PEGylation of a proprotein convertase peptide inhibitor for vaginal route of drug delivery: In vitro bioactivity, stability and in vivo pharmacokinetics

Peptides

Volumn 38, Issue 2, 2012, Pages 266-274

  Ho, Huiting ^a,b   Nero, Tracy L ^c   Singh, Harmeet ^a   Parker, Michael W ^c,d   Nie, Guiying ^a  

^a HUDSON INSTITUTE OF MEDICAL RESEARCH   (Australia)

^b MONASH UNIVERSITY   (Australia)

^c ST VINCENT'S INSTITUTE OF MEDICAL RESEARCH   (Australia)

^d UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

Decidualization; PEGylation; Pharmokinetic; Proprotein convertase

Indexed keywords

PROPROTEIN CONVERTASE 6; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CELL CULTURE; DECIDUALIZATION; DRUG ACTIVITY; DRUG STABILITY; ENDOMETRIUM CELL; FEMALE; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NIDATION; NONHUMAN; PREDICTION; PRIORITY JOURNAL; STROMA CELL; TISSUE DISTRIBUTION; UTERINE CERVIX; UTERUS; VAGINA; VAGINA MUCOSA;

ADMINISTRATION, INTRAVAGINAL; ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DELIVERY SYSTEMS; DRUG STABILITY; FEMALE; HUMANS; MICE; MICE, INBRED C57BL; OLIGOPEPTIDES; POLYETHYLENE GLYCOLS; PROPROTEIN CONVERTASES; RECOMBINANT PROTEINS; SERINE ENDOPEPTIDASES; SERINE PROTEINASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION; VAGINA;

ANIMALIA; MUS;

EID: 84868699783     PISSN: 01969781     EISSN: 18735169     Source Type: Journal    
DOI: 10.1016/j.peptides.2012.09.014     Document Type: Article

References (50)

1. E.D. Anderson, L. Thomas, J.S. Hayflick, and G. Thomas Inhibition of HIV-1 gp160-dependent membrane fusion by a furin-directed alpha 1-antitrypsin variant J Biol Chem 268 1993 24887 24891
2. C. Bulletti, D. de Ziegler, B. de Moustier, V. Polli, G. Bolelli, and F. Franceschetti Uterine contractility: vaginal administration of the beta-adrenergic agonist, terbutaline. Evidence of direct vagina-to-uterus transport Ann N Y Acad Sci 943 2001 163 171
3. E. Cicinelli, M. Cignarelli, S. Sabatelli, F. Romano, L.M. Schonauer, and R. Padovano Plasma concentrations of progesterone are higher in the uterine artery than in the radial artery after vaginal administration of micronized progesterone in an oil-based solution to postmenopausal women Fertil Steril 69 1998 471 473
4. E. Cicinelli, and D. de Ziegler Transvaginal progesterone: evidence for a new functional 'portal system' flowing from the vagina to the uterus Hum Reprod Update 5 1999 365 372
5. E. Cicinelli, D. de Ziegler, C. Bulletti, M.G. Matteo, L.M. Schonauer, and P. Galantino Direct transport of progesterone from vagina to uterus Obstet Gynecol 95 2000 403 406
6. E. Cicinelli, N. Einer-Jensen, M. Cignarelli, L. Mangiacotti, D. Luisi, and S. Schonauer Preferential transfer of endogenous ovarian steroid hormones to the uterus during both the follicular and luteal phases Hum Reprod 19 2004 2001 2004
7. Y. Cu, C.J. Booth, and W.M. Saltzman In vivo distribution of surface-modified PLGA nanoparticles following intravaginal delivery J Control Release 156 2011 258 264
8. D. De Ziegler, C. Bulletti, B. De Monstier, and A.S. Jaaskelainen The first uterine pass effect Ann N Y Acad Sci 828 1997 291 299
9. E. Decroly, S. Wouters, C. Di Bello, C. Lazure, J.M. Ruysschaert, and N.G. Seidah Identification of the paired basic convertases implicated in HIV gp160 processing based on in vitro assays and expression in CD4(+) cell lines J Biol Chem 271 1996 30442 30450
10. E. Dimitriadis, L. Robb, and L.A. Salamonsen Interleukin 11 advances progesterone-induced decidualization of human endometrial stromal cells Mol Hum Reprod 8 2002 636 643
11. R.C. Edgar MUSCLE: a multiple sequence alignment method with reduced time and space complexity BMC Bioinformatics 5 2004 113
12. R.C. Edgar MUSCLE: multiple sequence alignment with high accuracy and high throughput Nucleic Acids Res 32 2004 1792 1797
13. A. Evron, S. Goldman, and E. Shalev Effect of primary human endometrial stromal cells on epithelial cell receptivity and protein expression is dependent on menstrual cycle stage Hum Reprod 26 2011 176 190
14. C. Ficicioglu, B. Gurbuz, S. Tasdemir, S. Yalti, and H. Canova High local endometrial effect of vaginal progesterone gel Gynecol Endocrinol 18 2004 240 243
15. C. Freyer, L.M. Kilpatrick, L.A. Salamonsen, and G. Nie Pro-protein convertases (PCs) other than PC6 are not tightly regulated for implantation in the human endometrium Reproduction 133 2007 1189 1197
16. M. Fugere, J. Appel, R.A. Houghten, I. Lindberg, and R. Day Short polybasic peptide sequences are potent inhibitors of PC5/6 and PC7: use of positional scanning-synthetic peptide combinatorial libraries as a tool for the optimization of inhibitory sequences Mol Pharmacol 71 2007 323 332
17. M. Fugere, and R. Day Cutting back on pro-protein convertases: the latest approaches to pharmacological inhibition Trends Pharmacol Sci 26 2005 294 301
18. B. Gellersen, I.A. Brosens, and J.J. Brosens Decidualization of the human endometrium: mechanisms, functions, and clinical perspectives Semin Reprod Med 25 2007 445 453
19. S. Hallenberger, V. Bosch, H. Angliker, E. Shaw, H.D. Klenk, and W. Garten Inhibition of furin-mediated cleavage activation of HIV-1 glycoprotein gp160 Nature 360 1992 358 361
20. S. Heng, S. Paule, B. Hardman, Y. Li, H. Singh, and A. Rainczuk Posttranslational activation of bone morphogenetic protein 2 is mediated by proprotein convertase 6 during decidualization for pregnancy establishment Endocrinology 151 2010 3909 3917
21. S. Henrich, A. Cameron, G.P. Bourenkov, R. Kiefersauer, R. Huber, and I. Lindberg The crystal structure of the proprotein processing proteinase furin explains its stringent specificity Nat Struct Biol 10 2003 520 526
22. Y. Huang, W. Leobandung, A. Foss, and N.A. Peppas Molecular aspects of muco- and bioadhesion: tethered structures and site-specific surfaces J Control Release 65 2000 63 71
23. A.N. Jain Surflex-Dock 2.1: robust performance from ligand energetic modeling, ring flexibility, and knowledge-based search J Comput Aided Mol Des 21 2007 281 306
24. K.V. Kibler, A. Miyazato, V.S. Yedavalli, A.I. Dayton, B.L. Jacobs, and G. Dapolito Polyarginine inhibits gp160 processing by furin and suppresses productive human immunodeficiency virus type 1 infection J Biol Chem 279 2004 49055 49063
25. R.A. Laskowski, M.W. Macarthur, D.S. Moss, and J.M. Thornton Procheck - a program to check the stereochemical quality of protein structures J Appl Crystallogr 26 1993 283 291
26. R. Luthy, J.U. Bowie, and D. Eisenberg Assessment of protein models with three-dimensional profiles Nature 356 1992 83 85
27. R.A. Miles, R.J. Paulson, R.A. Lobo, M.F. Press, L. Dahmoush, and M.V. Sauer Pharmacokinetics and endometrial tissue levels of progesterone after administration by intramuscular and vaginal routes: a comparative study Fertil Steril 62 1994 485 490
28. L. Miranda, J. Wolf, S. Pichuantes, R. Duke, and A. Franzusoff Isolation of the human PC6 gene encoding the putative host protease for HIV-1 gp160 processing in CD4+ T lymphocytes Proc Natl Acad Sci U S A 93 1996 7695 7700
29. G. Nie, Y. Li, M. Wang, Y.X. Liu, J.K. Findlay, and L.A. Salamonsen Inhibiting uterine PC6 blocks embryo implantation: an obligatory role for a proprotein convertase in fertility Biol Reprod 72 2005 1029 1036
30. G.Y. Nie, Y. Li, H. Minoura, J.K. Findlay, and L.A. Salamonsen Specific and transient up-regulation of proprotein convertase 6 at the site of embryo implantation and identification of a unique transcript in mouse uterus during early pregnancy Biol Reprod 68 2003 439 447
31. H. Okada, G. Nie, and L.A. Salamonsen Requirement for proprotein convertase 5/6 during decidualization of human endometrial stromal cells in vitro J Clin Endocrinol Metab 90 2005 1028 1034
32. H. Okada, I. Yamazaki, T. Yashiki, T. Shimamoto, and H. Mima Vaginal absorption of a potent luteinizing hormone-releasing hormone analogue (leuprolide) in rats IV: evaluation of the vaginal absorption and gonadotropin responses by radioimmunoassay J Pharm Sci 73 1984 298 302
33. G. Pasut, A. Guiotto, and F.M. Veronese Protein, peptide and non-peptide drug PEGylation for therapeutic application Expert Opin Ther Pat 14 6 2004 859 894
34. M.F. Powell, T. Stewart, L. Otvos Jr., L. Urge, F.C. Gaeta, and A. Sette Peptide stability in drug development II. Effect of single amino acid substitution and glycosylation on peptide reactivity in human serum Pharm Res 10 1993 1268 1273
35. M.L. Radomsky, K.J. Whaley, R.A. Cone, and W.M. Saltzman Controlled vaginal delivery of antibodies in the mouse Biol Reprod 47 1992 133 140
36. T. Reissmann, A.V. Schally, P. Bouchard, H. Riethmiiller, and J. Engel The LHRH antagonist cetrorelix: a review Hum Reprod Update 6 2000 322 331
37. L.A. Salamonsen, E. Dimitriadis, R.L. Jones, and G. Nie Complex regulation of decidualization: a role for cytokines and proteases - a review Placenta 24 Suppl. A 2003 S76 S85
38. L.A. Salamonsen, G. Nie, N.J. Hannan, and E. Dimitriadis Society for Reproductive Biology Founders' Lecture 2009. Preparing fertile soil: the importance of endometrial receptivity Reprod Fertil Dev 21 2009 923 934
39. A.P. Sayani, and Y.W. Chien Systemic delivery of peptides and proteins across absorptive mucosae Crit Rev Ther Drug Carrier Syst 13 1996 85 184
40. R.D. Schick Changes in the whole vagina of the mouse during estrus and pregnancy J Morphol 72 1943 305 329
41. N.G. Seidah, R. Day, M. Marcinkiewicz, and M. Chretien Precursor convertases: an evolutionary ancient, cell-specific, combinatorial mechanism yielding diverse bioactive peptides and proteins Ann N Y Acad Sci 839 1998 9 24
42. S.A. Shiryaev, A.G. Remacle, B.I. Ratnikov, N.A. Nelson, A.Y. Savinov, and G. Wei Targeting host cell furin proprotein convertases as a therapeutic strategy against bacterial toxins and viral pathogens J Biol Chem 282 2007 20847 20853
43. H. Singh, Y. Endo, and G. Nie Decidual HtrA3 negatively regulates trophoblast invasion during human placentation Hum Reprod 26 2011 748 757
44. N.A. Taylor, W.J. Van De Ven, and J.W. Creemers Curbing activation: proprotein convertases in homeostasis and pathology FASEB J 17 2003 1215 1227
45. F.M. Veronese, and G. Pasut PEGylation, successful approach to drug delivery Drug Discov Today 10 2005 1451 1458
46. F. Vollenweider, S. Benjannet, E. Decroly, D. Savaria, C. Lazure, and G. Thomas Comparative cellular processing of the human immunodeficiency virus (HIV-1) envelope glycoprotein gp160 by the mammalian subtilisin/kexin-like convertases Biochem J 314 Pt 2 1996 521 532
47. M. Werle, and A. Bernkop-Schnurch Strategies to improve plasma half life time of peptide and protein drugs Amino Acids 30 2006 351 367
48. C.A. White, J.G. Zhang, L.A. Salamonsen, M. Baca, W.D. Fairlie, and D. Metcalf Blocking LIF action in the uterus by using a PEGylated antagonist prevents implantation: a nonhormonal contraceptive strategy Proc Natl Acad Sci U S A 104 2007 19357 19362
49. J. Woodley Bioadhesion: new possibilities for drug administration Clin Pharmacokinet 40 2001 77 84
50. C. Zheng, G. Ma, and Z. Su Native PAGE eliminates the problem of PEG-SDS interaction in SDS-PAGE and provides an alternative to HPLC in characterization of protein PEGylation Electrophoresis 28 2007 2801 2807