Preactivated thiolated glycogen as mucoadhesive polymer for drug delivery

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 119, Issue , 2017, Pages 161-169

  Perrone, Mara ^a,b   Lopalco, Antonio ^a   Lopedota, Angela ^a   Cutrignelli, Annalisa ^a   Laquintana, Valentino ^a   Douglas, Justin ^c   Franco, Massimo ^a   Liberati, Elisa ^d   Russo, Vincenzo ^d   Tongiani, Serena ^d   Denora, Nunzio ^a   Bernkop Schnürch, Andreas ^b  

^a UNIVERSITY OF BARI   (Italy)

^b UNIVERSITY OF INNSBRUCK   (Austria)

^c UNIVERSITY OF KANSAS   (United States)

^d Università Politecnica delle Marche ACRAF Gruppo Angelini   (Italy)

Author keywords

Glycogen; Mucoadhesion; Natural dendrimer; S preactivated thiomer; Thiomers

Indexed keywords

2 MERCAPTONICOTINIC ACID; ALDEHYDE; CYSTEINE; DENDRIMER; GLYCOGEN; NICOTINIC ACID DERIVATIVE; PERIODATE SODIUM; POLYMER; THIOL; THIOL GROUP; UNCLASSIFIED DRUG; ADHESIVE AGENT; THIOGLYCOLIC ACID DERIVATIVE;

ANIMAL TISSUE; ARTICLE; CACO-2 CELL LINE; CHEMICAL MODIFICATION; CONTROLLED STUDY; CYTOTOXICITY ASSAY; DISULFIDE BOND; DRUG DELIVERY SYSTEM; FLOW KINETICS; FREEZE DRYING; IN VITRO STUDY; INTESTINE MUCOSA; MUCOADHESION; NONHUMAN; PIG; RING OPENING; VISCOSITY; WATER TRANSPORT; WEIGHT GAIN; ANIMAL; CHEMISTRY; DRUG EFFECT; HUMAN; METABOLISM; ORGAN CULTURE TECHNIQUE; PROCEDURES;

ADHESIVES; ANIMALS; CACO-2 CELLS; DRUG DELIVERY SYSTEMS; GLYCOGEN; HUMANS; INTESTINAL MUCOSA; ORGAN CULTURE TECHNIQUES; SWINE; THIOGLYCOLATES;

EID: 85020928009     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2017.06.011     Document Type: Article

References (34)

1. Morris, G.A., Ang, S., Hill, S.E., Lewis, S., Schafer, B., Nobbmann, U., Harding, S.E., Molar mass and solution conformation of branched alpha (1–4), alpha (1–6) glucans. Part I: glycogens in water. Carbohydr. Polym. 71 (2008), 101–108.
2. Rinaudo, M., Main properties and current applications of some polysaccharides as biomaterials. Polym. Int. 57 (2008), 397–430.
3. Shalaby Shalaby, W., Shah Kishore, R., Water-Soluble Polymers, Chemical Modifications of Natural Polymers and Their Technological Relevance, 1991, American Chemical Society, 74–80.
4. Perrone, M., Lopedota, A., Liberati, E., Russo, V., Cutrignelli, A., Laquintana, V., Pereira de Sousa, I., Franco, M., Tongiani, S., Denora, N., Bernkop-Schnürch, A., Natural dendrimers: synthesis and in vitrocharacterization of glycogen-cysteamine conjugates. Eur. J. Pharm. Biopharm. 115 (2017), 168–176.
5. Denora, N., Lopedota, A., Perrone, M., Laquintana, V., Iacobazzi, R.M., Millella, A., Fanizza, E., Depalo, N., Cutrignelli, A., Lopalco, A., Franco, M., Spray-dried mucoadhesives for intravesical drug delivery using N-acetylcysteine- and glutathione-glycol chitosan conjugates. Acta Biomater. 43 (2016), 170–184.
6. Lopedota, A., Cutrignelli, A., Laquintana, V., Denora, N., Iacobazzi, R.M., Perrone, M., Fanizza, E., Mastrodonato, M., Mentino, D., Lopalco, A., Depalo, N., Franco, M., Spray dried chitosan microparticles for intravesical delivery of celicoxib: preparation and characterization. Pharm. Res. 33 (2016), 2195–2208.
7. Brandt, J., Svenson, A., Carlsson, J., Drevin, H., Covalent coupling of unsaturated compounds to thiol agarose using ãeradiation: a new method for preparation of adsorbents for affinity chromatography. J. SolidePhase Biochem. 2 (1977), 105–109.
8. D.R. Grassetti. Postoperative treatment of carcinoma patients. US Patent No. 4378364, 1983.
9. Ito, T., Yeo, Y., Highley, C.B., Bellas, E., Benitez, C.A., Kohane, D.S., The prevention of peritoneal adhesions by in situ cross-linking hydrogels of hyaluronic acid and cellulose derivatives. Biomaterials 28 (2007), 975–983.
10. Bertoldo, M., Zampano, G., Suffner, L., Liberati, E., Ciardelli, F., Oxidation of glycogen “molecular nanoparticles” by periodate. Polym. Chem. 4 (2013), 653–661.
11. Hombach, J., Palmberger, T.F., Bernkop-Schnürch, A., Development and in vitro evaluation of a mucoadhesive vaginal delivery system for nystatin. J. Pharm. Sci. 98 (2009), 555–564.
12. Habeeb, A.F.S.A., A sensitive method for localization of disulfide containing peptides in column effluents. Anal. Biochem. 56 (1973), 60–65.
13. Leitner, V.M., Marschutz, M.K., Bernkop-Schnürch, A., Mucoadhesive and cohesive properties of poly (acrylic acid)–cysteine conjugates with regard to their molecular mass. Eur. J. Pharm. Sci. 18 (2003), 89–96.
14. Bonengel, S., Haupstein, S., Perera, G., Bernkop-Schnurch, A., Thiolated and S-protected hydrophobically modified cross-linked poly (acrylic acid) a new generation of multifunctional polymers. Eur. J. Pharm. Biopharm. 88 (2014), 390–396.
15. Duarte, M.L., Ferreira, M.C., Marvao, M.R., Rocha, J., Determination of the degree of acetylation of chitin materials by 13 C CP/MAS NMR spectroscopy. Int. J. Biol. Macromolec. 28 (2001), 359–363.
16. Hauptstein, S., Bonengel, S., Rohrer, J., Bernkop-Schnürch, A., Preactivated thiolated poly (methacrylic acid-co-ethyl acrylate): synthesis and evaluation of mucoadhesive potential. Eur. J. Pharm. Biopharm. 63 (2014), 132–139.
17. Bernkop-Schnürch, A., Steininger, S., Synthesis and characterisation of mucoadhesive thiolated polymers. Int. J. Pharm. 194 (2000), 239–247.
18. Leitner, V.M., Walker, G.F., Bernkop-Schnürch, A., Thiolated polymers: evidence for the formation of disulphide bonds with mucus glycoproteins. Eur. J. Pharm. Biopharm. 56 (2003), 207–214.
19. Pereira de Sousa, I., Cattoz, B., Wilcox, M.D., Griffiths, P.C., Dalgliesh, R., Rogers, S., Bernkop-Schnürch, A., Nanoparticles decorated with proteolytic enzymes, a promising strategy to overcome the mucus barrier. Eur. J. Pharm. Biopharm. 97 (2015), 257–264.
20. Bernkop-Schnürch, A., Scholler, S., Biebel, R.G., Development of controlled drug release systems based on polymer–cysteine conjugates. J. Control. Release 66 (2000), 39–48.
21. Le-Tien, C., Millette, M., Lacroix, M., Modified alginate matrice for the immobilization of bioactive agents. Biotechnol. Appl. Biochem. 38 (2004), 98–107.
22. Hauptstein, S., Müller, C., Dünnhaupt, S., Laffleur, F., Bernkop-Schnürch, A., Preactivated thiomers: evaluation of gastroretentive minitablets. Int. J. Pharm. 456 (2013), 473–479.
23. Abraham, A., Mihaliuk, E., Kumar, B., Legleiter, J., Gullion, T., Solid-state NMR study of cysteine on gold nanoparticles. J. Phys. Chem. C 114 (2010), 18109–18114.
24. Rahmat, D., Sakloetsakun, D., Shahnaz, G., Perera, G., Kaindl, R., Bernkop-Schnürch, A., Design and synthesis of a novel cationic thiolated polymer. Int. J. Pharm. 411 (2011), 10–17.
25. Kast, C.E., Bernkop-Schnürch, A., Thiolated polymers–thiomers: development and in vitro evaluation of chitosan–thioglycolic acid conjugates. Biomaterials 22 (2001), 2345–2352.
26. Hintzen, F., Hauptstein, S., Perera, G., Bernkop-Schnürch, A., Synthesis and in vitro characterization of entirely S-protected thiolated pectin for drug delivery. Eur. J. Pharm. Biopharm. 85 (2013), 1266–1273.
27. Iqbal, J., Shahnaz, G., Dünnhaupt, S., Müller, C., Hintzen, F., Bernkop-Schnürch, A., Preactivated thiomers as mucoadhesive polymers for drug delivery. Biomaterials 33 (2012), 1528–1535.
28. Carlsson, J., Drevin, H., Axén, R., Protein thiolation and reversible protein–protein conjugation. N-succinimidyl 3-(2-pyridyldithio) propionate, a new heterobifunctional reagent. Biochem. J. 173 (1978), 723–737.
29. Mortazavi, S.A., Smart, J.D., Factors influencing gel-strengthening at the mucoadhesive-mucus interface. J. Pharm. Pharmacol. 46 (1994), 86–90.
30. Smart, J.D., The basics and underlying mechanisms of mucoadhesion. Adv. Drug Deliv. Rev. 57 (2005), 1556–1568.
31. Barthelmes, J., Perera, G., Hombach, J., Dünnhaupt, S., Bernkop-Schnürch, A., Development of a mucoadhesive nanoparticulate drug delivery system for a targeted drug release in the bladder. Int. J. Pharm. 416 (2011), 339–345.
32. Chickering, D.E., Mathiowitz, E., Definitions, mechanisms, and theories of bioadhesion. Mathiowitz, E., Chickering, D.E., Lehr, C.M., (eds.) Bioadhesive drug delivery systems, 1999, Marcel Dekker, New York, 1–10.
33. Duchêne, D., Ponchel, G., Principle and investigation of the bioadhesion mechanism of solid dosage forms. Biomaterials 13 (1992), 709–714.
34. Roldo, M., Hornof, M., Caliceti, P., Bernkop-Schnürch, A., Mucoadhesive thiolated chitosans as platforms for oral controlled drug delivery: synthesis and in vitro evaluation. Eur. J. Pharm. Biopharm. 57 (2004), 115–121.