Impact of amino acid replacements on in vitro permeation enhancement and cytotoxicity of the intestinal absorption promoter, melittin

International Journal of Pharmaceutics

Volumn 387, Issue 1-2, 2010, Pages 154-160

  Maher, Sam ^a   Devocelle, Marc ^b   Ryan, Sinéad ^a   McClean, Siobhán ^c   Brayden, David J ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b ROYAL COLLEGE OF SURGEONS IN IRELAND   (Ireland)

^c DUBLIN INSTITUTE OF TECHNOLOGY   (Ireland)

Author keywords

Absorption promotion; Chemical modification of peptides; Cytotoxicity; Melittin; Oral macromolecule delivery

Indexed keywords

FLUORESCEIN ISOTHIOCYANATE; GLYCYLISOLEUCYLGLYCYLALANYLVALYLALANYLLYSYLVALYLLEUCYLTHREONYLTHREONYLGLYCYLALANYLPROLYLALANYLLEUCYLISOLEUCYLSERYLTRYPTOPHYLISOLEUCYLLYSYLARGINYLLYSYLARGINYLGLUTAMINYLGLUTAMINE; GLYCYLISOLEUCYLGLYCYLALANYLVALYLALANYLLYSYLVALYLLEUCYLTHREONYLTHREONYLGLYCYLALANYLPROLYLGLYCYLLEUCYLPROLYLALANYLLEUCYLISOLEUCYLSERYLTRYPTOPHYLISOLEUCYLLYSYLARGINYLLYSYLARGINYLGLUTAMINYLGLUTAMINE; GLYCYLISOLEUCYLGLYCYLALANYLVALYLLEUCYLLYSYLVALYLLEUCYLTHREONYLTHREONYLGLYCYLLEUCYLPROLYL LEUCYLISOLEUCYLSERYLTRYPTOPHYLISOLEUCYLLYSYLARGINYLLYSYLGLUTAMINYLGLUTAMINE; GLYCYLISOLEUCYLGLYCYLALANYLVALYLLEUCYLLYSYLVALYLLEUCYLTHREONYLTHREONYLGLYCYLLEUCYLPROLYLALANYLLEUCYLISOLEUCYLSERYL ISOLEUCYLLYSYLARGINYLLYSYLARGINYLGLUTAMINYLGLUTAMINE; GLYCYLISOLEUCYLGLYCYLALANYLVALYLLEUCYLLYSYLVALYLLEUCYLTHREONYLTHREONYLGLYCYLLEUCYLPROLYLALANYLLEUCYLISOLEUCYLSERYLTRYPTOPHYLISOLEUCYLLYSYLARGINYLLYSYLGLUTAMINYLGLUTAMINE; LACTATE DEHYDROGENASE; MELITTIN; METHYLTHIAZOLYDIPHENYL TETRAZOLIUM BROMIDE; PEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; CELL STRAIN CACO 2; CELL VIABILITY; CHEMICAL MODIFICATION; CONTROLLED STUDY; CYTOTOXICITY TEST; DRUG PENETRATION; DRUG STRUCTURE; ERYTHROCYTE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROPHOBICITY; INTESTINE ABSORPTION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN PURIFICATION;

EID: 77649183652     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2009.12.022     Document Type: Article

References (43)

1. Amory J.K., et al. Oral administration of the GnRH antagonist acyline, in a GIPET((R))-enhanced tablet form, acutely suppresses serum testosterone in normal men: single-dose pharmacokinetics and pharmacodynamics. Cancer Chemother Pharmacol. 2009, 64(3):641-645.
2. Asthana N., Yadav S.P., Ghosh J.K. Dissection of antibacterial and toxic activity of melittin: a leucine zipper motif plays a crucial role in determining its hemolytic activity but not antibacterial activity. J. Biol. Chem. 2004, 279(53):55042-55050.
3. Blondelle S.E., Houghten R.A. Hemolytic and antimicrobial activities of the twenty-four individual omission analogues of melittin. Biochemistry 1991, 30(19):4671-4678.
4. Blondelle S.E., Houghten R.A. Design of model amphipathic peptides having potent antimicrobial activities. Biochemistry 1992, 31(50):12688-12694.
5. Carpino L.A., Han G.Y. 9-Fluorenylmethoxycarbonyl Amino-Protecting Group. J. Org. Chem. 1972, 37(22):3404-3409.
6. Dempsey C.E. The actions of melittin on membranes. Biochim. Biophys. Acta 1990, 1031(2):143-161.
7. Fisher P.J., et al. Calmodulin interacts with amphiphilic peptides composed of all D-amino acids. Nature 1994, 368(6472):651-653.
8. Gonzalez-Mariscal L., Hernandez S., Vega J. Inventions designed to enhance drug delivery across epithelial and endothelial cells through the paracellular pathway. Recent Pat. Drug Deliv. Formul. 2008, 2(2):145-176.
9. Gonzalez-Mariscal L., Nava P., Hernandez S. Critical role of tight junctions in drug delivery across epithelial and endothelial cell layers. J. Membr. Biol. 2005, 207(2):55-68.
10. Hubatsch I., Ragnarsson E.G., Artursson P. Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers. Nat. Protoc. 2007, 2(9):2111-2119.
11. Johnson P.H., Frank D., Costantino H.R. Discovery of tight junction modulators: significance for drug development and delivery. Drug Discov Today 2008, 13(5-6):261-267.
12. Kim S., Kim S.S., Lee B.J. Correlation between the activities of alpha-helical antimicrobial peptides and hydrophobicities represented as RP HPLC retention times. Peptides 2005, 26(11):2050-2056.
13. Kondoh M., Takahashi A., Fujii M., Yagi K., Watanabe Y. A novel strategy for a drug delivery system using a claudin modulator. Biol. Pharm. Bull. 2006, 29(9):1783-1789.
14. Kondoh M., Yagi K. Progress in absorption enhancers based on tight junction. Expert Opin. Drug Deliv. 2007, 4(3):275-286.
15. Kondoh M., Yoshida T., Kakutani H., Yagi K. Targeting tight junction proteins-significance for drug development. Drug Discov. Today 2008, 13(3-4):180-186.
16. Leonard T.W., Lynch J., McKenna M.J., Brayden D.J. Promoting absorption of drugs in humans using medium-chain fatty acid-based solid dosage forms: GIPET. Expert Opin. Drug Deliv. 2006, 3(5):685-692.
17. Liu P., Davis P., Liu H., Krishnan T.R. Evaluation of cytotoxicity and absorption enhancing effects of melittin - a novel absorption enhancer. Eur. J. Pharm. Biopharm. 1999, 48(1):85-87.
18. Maher S., Brayden D.J., Feighery L., McClean S. Cracking the junction: update on the progress of gastrointestinal absorption enhancement in the delivery of poorly absorbed drugs. Crit. Rev. Ther. Drug Carrier Syst. 2008, 25(2):117-168.
19. Maher S., Feighery L., Brayden D.J., McClean S. Melittin as a permeability enhancer II: in vitro investigations in human mucus secreting intestinal monolayers and rat colonic mucosae. Pharm. Res. 2007, 24(7):1346-1356.
20. Maher S., Feighery L., Brayden D.J., McClean S. Melittin as an epithelial permeability enhancer I: investigation of its mechanism of action in Caco-2 monolayers. Pharm. Res. 2007, 24(7):1336-1345.
21. Maher S. Evaluation of intestinal absorption enhancement and local mucosal toxicity of two promoters. I. Studies in isolated rat and human colonic mucosae. Eur.J. Pharm. Sci. 2009, 38:291-300.
22. Maher S., Leonard M., Jette J., Brayden D.J. Safety and efficacy of sodium caprate in promoting oral drug absorption: from in vitro to the clinic. Adv. Drug Deliv. Rev. 2009, 61:1427-1449.
23. Maher S., McClean S. Investigation of the cytotoxicity of eukaryotic and prokaryotic antimicrobial peptides in intestinal epithelial cells in vitro. Biochem. Pharmacol. 2006, 71(9):1289-1298.
24. Maher S., McClean S. Melittin exhibits necrotic cytotoxicity in gastrointestinal cells which is attenuated by cholesterol. Biochem. Pharmacol. 2008, 75(5):1104-1114.
25. Maher S., Wang X., Bzik V., McClean S., Brayden D.J. Evaluation of intestinal absorption and mucosal toxicity using two promoters. II. Rat instillation and perfusion studies. Eur. J. Pharm. Sci. 2009, 38:301-311.
26. Merrifield B. Solid phase synthesis. Science 1986, 232(4748):341-347.
27. Motlekar N.A., Srivenugopal K.S., Wachtel M.S., Youan B.B. Oral delivery of low-molecular-weight heparin using sodium caprate as absorption enhancer reaches therapeutic levels. J. Drug Target 2005, 13(10):573-583.
28. Muranishi S. Absorption enhancers. Crit. Rev. Ther. Drug Carrier Syst. 1990, 7(1):1-33.
29. Muranishi S. Absorption barriers and absorption promoters in the intestine. Topics in Pharmaceutical Science 1987, 445-455. Elsevier B.V., Amsterdam. D.D. Breimer, P. Speiser (Eds.).
30. Oren Z., Shai Y. Selective lysis of bacteria but not mammalian cells by diastereomers of melittin: structure-function study. Biochemistry 1997, 36(7):1826-1835.
31. Pratt J.P., et al. Melittin-induced membrane permeability: a nonosmotic mechanism of cell death. In Vitro Cell Dev. Biol. Anim. 2005, 41(10):349-355.
32. Raghuraman H., Chattopadhyay A. Melittin: a membrane-active peptide with diverse functions. Biosci. Rep. 2007, 27(4-5):189-223.
33. Schasteen C.S., Donovan M.G., Cogburn J.N. A novel in vitro screen to discover agents which increase the absorption of molecules across the intestinal epithelium. J. Contr. Rel. 1992, 21(1-3):49-62.
34. Shin S.Y., et al. Antibacterial, antitumor and hemolytic activities of alpha-helical antibiotic peptide, P18 and its analogs. J. Pept. Res. 2001, 58(6):504-514.
35. Subbalakshmi C., Nagaraj R., Sitaram N. Biological activities of C-terminal 15-residue synthetic fragment of melittin: design of an analog with improved antibacterial activity. FEBS Lett. 1999, 448(1):62-66.
36. Swenson S.E., Curatolo W.J. (C) Means to enhance penetration: (2) Intestinal permeability enhancement for proteins, peptides and other polar drugs: mechanisms and potential toxicity. Adv. Drug Del. Rev. 1992, 8(1):39-92.
37. Tavelin S., et al. A new principle for tight junction modulation based on occludin peptides. Mol. Pharmacol. 2003, 64(6):1530-1540.
38. Tillman L.G., Geary R.S., Hardee G.E. Oral delivery of antisense oligonucleotides in man. J. Pharm. Sci. 2008, 97(1):225-236.
39. Tosteson M.T., Holmes S.J., Razin M., Tosteson D.C. Melittin lysis of red cells. J. Membr. Biol. 1985, 87(1):35-44.
40. Wade D., et al. All-D amino acid-containing channel-forming antibiotic peptides. Proc. Natl. Acad. Sci. U.S.A. 1990, 87(12):4761-4765.
41. Yan H., Li S., Sun X., Mi H., He B. Individual substitution analogs of Mel(12-26), melittin's C-terminal 15-residue peptide: their antimicrobial and hemolytic actions. FEBS Lett. 2003, 554(1-2):100-104.
42. Yang L., Harroun T.A., Weiss T.M., Ding L., Huang H.W. Barrel-stave model or toroidal model? A case study on melittin pores. Biophys. J. 2001, 81(3):1475-1485.
43. Zhu W.L., et al. Substitution of the leucine zipper sequence in melittin with peptoid residues affects self-association, cell selectivity, and mode of action. Biochim. Biophys. Acta 2007, 1768(6):1506-1517.