Stability of peptides and therapeutic success in cancer

Expert Opinion on Drug Metabolism and Toxicology

Volumn 7, Issue 7, 2011, Pages 793-802

  Pernot, Marlène ^a   Vanderesse, Régis ^a,c   Frochot, Céline ^b,c   Guillemin, François ^a,c   Barberi Heyob, Muriel ^a,c  

^a UNIVERSITÉ DE LORRAINE   (France)

^b UNIVERSITÉ DE LORRAINE   (France)

^c GDR CNRS 3049 Médicaments Photoactivables Photochimiothé rapie PHOTOMED   (France)

Author keywords

BBB; intestinal barrier; modified peptide; peptide; peptide stability; peptide metabolizing enzymes; structure activity relationship

Indexed keywords

AMINO ACID; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ATAZANAVIR; AZAPEPTIDE; AZATIDE; BESTATIN DERIVATIVE; BORTEZOMIB; CARBOXYPEPTIDASE C; CHEMOKINE RECEPTOR CXCR7; DIPEPTIDYL CARBOXYPEPTIDASE; DRUG METABOLIZING ENZYME; ENDOMORPHIN 1; GLUTAMYL AMINOPEPTIDASE; INDINAVIR; MEMBRANE METALLOENDOPEPTIDASE; MICROSOMAL AMINOPEPTIDASE; MORPHICEPTIN; NELFINAVIR; PEPTIDOMIMETIC AGENT; PEPTOID; PHOTOSENSITIZING AGENT; POLYPEPTIDE; PROSAPTIDE; PROTEINASE ACTIVATED RECEPTOR; PROTON; PSEUDOPEPTIDE; RITONAVIR; UNCLASSIFIED DRUG;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ALZHEIMER DISEASE; BIOLOGICAL ACTIVITY; BLOOD BRAIN BARRIER; CENTRAL NERVOUS SYSTEM DISEASE; CONJUGATION; DRUG DEGRADATION; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG METABOLISM; DRUG STABILITY; HUMAN; IN VIVO STUDY; INTESTINE CELL; MULTIPLE MYELOMA; NEOPLASM; NEUROMODULATION; NONHUMAN; PROTEIN CONFORMATION; PROTEIN EXPRESSION; PROTEIN STRUCTURE; PROTON TRANSPORT; REVIEW; RHEUMATOID ARTHRITIS; STRUCTURE ACTIVITY RELATION;

BIOLOGICAL AVAILABILITY; BLOOD-BRAIN BARRIER; DRUG STABILITY; HUMANS; INTESTINAL MUCOSA; MICROVILLI; NEOPLASMS; PEPTIDE HYDROLASES; PEPTIDES; PEPTIDOMIMETICS; TISSUE DISTRIBUTION;

EID: 79959255319     PISSN: 17425255     EISSN: 17447607     Source Type: Journal    
DOI: 10.1517/17425255.2011.574126     Document Type: Review

References (44)

1. Venkatraman J, Shankaramma SC, Balaram P. Design of folded peptides. Chem Rev 2001;7:3131-52 (Pubitemid 35377814)
2. Schneider R, Tirand L, Frochot C, et al. Recent improvements in the use of synthetic peptides for a selective photodynamic therapy. Anticancer Agents Med Chem 2006;6:469-88 (Pubitemid 44377781)
3. Adessi C, Soto C. Converting a peptide into a drug: strategies to improve stability and bioavailability. Curr Med Chem 2002;9:963-78 (Pubitemid 34498572)
4. Mc Donald J, Barrette A. Mammalian proteases: a glossary and bibliography. 1. Endopeptidases. Academic Press, London; 1980
5. Mc Donald J, Barrette A. Mammalian proteases: a glossary and bibliography. 2. Exopeptidases. Academic Press, London; 1986
6. Brigger I, Morizet J, Aubert G, et al. Poly(ethylene glycol)-coated hexadecylcyanoacrylate nanospheres display a combined effect for brain tumor targeting. J Pharmacol Exp Ther 2002;303:928-36 (Pubitemid 35424373)
7. Bellet-Amalric E, Blaudez D, Desbat B, et al. Interaction of the third helix of Antennapedia homeodomain and a phospholipid monolayer, studied by ellipsometry and PM-IRRAS at the air-water interface. Biochim Biophys Acta 2000;1467:131-43 (Pubitemid 30621592)
8. Ziegler A, Blatter XL, Seelig A, Seelig J. Protein transduction domains of HIV-1 and SIV TAT interact with charged lipid vesicles. Binding mechanism and thermodynamic analysis. Biochemistry 2003;42:9185-94
9. Jarver P, Mager I, Langel U. In vivo biodistribution and efficacy of peptide mediated delivery. Trends Pharmacol Sci 2010;31:528-35
10. Brownlees J, Williams CH. Peptidases, peptides, and the mammalian blood - brain barrier. J Neurochem 1993;60:793-803
11. Gach K, do-Rego JC, Fichna J, et al. Synthesis and biological evaluation of novel peripherally active morphiceptin analogs. Peptides 2010;31:1617-24
12. Janecka A, Staniszewska R, Gach K, Fichna J. Enzymatic degradation of endomorphins. Peptides 2008;29:2066-73
13. Tiruppathi C, Miyamoto Y, Ganapathy V, Leibach FH. Genetic evidence for role of DPP IV in intestinal hydrolysis and assimilation of prolyl peptides. Am J Physiol 1993;265:G81-9
14. Augustijns PF, Borchardt RT. Transport and metabolism of delta sleep-inducing peptide in cultured human intestinal epithelial cell monolayers. Drug Metab Dispos 1995;23:1372-8 (Pubitemid 26007843)
15. Morita A, Chung YC, Freeman HJ, et al. Intestinal assimilation of a proline-containing tetrapeptide. Role of a brush border membrane postproline dipeptidyl aminopeptidase IV. J Clin Invest 1983;72:610-16 (Pubitemid 13051321)
16. Thwaites DT, Brown CD, Hirst BH, Simmons NL. Transepithelial glycylsarcosine transport in intestinal Caco-2 cells mediated by expression of H(+)-coupled carriers at both apical and basal membranes. J Biol Chem 1993;268:7640-2 (Pubitemid 23120329)
17. Inui K, Yamamoto M, Saito H. Transepithelial transport of oral cephalosporins by monolayers of intestinal epithelial cell line Caco-2: specific transport systems in apical and basolateral membranes. J Pharmacol Exp Ther 1992;261:195-201
18. Ganapathy V, Leibach FH. Role of pH gradient and membrane potential in dipeptide transport in intestinal and renal brush-border membrane vesicles from the rabbit. Studies with L-carnosine and glycyl-L-proline. J Biol Chem 1983;258:14189-92 (Pubitemid 14217939)
19. Tamura K, Lee CP, Smith PL, Borchardt RT. Effect of charge on oligopeptide transporter-mediated permeation of cyclic dipeptides across Caco-2 cell monolayers. Pharm Res 1996;13:1752-4 (Pubitemid 26426905)
20. Tirand L, Frochot C, Vanderesse R, et al. A peptide competing with VEGF165 binding on neuropilin-1 mediates targeting of a chlorin-type photosensitizer and potentiates its photodynamic activity in human endothelial cells. J Control Release 2006;111:153-64 (Pubitemid 43290004)
21. Tirand L, Thomas N, Dodeller M, et al. Metabolic profile of a peptide-conjugated chlorin-type photosensitizer targeting neuropilin-1: an in vivo and in vitro study. Drug Metab Dispos 2007;35:806-13 (Pubitemid 46641552)
22. Tournaire R, Demangel C, Derbin C, et al. Peptides blocking vascular endothelial growth factor (VEGF)-mediated angiogenesis polynucleotides encoding said peptides and methods of use thereof. WO0172829; 2001
23. Thomas N, Tirand L, Chatelut E, et al. Tissue distribution and pharmacokinetics of an ATWLPPR-conjugated chlorin-type photosensitizer targeting neuropilin-1 in glioma-bearing nude mice. Photochem Photobiol Sci 2008;7:433-41 (Pubitemid 351490307)
24. Sheet T, Banerjee R. Sulfate ion interaction with 'anion recognition' short peptide motif at the N-terminus of an isolated helix: a conformational landscape. J Struct Biol 2010;171:345-52
25. Onoue S, Misaka S, Ohmori Y, et al. Physicochemical and pharmacological characterization of novel vasoactive intestinal peptide derivatives with improved stability. Eur J Pharm Biopharm 2009;73:95-101
26. Perez DR, Damberger FF, Wuthrich K. Horse prion protein NMR structure and comparisons with related variants of the mouse prion protein. J Mol Biol 2010;400:121-8
27. Shaikh N, Russo L, Papaleo E, et al. C-type natriuretic peptide: Structural studies, fragment synthesis, and preliminary biological evaluation in human osteosarcoma cell lines. Biopolymers 2010;94:213-19
28. Nicole P, Lins L, Rouyer-Fessard C, et al. Identification of key residues for interaction of vasoactive intestinal peptide with human VPAC1 and VPAC2 receptors and development of a highly selective VPAC1 receptor agonist. Alanine scanning and molecular modeling of the peptide. J Biol Chem 2000;275:24003-12 (Pubitemid 30624691)
29. Igarashi H, Ito T, Hou W, et al. Elucidation of vasoactive intestinal peptide pharmacophore for VPAC(1) receptors in human, rat, and guinea pig. J Pharmacol Exp Ther 2002;301:37-50
30. Adessi C, Frossard MJ, Boissard C, et al. Pharmacological profiles of peptide drug candidates for the treatment of Alzheimer's disease. J Biol Chem 2003;278:13905-11 (Pubitemid 36799931)
31. Lengauer T, Rarey M. Computational methods for biomolecular docking. Curr Opin Struct Biol 1996;6:402-6 (Pubitemid 26197442)
32. Walensky LD, Kung AL, Escher I, et al. Activation of apoptosis in vivo by a hydrocarbon-stapled BH3 helix. Science 2004;305:1466-70 (Pubitemid 39167667)
33. Bird GH, Madani N, Perry AF, et al. Hydrocarbon double-stapling remedies the proteolytic instability of a lengthy peptide therapeutic. Proc Natl Acad Sci USA 2010;107:14093-8
34. Guo Z, Mohanty U, Noehre J, et al. Probing the alpha-helical structural stability of stapled p53 peptides: molecular dynamics simulations and analysis. Chem Biol Drug Des 2010;75:348-59
35. Pitter K, Bernal F, Labelle J, Walensky LD. Dissection of the BCL-2 family signaling network with stabilized alpha-helices of BCL-2 domains. Methods Enzymol 2008;446:387-408
36. Stewart ML, Fire E, Keating AE, Walensky LD. The MCL-1 BH3 helix is an exclusive MCL-1 inhibitor and apoptosis sensitizer. Nat Chem Biol 2010;6:595-601
37. Iguchi S, Kawasaki K, Okamoto H, et al. Synthesis of some pseudo-peptide analogs of thiol proteinase inhibitors. Chem Pharm Bull (Tokyo) 1999;47:423-7 (Pubitemid 29166287)
38. Thomas N, Pernot M, Vanderesse R, et al. Photodynamic therapy targeting neuropilin-1: Interest of pseudopeptides with improved stability properties. Biochem Pharmacol 2010;80:226-35
39. Ripka AS, Rich DH. Peptidomimetic design. Curr Opin Chem Biol 1998;2:441-52 (Pubitemid 128645696)
40. Reubi JC. Peptide receptors as molecular targets for cancer diagnosis and therapy. Endocr Rev 2003;24:389-427 (Pubitemid 37056239)
41. Couleaud P, Bechet D, Vanderesse R, et al. Functionalized silica-based nanoparticles for photodynamic therapy. Nanomedicine Under Press
42. Berdowska I. Cysteine proteases as disease markers. Clin Chim Acta 2004;342:41-69 (Pubitemid 38352913)
43. van Kempen LC, de Visser KE, Coussens LM. Inflammation, proteases and cancer. Eur J Cancer 2006;42:728-34
44. Verhille M, Couleaud P, Vanderesse R, et al. Modulation of photosensitization processes for an improved targeted photodynamic therapy. Curr Med Chem 2010;17:3925-43