismutase mimetic, in myocardial ischaemia and reperfusion injury in vivo. Br J Pharmacol 136:905-917 (Pubitemid 34836865)
29. Nakabeppu Y, Tsuchimoto D, Yamaguchi H, Sakumi K (2007) Oxidative damage in nucleic acids and Parkinson's disease. J Neurosci Res 85:919-934 (Pubitemid 46580334)
30. Nestor JJ Jr (2009) The medicinal chemistry of peptides. Curr Med Chem 16:4399-4418
31. Ovadia O, Greenberg S, Chatterjee J, Laufer B, Opperer F, Kessler H, Gilon C, Hoffman A (2011) The effect of multiple N-methylation on intestinal permeability of cyclic hexapeptides. Mol Pharm 8:479-487
32. Reed TT (2011) Lipid peroxidation and neurodegenerative disease. Free Radic Biol Med 51:1302-1319
33. Rice-Evans CA, Diplock AT (1993) Current status of antioxidant therapy. Free Radic Biol Med 15:77-96
34. Smith KR, Uyeminami DL, Kodavanti UP, Crapo JD, Chang L, Pinkerton KE (2002) Inhibition of tobacco smoke-induced lung inflammation by a catalytic antioxidant. Free Radic Biol Med 33:1106-1114
35. Takacs-Novak K, Avdeef A, Box KJ, Podanyi B, Szasz G (1994) Determination of protonation macro-And microconstants and octanol/water partition coefficient of the antiinflammatory drug niflumic acid. J Pharm Biomed Anal 12:1369-1377 (Pubitemid 24339388)
36. Wang JY, Zhu SG, Xu CF (2002) Biochemistry, 3rd edn. Higher education press, Beijing, pp 174, 402-405
37. Wang LP, Liu YL, Yang H, Li W (2004) Synthesis and anti-cataract activity of a novel peroxidase mimetics. Chem J Chin Univ 25:2171-2173
38. Watson CJ, Rowland M, Warhurs G (2001) Functional modeling of tight junctions in intestinal cell monolayers using polyethylene glycol oligomers. Am J Physiol Cell Physiol 281:C388-C397
39. Woodley JF (1994) Enzymatic barriers for GI peptide and protein delivery. Crit Rev Ther Drug Carrier Syst 11:61-95