Self-assembled phenylalanine-α,β-dehydrophenylalanine nanotubes for sustained intravitreal delivery of a multi-targeted tyrosine kinase inhibitor

Journal of Controlled Release

Volumn 172, Issue 3, 2013, Pages 1151-1160

  Panda, Jiban J ^a,b   Yandrapu, Sarath ^b   Kadam, Rajendra S ^b   Chauhan, Virander S ^a   Kompella, Uday B ^b,c,d  

^a INTERNATIONAL CENTRE FOR GENETIC ENGINEERING AND BIOTECHNOLOGY   (Italy)

^b UNIVERSITY OF COLORADO   (United States)

^c UNIVERSITY OF COLORADO SCHOOL OF MEDICINE   (United States)

^d The University of Colorado Denver   (United States)

Author keywords

Dipeptide nanotubes; Drug delivery; Noninvasive ocular fluorophotometry; Pazopanib; Self assembly

Indexed keywords

DEHYDROPHENYLALANINE; DI-PEPTIDES; FLUOROPHOTOMETRY; INTRAVITREAL INJECTION; MASS SPECTROMETRY ANALYSIS; PAZOPANIB; RETINAL PIGMENT EPITHELIAL CELLS; TYROSINE KINASE INHIBITOR;

AMINO ACIDS; DRUG DELIVERY; ENZYME INHIBITION; GAGES; IMPLANTS (SURGICAL); LOADING; MASS SPECTROMETRY; NEEDLES; PEPTIDES; SELF ASSEMBLY;

NANOTUBES;

FLUORESCENT DYE; NANOTUBE; PAZOPANIB; PHENYLALANINE ALPHA,BETA DEHYDROPHENYLALANINE NANOTUBE; UNCLASSIFIED DRUG; VISUAL PIGMENT;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED DRUG RELEASE; CONTROLLED STUDY; DISPERSION; DRUG CYTOTOXICITY; DRUG DELIVERY DEVICE; ELECTRON MICROSCOPY; EPITHELIUM CELL; FLUOROPHOTOMETRY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MALE; MASS SPECTROMETRY; NANOENCAPSULATION; NONHUMAN; OPHTHALMIC DRUG DELIVERY DEVICE; PARTICLE SIZE; PRIORITY JOURNAL; RAT; SYRINGE NEEDLE; VITREOUS BODY; ZETA POTENTIAL;

DIPEPTIDE NANOTUBES; DRUG DELIVERY; NONINVASIVE OCULAR FLUOROPHOTOMETRY; PAZOPANIB; SELF-ASSEMBLY;

ANIMALS; DELAYED-ACTION PREPARATIONS; INTRAVITREAL INJECTIONS; NANOTUBES; PHENYLALANINE; PROTEIN KINASE INHIBITORS; PROTEIN-TYROSINE KINASES; PYRIMIDINES; RATS; RETINA; SULFONAMIDES; VITREOUS BODY;

EID: 84887577311     PISSN: 01683659     EISSN: 18734995     Source Type: Journal    
DOI: 10.1016/j.jconrel.2013.09.016     Document Type: Article

References (57)

1. N.M. Bressler Age-related macular degeneration is the leading cause of blindness JAMA 291 2004 1900 1901 (Pubitemid 38509505)
2. M.J. Tolentino Current molecular understanding and future treatment strategies for pathologic ocular neovascularization Curr. Mol. Med. 9 2009 973 981
3. I. Kozak, A. Dean, T.M. Clark, I. Falkenstein, and W.R. Freeman Prefilled syringe needles versus standard removable needles for intravitreous injection Retina 26 2006 679 683 (Pubitemid 44620370)
4. H.E. Grossniklaus, and W.R. Green Choroidal neovascularization Am. J. Ophthalmol. 137 2004 496 503 (Pubitemid 38328642)
5. P.J. Rosenfeld, D.M. Brown, J.S. Heier, D.S. Boyer, P.K. Kaiser, C.Y. Chung, and R.Y. Kim Ranibizumab for neovascular age-related macular degeneration N. Engl. J. Med. 355 2006 1419 1431 (Pubitemid 44511557)
6. D.J. Pieramici, and M.D. Rabena Anti-VEGF therapy: comparison of current and future agents Eye (Lond.) 22 2008 1330 1336
7. N. Ferrara Vascular endothelial growth factor and age-related macular degeneration: from basic science to therapy Nat. Med. 16 2010 1107 1111
8. K. Takahashi, Y. Saishin, Y. Saishin, A.G. King, R. Levin, and P.A. Campochiaro Suppression and regression of choroidal neovascularization by the multitargeted kinase inhibitor pazopanib Arch. Ophthalmol. 127 2009 494 499
9. Y. Yafai, X.M. Yang, M. Niemeyer, A. Nishiwaki, J. Lange, P. Wiedemann, A. King, T. Yasukawa, and W. Eichler Anti-angiogenic effects of the receptor tyrosine kinase inhibitor, pazopanib, on choroidal neovascularization in rats Eur. J. Pharmacol. 666 2011 12 18
10. A. Thakur, R.I. Scheinman, V.R. Rao, and U.B. Kompella Pazopanib, a multitargeted tyrosine kinase inhibitor, reduces diabetic retinal vascular leukostasis and leakage Microvasc. Res. 82 2011 346 350
11. H.I. Hurwitz, A. Dowlati, S. Saini, S. Savage, A.B. Suttle, D.M. Gibson, J.P. Hodge, E.M. Merkle, and L. Pandite Phase I trial of pazopanib in patients with advanced cancer Clin. Cancer Res. 15 2009 4220 4227
12. K. Podar, G. Tonon, M. Sattler, Y.T. Tai, S. Legouill, H. Yasui, K. Ishitsuka, S. Kumar, R. Kumar, L.N. Pandite, T. Hideshima, D. Chauhan, and K.C. Anderson The small-molecule VEGF receptor inhibitor pazopanib (GW786034B) targets both tumor and endothelial cells in multiple myeloma Proc. Natl. Acad. Sci. U. S. A. 103 2006 19478 19483 (Pubitemid 46026056)
13. C.N. Sternberg, I.D. Davis, J. Mardiak, C. Szczylik, E. Lee, J. Wagstaff, C.H. Barrios, P. Salman, O.A. Gladkov, A. Kavina, J.J. Zarba, M. Chen, L. McCann, L. Pandite, D.F. Roychowdhury, and R.E. Hawkins Pazopanib in locally advanced or metastatic renal cell carcinoma: results of a randomized phase III trial J. Clin. Oncol. 28 2010 1061 1068
14. R. Gaudana, H.K. Ananthula, A. Parenky, and A.K. Mitra Ocular drug delivery AAPS J. 12 2010 348 360
15. T. Loftsson, H.H. Sigurdsson, F. Konradsdottir, S. Gisladottir, P. Jansook, and E. Stefansson Topical drug delivery to the posterior segment of the eye: anatomical and physiological considerations Pharmazie 63 2008 171 179 (Pubitemid 351449926)
16. J.L. Davis, B.C. Gilger, and M.R. Robinson Novel approaches to ocular drug delivery Curr. Opin. Mol. Ther. 6 2004 195 205
17. P.M. Hughes, O. Olejnik, J.E. Chang-Lin, and C.G. Wilson Topical and systemic drug delivery to the posterior segments Adv. Drug Deliv. Rev. 57 2005 2010 2032 (Pubitemid 41740793)
18. T.R. Thrimawithana, S. Young, C.R. Bunt, C. Green, and R.G. Alany Drug delivery to the posterior segment of the eye Drug Discov. Today 16 2011 270 277
19. R.D. Jager, L.P. Aiello, S.C. Patel, and E.T. Cunningham Jr. Risks of intravitreous injection: a comprehensive review Retina 24 2004 676 698 (Pubitemid 39391758)
20. Y.E. Choonara, V. Pillay, M.P. Danckwerts, T.R. Carmichael, and L.C. du Toit A review of implantable intravitreal drug delivery technologies for the treatment of posterior segment eye diseases J. Pharm. Sci. 99 2010 2219 2239
21. J.L. Bourges, C. Bloquel, A. Thomas, F. Froussart, A. Bochot, F. Azan, R. Gurny, D. BenEzra, and F. Behar-Cohen Intraocular implants for extended drug delivery: therapeutic applications Adv. Drug. Deliv. Rev. 58 2006 1182 1202 (Pubitemid 44794429)
22. S.S. Lee, P. Hughes, A.D. Ross, and M.R. Robinson Biodegradable implants for sustained drug release in the eye Pharm. Res. 27 2010 2043 2053
23. B.D. Kuppermann, M.S. Blumenkranz, J.A. Haller, G.A. Williams, D.V. Weinberg, C. Chou, and S.M. Whitcup Randomized controlled study of an intravitreous dexamethasone drug delivery system in patients with persistent macular edema Arch. Ophthalmol. 125 2007 309 317 (Pubitemid 46425557)
24. T.J. Smith, P.A. Pearson, D.L. Blandford, J.D. Brown, K.A. Goins, J.L. Hollins, E.T. Schmeisser, P. Glavinos, L.B. Baldwin, and P. Ashton Intravitreal sustained-release ganciclovir Arch. Ophthalmol. 110 1992 255 258
25. G.E. Sanborn, R. Anand, R.E. Torti, S.D. Nightingale, S.X. Cal, B. Yates, P. Ashton, and T. Smith Sustained-release ganciclovir therapy for treatment of cytomegalovirus retinitis. Use of an intravitreal device Arch. Ophthalmol. 110 1992 188 195
26. E.B. Rodrigues, A. Grumann Jr., F.M. Penha, H. Shiroma, E. Rossi, C.H. Meyer, V. Stefano, M. Maia, O. Magalhaes Jr., and M.E. Farah Effect of needle type and injection technique on pain level and vitreal reflux in intravitreal injection J. Ocul. Pharmacol. Ther. 27 2011 197 203
27. V.S. De Stefano, J.J. Abechain, L.F. de Almeida, D.M. Verginassi, E.B. Rodrigues, E. Freymuller, M. Maia, O. Magalhaes, Q.D. Nguyen, and M.E. Farah Experimental investigation of needles, syringes and techniques for intravitreal injections Clin. Exp. Ophthalmol. 39 2011 236 242
28. R.C. Nagarwal, S. Kant, P.N. Singh, P. Maiti, and J.K. Pandit Polymeric nanoparticulate system: a potential approach for ocular drug delivery J. Control. Release 136 2009 2 13
29. K.S. Soppimath, T.M. Aminabhavi, A.R. Kulkarni, and W.E. Rudzinski Biodegradable polymeric nanoparticles as drug delivery devices J. Control. Release 70 2001 1 20 (Pubitemid 32144788)
30. S.J. Kang, C. Durairaj, U.B. Kompella, J.M. O'Brien, and H.E. Grossniklaus Subconjunctival nanoparticle carboplatin in the treatment of murine retinoblastoma Arch. Ophthalmol. 127 2009 1043 1047
31. H. Gupta, M. Aqil, R.K. Khar, A. Ali, A. Bhatnagar, and G. Mittal Sparfloxacin-loaded PLGA nanoparticles for sustained ocular drug delivery Nanomedicine 6 2010 324 333
32. H.A. Liu, Y.L. Liu, Z.Z. Ma, J.C. Wang, and Q. Zhang A lipid nanoparticle system improves siRNA efficacy in RPE cells and a laser-induced murine CNV model Invest. Ophthalmol. Vis. Sci. 52 2011 4789 4794
33. S. Wadhwa, R. Paliwal, S.R. Paliwal, and S.P. Vyas Nanocarriers in ocular drug delivery: an update review Curr. Pharm. Des. 15 2009 2724 2750
34. A. Seyfoddin, J. Shaw, and R. Al-Kassas Solid lipid nanoparticles for ocular drug delivery Drug Deliv. 17 2010 467 489
35. M. Gupta, A. Bagaria, A. Mishra, P. Mathur, A. Basu, S. Ramakumar, and V.S. Chauhan Self-assembly of a dipeptide-containing conformationally restricted dehydrophenylalanine residue to form ordered nanotubes Adv. Mater. 19 2007 858 861 (Pubitemid 46932818)
36. A. Mishra, J.J. Panda, A. Basu, and V.S. Chauhan Nanovesicles based on self-assembly of conformationally constrained aromatic residue containing amphiphilic dipeptides Langmuir 24 2008 4571 4576 (Pubitemid 351725135)
37. J.J. Panda, A. Kaul, S. Alam, A.K. Babbar, A.K. Mishra, and V.S. Chauhan Designed peptides as model self-assembling nanosystems: characterization and potential biomedical applications Ther. Deliv. 2 2011 193 204
38. J.J. Panda, A. Kaul, S. Kumar, S. Alam, A.K. Mishra, G.C. Kundu, and V.S. Chauhan Modified dipeptide-based nanoparticles: vehicles for targeted tumor drug delivery Nanomedicine (London) 2013 (Epub., PMID: 23398497)
39. J.J. Panda, A. Mishra, A. Basu, and V.S. Chauhan Stimuli responsive self-assembled hydrogel of a low molecular weight free dipeptide with potential for tunable drug delivery Biomacromolecules 9 2008 2244 2250
40. M.L. English, and C.H. Stammer The enzyme stability of dehydropeptides Biochem. Biophys. Res. Commun. 83 1978 1464 1467 (Pubitemid 9009275)
41. D. Mendel, J.A. Ellman, Z. Chang, D.L. Veenstra, P.A. Kollman, and P.G. Schultz Probing protein stability with unnatural amino acids Science 256 1992 1798 1802
42. D.K. Sharma, D. King, P. Oma, and C. Merchant Micro-flow imaging: flow microscopy applied to sub-visible particulate analysis in protein formulations AAPS J. 12 2010 455 464
43. M. Reches, and E. Gazit Casting metal nanowires within discrete self-assembled peptide nanotubes Science 300 2003 625 627 (Pubitemid 36520583)
44. E. Gazit Self-assembled peptide nanostructures: the design of molecular building blocks and their technological utilization Chem. Soc. Rev. 36 2007 1263 1269
45. Y. Jang, and I. Kim Severe hepatotoxicity after sevoflurane anesthesia in a child with mild renal dysfunction Paediatr. Anaesth. 15 2005 1140 1144 (Pubitemid 43965399)
46. G.D. Nielsen, M.H. Abraham, L.F. Hansen, M. Hammer, C.J. Cooksey, J. Andonian-Haftvan, and Y. Alarie Sensory irritation mechanisms investigated from model compounds: trifluoroethanol, hexafluoroisopropanol and methyl hexafluoroisopropyl ether Arch. Toxicol. 70 1996 319 328 (Pubitemid 26096509)
47. R.C. Rowe, P.J. Sheskey, and M.E. Quinn Handbook of Pharmaceutical Excipients 6th edition 2009 Pharmaceutical press
48. B.Y. Shekunov, P. Chattopadhyay, H.H. Tong, and A.H. Chow Particle size analysis in pharmaceutics: principles, methods and applications Pharm. Res. 24 2007 203 227 (Pubitemid 46072181)
49. T.M. Crowder, A.J. Hickey, and M.D. Louey N. Orr, A Guide to Pharmaceutical Particulate Science 2003 Interpharm/CRC press Boca Raton London New York Washington, D.C
50. S. Scanlon, and A. Aggeli Self-assembling peptide nanotubes NanoToday 3 2008 22 30 (Pubitemid 351781281)
51. N.S. de Groot, T. Parella, F.X. Aviles, J. Vendrell, and S. Ventura Ile-phe dipeptide self-assembly: clues to amyloid formation Biophys. J. 92 2007 1732 1741 (Pubitemid 46393484)
52. S. Vauthey, S. Santoso, H. Gong, N. Watson, and S. Zhang Molecular self-assembly of surfactant-like peptides to form nanotubes and nanovesicles Proc. Natl. Acad. Sci. U. S. A. 99 2002 5355 5360 (Pubitemid 34411552)
53. H. Heimann Intravitreal Injections: Techniques and Sequelae in Medical Retina F.G. Holz, R.F. Spaide, 2007 Springer Verlag Berlin, Heidelberg
54. N.B. Shelke, R.S. Kadam, P. Tyagi, V.R. Rao, and U.B. Kompella Intravitreal poly(l-lactide) microparticles sustain retinal and choroidal delivery of TG-0054, a hydrophilic drug intended for neovascular diseases Drug Deliv. Transl. Res. 1 2011 76 90
55. J. Emami In vitro-in vivo correlation: from theory to applications J. Pharm. Pharm. Sci. 9 2006 169 189
56. J.S. Rudra, T. Sun, K.C. Bird, M.D. Daniels, J.Z. Gasiorowski, A.S. Chong, and J.H. Collier Modulating adaptive immune responses to peptide self-assemblies ACS Nano 6 2012 1557 1564
57. Y. Lu, J. Yang, and E. Sega Issues related to targeted delivery of proteins and peptides AAPS J. 8 2006 E466 E478