Mucoadhesive acrylated block copolymers micelles for the delivery of hydrophobic drugs

Colloids and Surfaces B: Biointerfaces

Volumn 139, Issue , 2016, Pages 42-51

  Eshel Green, Tal ^a   Bianco Peled, Havazelet ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

Acrylated polymers; Hydrophobic drugs; Micelles; Mucoadhesion; Nano; Synergism

Indexed keywords

ADDITION REACTIONS; BLOCK COPOLYMERS; CRITICAL MICELLE CONCENTRATION; DYNAMIC LIGHT SCATTERING; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; HYDRATION; HYDROPHOBICITY; LIGHT SCATTERING; MAGNETIC LEVITATION VEHICLES; NUCLEAR MAGNETIC RESONANCE; TRANSMISSION ELECTRON MICROSCOPY; VISCOSITY; X RAY SCATTERING;

ACRYLATED POLYMERS; HYDROPHOBIC DRUG; MUCOADHESION; NANO; SYNERGISM;

MICELLES;

COPOLYMER; INDOMETACIN; MUCOADHESIVE ACRYLATED BLOCK COPOLYMER MICELLE; STOMACH MUCIN; UNCLASSIFIED DRUG; ACRYLIC ACID DERIVATIVE; DRUG CARRIER; MICELLE; POLOXAMER;

ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; CRITICAL MICELLE CONCENTRATION; DRUG DELIVERY SYSTEM; DRUG DOSAGE FORM COMPARISON; DRUG RELEASE; IN VITRO STUDY; LIGHT SCATTERING; MICELLIZATION; MICHAEL ADDITION; MUCOADHESION; PARTICLE SIZE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SHEAR RATE; TRANSMISSION ELECTRON MICROSCOPY; X RAY CRYSTALLOGRAPHY; ANIMAL; CHEMICAL PHENOMENA; CHEMISTRY; DRUG FORMULATION; ISOLATION AND PURIFICATION; KINETICS; MICELLE; PIG; VISCOSITY;

ACRYLATES; ANIMALS; DRUG CARRIERS; DRUG COMPOUNDING; DRUG LIBERATION; GASTRIC MUCINS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INDOMETHACIN; KINETICS; MICELLES; POLOXAMER; SWINE; VISCOSITY;

EID: 84949672977     PISSN: 09277765     EISSN: 18734367     Source Type: Journal    
DOI: 10.1016/j.colsurfb.2015.11.044     Document Type: Article

References (54)

1. Shaikh R., Raj Singh T.R., Garland M.J., Woolfson A.D., Donnelly R.F. Mucoadhesive drug delivery systems. J. Pharm. Bioallied Sci. 2010, 3:89-100. 10.4103/0975-7406.76478.
2. Sosnik A., Das Neves J., Sarmento B. Mucoadhesive polymers in the design of nano-drug delivery systems for administration by non-parenteral routes: a review. Prog. Polym. Sci. 2014, 39:2030-2075.
3. Boddupalli B.M., Mohammed Z.N.K., Nath R.A., Banji D. Mucoadhesive drug delivery system: an overview. J. Adv. Pharm. Technol. Res. 2010, 1:381-387. 10.4103/0110-5558.76436.
4. Lian H., Zhang T., Sun J., Liu X., Ren G., Kou L., et al. Enhanced oral delivery of paclitaxel using acetylcysteine functionalized chitosan-vitamin E succinate nanomicelles based on a mucus bioadhesion and penetration mechanism. Mol. Pharm. 2013, 10:3447-3458. 10.1021/mp400282r.
5. Bernkop-Schnürch A., Krauland A.H., Leitner V.M., Palmberger T. Thiomers: potential excipients for non-invasive peptide delivery systems. Int. Assoc. Pharm. Technol. 2004, 58:253-263. 10.1016/j.ejpb.2004.03.032.
6. Davidovich-Pinhas M., Harari O., Bianco-Peled H. Evaluating the mucoadhesive properties of drug delivery systems based on hydrated thiolated alginate. J. Control. Release 2009, 136:38-44.
7. Dufresne M.-Hã., Gauthier M.A., Leroux J.-C. Thiol-functionalized polymeric micelles: from molecular recognition to improved mucoadhesion. Bioconjug. Chem. 2005, 16:1027-1033. 10.1021/bc050007b.
8. Štorha A., Mun E.A., Khutoryanskiy V.V. Synthesis of thiolated and acrylated nanoparticles using thiol-ene click chemistry: towards novel mucoadhesive materials for drug delivery. RSC Adv. 2013, 3:12275-12279.
9. Davidovich-Pinhas M., Bianco-Peled H. Novel mucoadhesive system based on sulfhydryl-acrylate interactions. J. Mater. Sci. Mater. Med. 2010, 21:2027-2034.
10. Davidovich-Pinhas M., Bianco-Peled H. Alginate-PEGAc: a new mucoadhesive polymer. Acta Biomater. 2011, 7:625-633.
11. Davidovich-Pinhas M., Bianco-Peled H. Physical and structural characteristics of acrylated poly(ethylene glycol)-alginate conjugates. Acta Biomater. 2011, 7:2817-2825.
12. Peppas N.A., Huang Y. Nanoscale technology of mucoadhesive interactions. Adv. Drug Deliv. Rev. 2004, 56:1675-1687. 10.1016/j.addr.2004.03.001.
13. das Neves J., Bahia M.F., Amiji M.M., Sarmento B. Mucoadhesive nanomedicines: characterization and modulation of mucoadhesion at the nanoscale. Expert Opin. Drug Deliv. 2011, 8:1085-1104. 10.1517/17425247.2011.586334.
14. Torchilin V.P. Micellar nanocarriers: pharmaceutical perspectives. Pharm. Res. 2007, 24:1-16. 10.1007/s11095-006-9132-0.
15. Sosnik A., Menaker Raskin M. Polymeric micelles in mucosal drug delivery: challenges towards clinical translation. Biotechnol. Adv. 2015.
16. Bonferoni M.C., Sandri G., Ferrari F., Rossi S., Larghi V., Zambito Y., et al. Comparison of different in vitro and ex vivo methods to evaluate mucoadhesion of glycol-palmitoyl chitosan micelles. J. Drug Deliv. Sci. Technol. 2010, 20:419-424. 10.1016/S1773-2247(10)50073-X.
17. Bromberg L., Temchenko M., Alakhov V., Hatton T.A. Bioadhesive properties and rheology of polyether-modified poly(acrylic acid) hydrogels. Int. J. Pharm. 2004, 282:45-60. 10.1016/j.ijpharm.2004.05.030.
18. Yang J., Yan J., Zhou Z., Amsden B.G. Dithiol-PEG-PDLLA micelles: preparation and evaluation as potential topical ocular delivery vehicle. Biomacromolecules 2014, 15:1346-1354. 10.1021/bm4018879.
19. La S.B., Okano T., Kataoka K. Preparation and characterization of the micelle-forming polymeric drug indomethacin-incorporated poly(ethylene oxide) poly(-benzyl-l-aspartate) block copolymer micelles. J. Pharm. Sci. 1996, 85:85-90. 10.1021/js950204r.
20. Aw M., Gulati K., Losic D. Controlling drug release from titania nanotube arrays using polymer nanocarriers and biopolymer coating. Sci. Res. 2011, 2:477-484.
21. ® F127: micellar assembly, gelation and partitioning. Int. J. Pharm. 2004, 278:361-377.
22. Elchidana P.A., Deshpande S.G. Microporous membrane drug delivery system for indomethacin. J. Control. Release 1999, 59:279-285. 10.1016/S0168-3659(98)00162-X.
23. Halstenberg S., Panitch A., Rizzi S., Hall H., Hubbell J.A. Biologically engineered protein-graft-poly(ethylene glycol) hydrogels: a cell adhesive and plasmin-degradable biosynthetic material for tissue repair. Biomacromolecules 2002, 3:710-723. 10.1021/bm015629o.
24. Sun Y., Liu S., Du G., Gao G., Fu J. Multi-responsive and tough hydrogels based on triblock copolymer micelles as multi-functional macro-crosslinkers. Chem. Commun. 2015, 51:8512-8515. 10.1039/C4CC10094H.
25. Kočevar-Nared J., Kristl J., Šmid-Korbar J. Comparative rheological investigation of crude gastric mucin and natural gastric mucus. Biomaterials 1997, 18:677-681. 10.1016/S0142-9612(96)00180-9.
26. Menchicchi B., Fuenzalida J.P., Bobbili K.B., Hensel A., Swamy M.J., Goycoolea F.M. Structure of chitosan determines its interactions with mucin. Biomacromolecules 2014, 15:3550-3558. 10.1021/bm5007954.
27. Menchicchi B., Fuenzalida J.P., Hensel A., Swamy M.J., David L., Rochas C., et al. Biophysical analysis of the molecular interactions between polysaccharides and mucin. Biomacromolecules 2015, 16:924-935. 10.1021/bm501832y.
28. Fefelova N.A., Nurkeeva Z.S., Mun G.A., Khutoryanskiy V.V. Mucoadhesive interactions of amphiphilic cationic copolymers based on [2-(methacryloyloxy) ethyl]trimethylammonium chloride. Int. J. Pharm. 2007, 339:25-32. 10.1016/j.ijpharm.2007.02.019.
29. Mantle M., Stewart G., Zayas G., King M. The disulphide-bond content and rheological properties of intestinal mucins from normal subjects and patients with cystic fibrosis. Biochem. J. 1990, 266:597-604.
30. Josef E. Controlled Release of Hydrophobic Drugs from Nanocarriers Embedded in Alginate Hydrogels 2013, Technion.
31. Pedersen J.S. Analysis of small-angle scattering data from colloids and polymer solutions: modeling and least-squares fitting. Adv. Colloid Interface Sci. 1997, 70:171-210.
32. Pedersen J.S. Form factors of block copolymer micelles with spherical, ellipsoidal and cylindrical cores. J. Appl. Crystallogr. 2000, 33:637-640. 10.1107/S0021889899012248.
33. Pedersen J.S., Gerstenberg M.C. Scattering form factor of block copolymer micelles. Macromolecules 1996, 29:1363-1365. 10.1021/ma9512115.
34. Lopes J.R., Loh W. Investigation of self-assembly and micelle polarity for a wide range of ethylene oxide-propylene oxide-ethylene oxide block copolymers in water. Langmuir 1998, 14:750-756.
35. Wan D.-H., Zheng O., Zhou Y., Wu L.-Y. Solubilization of ibuprofen in pluronic block copolymer F127 micelles. Wuli Huaxue Xuebao/Acta Phys. Chim. Sin. 2010, 26:3243-3248.
36. Kumar B., Meher J.G., Gupta A., Pawar V.K., Singh Y., Chourasia M.K. Delivery of methotrexate executed by engineered polymeric micelles intended to improve chemotherapy. J. Biomater. Tissue Eng. 2014, 4:700-709.
37. Koifman N., Schnabel-Lubovsky M., Talmon Y. Nanostructure formation in the lecithin/isooctane/water system. J. Phys. Chem. B 2013, 117:9558-9567. 10.1021/jp405490q.
38. Zhang W., Shi Y., Chen Y., Yu S., Hao J., Luo J., et al. Enhanced antitumor efficacy by paclitaxel-loaded Pluronic P123/F127 mixed micelles against non-small cell lung cancer based on passive tumor targeting and modulation of drug resistance. Eur. J. Pharm. Biopharm. 2010, 75:341-353.
39. Chen L., Sha X., Jiang X., Chen Y., Ren Q., Fang X. Pluronic P105/F127 mixed micelles for the delivery of docetaxel against taxol-resistant non-small cell lung cancer: optimization and in vitro, in vivo evaluation. Int. J. Nanomed. 2013, 8:73-84. 10.2147/IJN.S38221.
40. Goldmints I., Yu G., Booth C., Smith K.A., Hatton T.A. Structure of (deuterated PEO)(PPO)(deuterated PEO) block copolymer micelles as determined by small angle neutron scattering. Langmuir 1999, 15:1651-1656. 10.1021/la9807006.
41. ® RS 100/cyclodextrin nanoparticles for the transmucosal administration of glutathione. Eur. J. Pharm. Biopharm. 2009, 72:509-520.
42. Chayed S., Winnik F.M. In vitro evaluation of the mucoadhesive properties of polysaccharide-based nanoparticulate oral drug delivery systems. Eur. J. Pharm. Biopharm. 2007, 65:363-370. 10.1016/j.ejpb.2006.08.017.
43. Agüeros M., Zabaleta V., Espuelas S., Campanero M.A., Irache J.M. Increased oral bioavailability of paclitaxel by its encapsulation through complex formation with cyclodextrins in poly(anhydride) nanoparticles. J. Control. Release 2010, 145:2-8.
44. Grabovac V., Guggi D., Bernkop-Schnürch A. Comparison of the mucoadhesive properties of various polymers. Adv. Drug Deliv. Rev. 2005, 57:1713-1723.
45. Ivarsson D., Wahlgren M. Comparison of in vitro methods of measuring mucoadhesion: ellipsometry, tensile strength and rheological measurements. Colloids Surf. B Biointerfaces 2012, 92:353-359.
46. Pohmann R. Physical basics of NMR. Vivo NMR Imaging 2011, 3-21. Humana Press. 10.1007/978-1-61779-219-9_1. L. Schröder, C. Faber (Eds.).
47. Ding H., Yong K.-T., Law W.-C., Roy I., Hu R., Wu F., et al. Non-invasive tumor detection in small animals using novel functional pluronic nanomicelles conjugated with anti-mesothelin antibody. Nanoscale 2011, 3:1813-1822. 10.1039/C1NR00001B.
48. Hassan E., Gallo J. A simple rheological method for the in vitro assessment of mucin-polymer bioadhesive bond strength. Pharm. Res. 1990, 7:491-495. 10.1023/A:1015812615635.
49. Thirawong N., Kennedy R.A., Sriamornsak P. Viscometric study of pectin-mucin interaction and its mucoadhesive bond strength. Carbohydr. Polym. 2008, 71:170-179.
50. Bansil R., Stanley E., Lamont J.T. Mucin biophysics. Annu. Rev. Physiol. 1995, 57:635-657. 10.1146/annurev.ph.57.030195.003223.
51. Prud'homme R.K., Wu G., Schneider D.K. Structure and rheology studies of poly(oxyethylene-oxypropylene-oxyethylene) aqueous solution. Langmuir 1996, 12:4651-4659. 10.1021/la951506b.
52. Dedinaite A., Bastardo L. Interactions between mucin and surfactants at solid liquid interfaces. Langmuir 2002, 18:9383-9392. 10.1021/la0259813.
53. Lafitte G., Thuresson K., Söderman O. Mixtures of mucin and oppositely charged surfactant aggregates with varying charge density. Phase behavior, association, and dynamics. Langmuir 2005, 21:7097-7104. 10.1021/la0472807.
54. Nokhodchi A., Javadzadeh Y., Siahi-Shadbad M., Barzegar-Jalali M. The effect of type and concentration of vehicles on the dissolution rate of a poorly soluble drug (indomethacin) from liquisolid compacts. J. Pharm. Pharm. Sci. 2005, 8:18-25.