Thiomers and thiomer-based nanoparticles in protein and DNA drug delivery

Bibliography

• Werle M, Bernkop-Schnurch A. Thiolated chitosans: useful excipients for oral drug delivery. J Pharm Pharmacol 2008;60(3):273-81
   PubMed Web of Science ®Google Scholar
• Khafagy E-S, Morishita M, Onuki Y, Takayama K. Current challenges in non-invasive insulin delivery systems: a comparative review. Adv Drug Deliv Rev 2007;59(15):1521-46
   PubMed Web of Science ®Google Scholar
• Antosova Z, Mackova M, Kral V, Macek T. Therapeutic application of peptides and proteins: parenteral forever? Trends Biotechnol 2009;27(11):628-35
   PubMed Web of Science ®Google Scholar
• Frokjaer S, Otzen DE. Protein drug stability: a formulation challenge. Nat Rev Drug Discov 2005;4(4):298-306
   PubMed Web of Science ®Google Scholar
• Emerich DF, Thanos CG. The pinpoint promise of nanoparticle-based drug delivery and molecular diagnosis. Biomol Eng 2006;23(4):171-84
   PubMedGoogle Scholar
• Hobbs SK, Monsky WL, Yuan F, Regulation of transport pathways in tumor vessels: role of tumor type and microenvironment. Proc Natl Acad Sci USA 1998;95(8):4607-12
   PubMed Web of Science ®Google Scholar
• Yih TC, Al-Fandi M. Engineered nanoparticles as precise drug delivery systems. J Cell Biochem 2006;97(6):1184-90
   PubMed Web of Science ®Google Scholar
• des Rieux A, Fievez V, Garinot M, Nanoparticles as potential oral delivery systems of proteins and vaccines: a mechanistic approach. J Control Release 2006;116(1):1-27
   PubMed Web of Science ®Google Scholar
• Chaudhury A, Das S. Recent advancement of chitosan-based nanoparticles for oral controlled delivery of insulin and other therapeutic agents. AAPS PharmSciTech 2011;12(1):10-20
   PubMed Web of Science ®Google Scholar
• Makhlof A, Tozuka Y, Takeuchi H. Design and evaluation of novel pH-sensitive chitosan nanoparticles for oral insulin delivery. Eur J Pharm Sci 2011;42(5):445-51
   PubMed Web of Science ®Google Scholar
• Grabovac V, Guggi D, Bernkop-Schnurch A. Comparison of the mucoadhesive properties of various polymers. Adv Drug Deliv Rev 2005;57(11):1713-23
   PubMed Web of Science ®Google Scholar
• Hornof MD, Bernkop-Schnurch A. In vitro evaluation of the permeation enhancing effect of polycarbophil-cysteine conjugates on the cornea of rabbits. J Pharm Sci 2002;91(12):2588-92
   PubMed Web of Science ®Google Scholar
• Kast CE, Guggi D, Langoth N, Bernkop-Schnurch A. Development and in vivo evaluation of an oral delivery system for low molecular weight heparin based on thiolated polycarbophil. Pharm Res 2003;20(6):931-6
   PubMed Web of Science ®Google Scholar
• Takeuchi H, Yamamoto H, Kawashima Y. Mucoadhesive nanoparticulate systems for peptide drug delivery. Adv Drug Deliv Rev 2001;47(1):39-54
   PubMed Web of Science ®Google Scholar
• Werle M, Hoffer M. Glutathione and thiolated chitosan inhibit multidrug resistance P-glycoprotein activity in excised small intestine. J Control Release 2006;111(1-2):41-6
   PubMed Web of Science ®Google Scholar
• Foger F, Schmitz T, Bernkop-Schnurch A. In vivo evaluation of an oral delivery system for P-gp substrates based on thiolated chitosan. Biomaterials 2006;27(23):4250-5
   PubMed Web of Science ®Google Scholar
• Albrecht K, Bernkop-Schnurch A. Thiomers: forms, functions and applications to nanomedicine. Nanomedicine (Lond) 2007;2(1):41-50
   PubMed Web of Science ®Google Scholar
• Bernkop-Schnurch A, Hornof M, Zoidl T. Thiolated polymers–thiomers: synthesis and in vitro evaluation of chitosan-2-iminothiolane conjugates. Int J Pharm 2003;260(2):229-37
   PubMed Web of Science ®Google Scholar
• Kafedjiiski K, Krauland AH, Hoffer MH, Bernkop-Schnurch A. Synthesis and in vitro evaluation of a novel thiolated chitosan. Biomaterials 2005;26(7):819-26
   PubMed Web of Science ®Google Scholar
• Millotti G, Samberger C, Frohlich E, Bernkop-Schnurch A. Chitosan-graft-6-mercaptonicotinic acid: synthesis, characterization, and biocompatibility. Biomacromolecules 2009;10(11):3023-7
   PubMed Web of Science ®Google Scholar
• Bernkop-Schnurch A, Hoffer MH, Kafedjiiski K. Thiomers for oral delivery of hydrophilic macromolecular drugs. Expert Opin Drug Deliv 2004;1(1):87-98
   PubMedGoogle Scholar
• Rahmat D, Sakloetsakun D, Shahnaz G, Design and synthesis of a novel cationic thiolated polymer. Int J Pharm 2011;411(1-2):10-17
   PubMed Web of Science ®Google Scholar
• Bernkop-Schnurch A. Thiomers: a new generation of mucoadhesive polymers. Adv Drug Deliv Rev 2005;57(11):1569-82
   PubMed Web of Science ®Google Scholar
• Bernkop-Schnurch A, Schwarz V, Steininger S. Polymers with thiol groups: a new generation of mucoadhesive polymers? Pharm Res 1999;16(6):876-81
   PubMed Web of Science ®Google Scholar
• Bernkop-Schnurch A, Clausen AE, Hnatyszyn M. Thiolated polymers: synthesis and in vitro evaluation of polymer-cysteamine conjugates. Int J Pharm 2001;226(1-2):185-94
   PubMed Web of Science ®Google Scholar
• Bernkop-Schnurch A, Leitner V, Moser V. Synthesis and in vitro characterization of a poly(acrylic acid)-homocysteine conjugate. Drug Dev Ind Pharm 2004;30(1):1-8
   PubMed Web of Science ®Google Scholar
• Bernkop-Schnurch A, Kast CE, Richter MF. Improvement in the mucoadhesive properties of alginate by the covalent attachment of cysteine. J Control Release 2001;71(3):277-85
   PubMed Web of Science ®Google Scholar
• Bernkop-Schnurch A, Steininger S. Synthesis and characterisation of mucoadhesive thiolated polymers. Int J Pharm 2000;194(2):239-47
   PubMed Web of Science ®Google Scholar
• Majzoob S, Atyabi F, Dorkoosh F, Pectin-cysteine conjugate: synthesis and in-vitro evaluation of its potential for drug delivery. J Pharm Pharmacol 2006;58(12):1601-10
   PubMed Web of Science ®Google Scholar
• Jindal AB, Wasnik MN, Nair HA. Synthesis of thiolated alginate and evaluation of mucoadhesiveness, cytotoxicity and release retardant properties. Indian J Pharm Sci 2010;72(6):766-74
   PubMed Web of Science ®Google Scholar
• 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(1):38-44
   PubMed Web of Science ®Google Scholar
• Sharma R, Ahuja M, Kaur H. Thiolated pectin nanoparticles: preparation, characterization and ex vivo corneal permeation study. Carbohydr Polym 2011;87:1606-10
   Web of Science ®Google Scholar
• Brandt J, Svenson A, Carlsson J, Drevin H. Covalent coupling of unsaturated compounds to thiol agrarose using gamma-Radiation. A new method for preparation of adsorbents for affinity chromatography. Appl Biochem Biotechnol 1977(2):2:109
   Google Scholar
• Marschutz MK, Bernkop-Schnurch A. Thiolated polymers: self-crosslinking properties of thiolated 450 kDa poly(acrylic acid) and their influence on mucoadhesion. Eur J Pharm Sci 2002;15(4):387-94
   PubMed Web of Science ®Google Scholar
• Burner U, Jantschko W, Obinger C. Kinetics of oxidation of aliphatic and aromatic thiols by myeloperoxidase compounds I and II. FEBS Lett 1999;443(3):290-6
   PubMed Web of Science ®Google Scholar
• Mueller Christiane, Verroken Andrea, Iqbal Javed, Bernkop-Schnuerch Andreas. Journal of Applied Polymer Science, 2012; 124(6):5046?5055
   Google Scholar
• Millotti G, Samberger C, Frohlich E, Chitosan-4-mercaptobenzoic acid: synthesis and characterization of a novel thiolated chitosan. J Mater Chem 2010;20(12):2432-40
   Web of Science ®Google Scholar
• Perera G, Hombach J, Bernkop-Schnurch A. Hydrophobic thiolation of pectin with 4-aminothiophenol: synthesis and in vitro characterization. AAPS PharmSciTech 2010;11(1):174-80
   PubMed Web of Science ®Google Scholar
• Carlsson J, Drevin H, Axen R. Protein thiolation and reversible protein-protein conjugation. N-Succinimidyl 3-(2-pyridyldithio)propionate, a new heterobifunctional reagent. Biochem J 1978;173(3):723-37
   PubMed Web of Science ®Google Scholar
• Norris R, Brocklehurst K. A convenient method of preparation of high-activity urease from Canavalia ensiformis by covalent chromatography and an investigation of its thiol groups with 2,2′-dipyridyl disulphide as a thiol titrant and reactivity probe. Biochem J 1976;159(2):245-57
   PubMed Web of Science ®Google Scholar
• Iqbal J, Shahnaz G, Dunnhaupt S, Preactivated thiomers as mucoadhesive polymers for drug delivery. Biomaterials 2012;33(5):1528-35
   PubMed Web of Science ®Google Scholar
• Forrest HS, Fuller AT, Walker J. Chemotherapeutic agents of the sulphone type; effect of homologation on the antibacterial activity of p-methylsulphonyl-benzamidine and p-methylsulphonyl-benzylamine hydrochlorides. J Chem Soc 1948;3:1501-6
   PubMed Web of Science ®Google Scholar
• Dunnhaupt S, Barthelmes J, Rahmat D, S-protected thiolated chitosan for oral delivery of hydrophilic macromolecules: evaluation of permeation enhancing and efflux pump inhibitory properties. Mol Pharm 2012;9(5):1331-41
   PubMed Web of Science ®Google Scholar
• Smart JD. The basics and underlying mechanisms of mucoadhesion. Adv Drug Deliv Rev 2005;57(11):1556-68
   PubMed Web of Science ®Google Scholar
• Bernkop-Schnurch A, Hornof M, Guggi D. Thiolated chitosans. Eur J Pharm Biopharm 2004;57(1):9-17
   PubMed Web of Science ®Google Scholar
• Kast CE, Bernkop-Schnurch A. Thiolated polymers–thiomers: development and in vitro evaluation of chitosan-thioglycolic acid conjugates. Biomaterials 2001;22(17):2345-52
   PubMed Web of Science ®Google Scholar
• Hombach J, Bernkop-Schnurch A. Mucoadhesive drug delivery systems. Handb Exp Pharmacol 2010(197):251-66
   PubMedGoogle Scholar
• Dunnhaupt S, Barthelmes J, Hombach J, Distribution of thiolated mucoadhesive nanoparticles on intestinal mucosa. Int J Pharm 2011;408(1-2):191-9
   PubMed Web of Science ®Google Scholar
• Barthelmes J, Perera G, Hombach J, Development of a mucoadhesive nanoparticulate drug delivery system for a targeted drug release in the bladder. Int J Pharm 2011;416(1):339-45
   PubMed Web of Science ®Google Scholar
• Barthelmes J, Dunnhaupt S, Unterhofer S, Thiolated particles as effective intravestical drug delivery system for treatment of bladder related diseases. 2012; Under revision
   Google Scholar
• Aungst BJ. Absorption enhancers: applications and advances. The AAPS Journal 2012;14(1):10-18
   PubMed Web of Science ®Google Scholar
• Luessen HL, de Leeuw BJ, Langemeyer MW, Mucoadhesive polymers in peroral peptide drug delivery. VI. Carbomer and chitosan improve the intestinal absorption of the peptide drug buserelin in vivo. Pharm Res 1996;13(11):1668-72
   PubMed Web of Science ®Google Scholar
• Werle M, Kafedjiiski K, Kolmar H, Bernkop-Schnurch A. Evaluation and improvement of the properties of the novel cystine-knot microprotein McoEeTI for oral administration. Int J Pharm 2007;332(1-2):72-9
   PubMed Web of Science ®Google Scholar
• Bernkop-Schnurch A, Guggi D, Pinter Y. Thiolated chitosans: development and in vitro evaluation of a mucoadhesive, permeation enhancing oral drug delivery system. J Control Release 2004;94(1):177-86
   PubMed Web of Science ®Google Scholar
• Clausen AE, Kast CE, Bernkop-Schnurch A. The role of glutathione in the permeation enhancing effect of thiolated polymers. Pharm Res 2002;19(5):602-8
   PubMed Web of Science ®Google Scholar
• Grafstrom R, Stead AH, Orrenius S. Metabolism of extracellular glutathione in rat small-intestinal mucosa. Eur J Biochem 1980;106(2):571-7
   PubMedGoogle Scholar
• Staddon JM, Herrenknecht K, Smales C, Rubin LL. Evidence that tyrosine phosphorylation may increase tight junction permeability. J Cell Sci 1995;108(Pt 2):609-19
   PubMed Web of Science ®Google Scholar
• Wang X, Iqbal J, Rahmat D, Bernkop-Schnurch A. Preaktivated thiomers: permeation enhancing properties. In preparation
   Google Scholar
• Silverman JA. Multidrug-resistance transporters. Pharm Biotechnol 1999;12:353-86
   PubMedGoogle Scholar
• Varma MV, Ashokraj Y, Dey CS, Panchagnula R. P-glycoprotein inhibitors and their screening: a perspective from bioavailability enhancement. Pharmacol Res 2003;48(4):347-59
   PubMed Web of Science ®Google Scholar
• Dunnhaupt S, Barthelmes J, Rahmat D, S-protected thiolated chitosan for oral delivery of hydrophilic macromolecules: evaluation of permeation enhancing and efflux pump inhibitory properties. Mol Pharmaceutics 2012;9(5):pp 1331-1341
   Web of Science ®Google Scholar
• Amidi M, Mastrobattista E, Jiskoot W, Hennink WE. Chitosan-based delivery systems for protein therapeutics and antigens. Adv Drug Deliv Rev 2010;62(1):59-82
   PubMed Web of Science ®Google Scholar
• Millotti G, Perera G, Vigl C, The use of chitosan-6-mercaptonicotinic acid nanoparticles for oral peptide drug delivery. Drug Deliv 2011;18(3):190-7
   PubMed Web of Science ®Google Scholar
• Sakloetsakun D, Perera G, Hombach J, The impact of vehicles on the mucoadhesive properties of orally administrated nanoparticles: a case study with chitosan-4-thiobutylamidine conjugate. AAPS PharmSciTech 2010;11(3):1185-92
   PubMed Web of Science ®Google Scholar
• Bernkop-Schnurch A, Heinrich A, Greimel A. Development of a novel method for the preparation of submicron particles based on thiolated chitosan. Eur J Pharm Biopharm 2006;63(2):166-72
   PubMed Web of Science ®Google Scholar
• Barthelmes J, Dunnhaupt S, Hombach J, Bernkop-Schnurch A. Thiomer nanoparticles: stabilization via covalent cross-linking. Drug Deliv 2011;18(8):613-19
   PubMed Web of Science ®Google Scholar
• Thaurer MH, Deutel B, Schlocker W, Bernkop-Schnurch A. Development of nanoparticulate drug delivery systems based on thiolated poly(acrylic acid). J Microencapsul 2009;26(3):187-94
   PubMed Web of Science ®Google Scholar
• Bravo-Osuna I, Schmitz T, Bernkop-Schnurch A, Elaboration and characterization of thiolated chitosan-coated acrylic nanoparticles. Int J Pharm 2006;316(1-2):170-5
   PubMed Web of Science ®Google Scholar
• Mazzaferro S, Bouchemal K, Vauthier C, What are parameters affecting Leu-enkephalin loading and release from poly(isobutylcyanoacrylate) nanoparticles coated with thiolated chitosan? J Drug Deliv Sci Technol 2011;21(5):385-93
   Web of Science ®Google Scholar
• Nagpal K, Singh SK, Mishra DN. Chitosan nanoparticles: a promising system in novel drug delivery. Chem Pharm Bull (Tokyo) 2010;58(11):1423-30
   PubMed Web of Science ®Google Scholar
• Saboktakin MR, Tabatabaie RM, Maharramov A, Ramazanov MA. Synthesis and in vitro evaluation of thiolated chitosan-dextran sulfate nanoparticles for the delivery of letrozole. 2010;1(2):62-7
   Google Scholar
• Agnihotri SA, Mallikarjuna NN, Aminabhavi TM. Recent advances on chitosan-based micro- and nanoparticles in drug delivery. J Control Release 2004;100(1):5-28
   PubMed Web of Science ®Google Scholar
• Lee D, Zhang W, Shirley SA, Thiolated chitosan/DNA nanocomplexes exhibit enhanced and sustained gene delivery. Pharm Res 2007;24(1):157-67
   PubMed Web of Science ®Google Scholar
• Yin L, Ding J, He C, Drug permeability and mucoadhesion properties of thiolated trimethyl chitosan nanoparticles in oral insulin delivery. Biomaterials 2009;30(29):5691-700
   PubMed Web of Science ®Google Scholar
• Perera G, Greindl M, Palmberger TF, Bernkop-Schnurch A. Insulin-loaded poly(acrylic acid)-cysteine nanoparticles: stability studies towards digestive enzymes of the intestine. Drug Deliv 2009;16(5):254-60
   PubMed Web of Science ®Google Scholar
• Bouchemal K, Ponchell G, Mazzaferro S, A new approach to determine loading efficiency of Leu-enkephalin in poly(isobutylcyanoacrylate) nanoparticles coated with thiolated chitosan. J Drug Deliv Sci Technol 2008;18(6):392-7
   Web of Science ®Google Scholar
• Requena V, Bouchemal K, Vauthier C, Ponchel G. Encapsulation of leu-enkephalin in core-shell isobutylcyanoacrylate - thiolated chitosan nanoparticles for oral administratton. J Chilean Chem Soc 2008;53(4):1677-81
   Web of Science ®Google Scholar
• Shahnaz G, Vetter A, Barthelmes J, Thiolated chitosan nanoparticles for the nasal administration of leuprolide: bioavailability and pharmacokinetic characterization. Int J Pharm 2012;428(1-2):164-70
   PubMed Web of Science ®Google Scholar
• Makhlof A, Werle M, Tozuka Y, Takeuchi H. Nanoparticles of glycol chitosan and its thiolated derivative significantly improved the pulmonary delivery of calcitonin. Int J Pharm 2010;397(1-2):92-5
   PubMed Web of Science ®Google Scholar
• Carlisle RC, Etrych T, Briggs SS, Polymer-coated polyethylenimine/DNA complexes designed for triggered activation by intracellular reduction. J Gene Med 2004;6(3):337-44
   PubMed Web of Science ®Google Scholar
• Kommareddy S, Amiji M. Preparation and evaluation of thiol-modified gelatin nanoparticles for intracellular DNA delivery in response to glutathione. Bioconjug Chem 2005;16(6):1423-32
   PubMed Web of Science ®Google Scholar
• Mao HQ, Roy K, Troung-Le VL, Chitosan-DNA nanoparticles as gene carriers: synthesis, characterization and transfection efficiency. J Control Release 2001;70(3):399-421
   PubMed Web of Science ®Google Scholar
• Talaei F, Azizi E, Dinarvand R, Atyabi F. Thiolated chitosan nanoparticles as a delivery system for antisense therapy: evaluation against EGFR in T47D breast cancer cells. Int J Nanomedicine 2011;6:1963-75
   PubMed Web of Science ®Google Scholar
• Martien R, Loretz B, Thaler M, Chitosan-thioglycolic acid conjugate: an alternative carrier for oral nonviral gene delivery? J Biomed Mater Res A 2007;82(1):1-9
   PubMed Web of Science ®Google Scholar
• Counis MF, Torriglia A. DNases and apoptosis. Biochem Cell Biol 2000;78(4):405-14
   PubMed Web of Science ®Google Scholar
• Schmitz T, Bravo-Osuna I, Vauthier C, Development and in vitro evaluation of a thiomer-based nanoparticulate gene delivery system. Biomaterials 2007;28(3):524-31
   PubMed Web of Science ®Google Scholar
• Loretz B, Thaler M, Bernkop-Schnurch A. Role of sulfhydryl groups in transfection? A case study with chitosan-NAC nanoparticles. Bioconjug Chem 2007;18(4):1028-35
   PubMed Web of Science ®Google Scholar