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01.08.2014 | Original Paper

Preparation and characterization of novel derivatives of chitosan and trimethyl chitosan conjugated with dipeptides and vitamin B12 as candidates for oral delivery of insulin

verfasst von: Nersi Jafary Omid, Niloofar Babanejad, Hossein Amini, Mohsen Amini, Morteza Rafiee Tehrani, Farid Dorkoosh

Erschienen in: Journal of Polymer Research | Ausgabe 8/2014

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Abstract

Chitosan and its derivatives are widely used in drug delivery systems due to their bio-degradebility, bio-compatibility and absorption enhancing properties. Many peptide and protein derived therapeutics cannot be administered through oral rout because of the proteolytic condition of gastro-intestinal tract and their low bio-availability. Insulin is a peptide drug which is widely used in diabetics as repeated daily injection. Due to the fact that there are receptors for didpeptides and vitamine B12 in small intestine, in this research work novel derivatives of chitosan and trimethyl chitosan conjugated with glycyl-glycine, alanyl-alaninie and vitamine B12 were synthesized and characterized. The structure of conjugates as well as substitution of different functional groups was confirmed by different instrumental analytical methods such as Fourier transform infrared, magnetic resonance, and X-ray diffraction spectroscopy. Nano-particles of aforementioned loaded with insulin were prepared and their size, surface electrical charge and morphology characterized and their release profile were studied. The results are promising and reveal that these new chitosan and trimethyl chitosan derivatives are potential vehicles for protein and peptide drug molecules.

Vorheriger Artikel Convenient synthesis and morphology of latex particles composed of poly (methyl methacrylate)-b-poly (n-butyl acrylate) by 1, 1-diphenylethylene (DPE) seeded emulsion polymerization

Nächster Artikel An investigation on shape memory behavior of glass fiber/SBS/LDPE composites

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Guyton AC (1991) Textbook of medical physiology, 8th edn. W. B. Saunders, Philadelphia

Rawn JD (1989) Biochemistry. Carolina Neil Patterson Publishers, Burlington

Cigolle CT, Blaum CS, Halter JB (2009) Diabetes and cardiovascular disease prevention in older adults. Clin Geriatr Med 25(4):607–641. doi:10.1016/j.cger.2009.09.001, vii-viiiCrossRef

Hoeks S, Flu WJ, van Kuijk JP, Bax J, Poldermans D (2009) Cardiovascular risk assessment of the diabetic patient undergoing major noncardiac surgery. Best Pract Res Clin Endocrinol Metab 23(3):361–373. doi:10.1016/j.beem.2009.01.002 CrossRef

Weiss AM (2009) Cardiovascular disease in women. Prim Care 36(1):73–102. doi:10.1016/j.pop.2008.10.012, viiiCrossRef

Lewis SJ (2009) Prevention and treatment of atherosclerosis: a practitioner’s guide for 2008. Am J Med 122(1 Suppl):S38–S50. doi:10.1016/j.amjmed.2008.10.016 CrossRef

Jellinger PS (2007) Metabolic consequences of hyperglycemia and insulin resistance. Clin Cornerstone 8(Supplement 7):S30–S42CrossRef

Conwell LS, Pope E, Artiles AM, Mohanta A, Daneman A, Daneman D (2008) Dermatological complications of continuous subcutaneous insulin infusion in children and adolescents. J Pediatr 152(5):622–628. doi:10.1016/j.jpeds.2007.10.006 CrossRef

Michael G, inventor Emisphere Technologies, Inc., assignee (2008) Night-time oral insulin therapy patent 7,384,914

10.

Hamman JH, Enslin GM, Kotz AF (2005) Oral delivery of peptide drugs. BioDrugs 19(3):165–177CrossRef

11.

Goldberg M, Gomez-Orellana I (2003) Challenges for the oral delivery of macromolecules. Nat Rev Drug Discov 2(4):289–295. doi:10.1038/nrd1067 CrossRef

12.

Morishita M, Peppas NA (2006) Is the oral route possible for peptide and protein drug delivery? Drug Discov Today 11(19–20):905–910. doi:10.1016/j.drudis.2006.08.005 CrossRef

13.

Owens DR, Zinman B, Bolli G (2003) Alternative routes of insulin delivery. Diabet Med 20:886–898CrossRef

14.

Lassmann-Vague V, Raccah D (2006) Alternatives routes of insulin delivery. Diabetes Metab 32:513–522CrossRef

15.

Ekwuribe NN, inventor Protein Delivery, Inc., assignee (1994) Conjugation-stabilized polypeptide compositions, therapeutic delivery and diagnostic formulations comprising same and method of making and using the same patent 5359030

16.

Ekwuribe NN, inventor Protein Delivery, Inc., assignee (1995) Conjugation-stabilized polypeptide compositions, therapeutic delivery and diagnostic formulations comprising same and method of making and using the same patent 5438040

17.

Ekwuribe NN, inventor Protein Deliver, Inc., assignee (1997) Conjugation-stabilized therapeutic agent compositions, delivery and diagnostic formulations comprising same and method of making and using the same patent 5681811

18.

Ekwuribe NN, Ramaswamy M, Radhakrishnan B, Allaudeen HS, inventors; Protein Delivery, Inc., assignee (2001) Hydrophilic and lipophilic balanced microemulsion formulations of free-form and/or conjugated-stabilized therapeutic agents such as insulin patent 6191105

19.

Arbit E, Abbas R, Michael G, Woods TC, Dinh S, Wong V, inventors; Emisphere Technologies, Inc., assignee (2008) Oral insulin therapy patent 7429564

20.

Dorkoosh FA, Coos Verhoef J, Ambagts MHC, Rafiee-Tehrani M, Borchard G, Junginger HE (2002) Peroral delivery systems based on superporous hydrogel polymers: release characteristics for the peptide drugs buserelin, octreotide and insulin. Eur J Pharm Sci 15(5):433–439. doi:10.1016/S0928-0987(02)00028-3 CrossRef

21.

Dorkoosh FA, Verhoef JC, Verheijden JHM, Rafiee-Tehrani M, Borchard G, Junginger HE (2002) Peroral absorption of octreotide in pigs formulated in delivery systems on the basis of superporous hydrogel polymers. Pharm Res 19(10):1532–1536. doi:10.1023/A:1020416918624 CrossRef

22.

Pan Y, Li Y-j, Zhao H-y, Zheng J-m, Xu H, Wei G et al (2002) Bioadhesive polysaccharide in protein delivery system chitosan nanoparticles improve the intestinal absorption of insulin in vivo. Int J Pharm 249:139–147

23.

Sung H-W, Lin Y-H, Tu H, inventors; GP Medical, Inc., assignee (2007) Nanoparticles for protein drug delivery patent 7291598

24.

Hesing-Wen S, Chen M-C, Lin Y-H, Liang H-F, Tu H, inventors; GP Medical, Inc., assignee (2009) Nanoparticles for protein drug delivery patent 7541046

25.

Sung H-W, Liang H-F, Tu H, inventors; GP Medical, Inc., assignee (2009) Nanoparticles for protein drug delivery patent 7604795

26.

Woitiski CB, Neufeld RJ, Veiga F, Carvalho RA, Figueiredo IV (2010) Pharmacological effect of orally delivered insulin facilitated by multilayered stable nanoparticles. Eur J Pharm Sci Off J Eur Fed Pharm Sci 41(3–4):556–563. doi:10.1016/j.ejps.2010.08.009

27.

Avadi MR, Sadeghi AM, Mohammadpour N, Abedin S, Atyabi F, Dinarvand R et al (2010) Preparation and characterization of insulin nanoparticles using chitosan and Arabic gum with ionic gelation method. Nanomedicine: Nanotechnol Biol Med 6(1):58–63. doi:10.1016/j.nano.2009.04.007

28.

Mourya VK, Inamdar NN (2008) Chitosan-modifications and applications: opportunities galore. React Funct Polym 68(6):1013–1051. doi:10.1016/j.reactfunctpolym.2008.03.002 CrossRef

29.

Smith J, Wood E, Dornish M (2004) Effect of chitosan on epithelial cell tight junctions. Pharm Res 21(1):43–49CrossRef

30.

Yin L, Ding J, He C, Cui L, Tang C, Yin C (2009) Drug permeability and mucoadhesion properties of thiolated trimethyl chitosan nanoparticles in oral insulin delivery. Biomaterials 30(29):5691–5700. doi:10.1016/j.biomaterials.2009.06.055 CrossRef

31.

Chalasani KB, Russell-Jones GJ, Jain AK, Diwan PV, Jain SK (2007) Effective oral delivery of insulin in animal models using vitamin B12-coated dextran nanoparticles. J Control Release Off J Control Release Soc 122(2):141–150. doi:10.1016/j.jconrel.2007.05.019 CrossRef

32.

Chalasani KB, Russell-Jones GJ, Yandrapu SK, Diwan PV, Jain SK (2007) A novel vitamin B12-nanosphere conjugate carrier system for peroral delivery of insulin. J Control Rel Off J Control Rel Soc 117(3):421–429. doi:10.1016/j.jconrel.2006.12.003 CrossRef

33.

Russell-Jones GJ, McEwan JF, inventors; Biotech Australia Pty Limited, assignee (2000) Vitamin12 derivatives and methods for their preparation. Australia patent 6150341

34.

Kurita K, Ikeda H, Yoshida Y, Shimojoh M, Harata M (2002) Chemoselective protection of the amino groups of chitosan by controlled phthaloylation: facile preparation of a precursor useful for chemical modifications. Biomacromolecules 3(1):1–4CrossRef

35.

Sahu SK, Mallick SK, Santra S, Maiti TK, Ghosh SK, Pramanik P (2010) In vitro evaluation of folic acid modified carboxymethyl chitosan nanoparticles loaded with doxorubicin for targeted delivery. J Mater Sci Mater Med 21(5):1587–1597. doi:10.1007/s10856-010-3998-4

36.

Sieval AB, Thanou M, Kotzk AF, Verhoef JC, Brussee J, Junginger HE (1998) Preparation and NMR characterization of highly substituted N-trimethyl chitosan chloride.pdf. Carbohydr Polym 36:157–165CrossRef

37.

Li S-Q, Zhou P-J, Yao P-J, Wei Y-A, Zhang Y-H, Yue W (2010) Preparation of O-carboxymethyl-N-trimethyl chitosan chloride and flocculation of the wastewater in sugar refinery. J Appl Polym Sci. doi:10.1002/app.31899

38.

Dash S, Murthy PN, Nath L, Chowdhury P (2010) Kinetic modeling on drug release from controlled drug delivery systems. Acta Pol Pharm-Drug Res 67(3):217–223

39.

Higuchi T, Connors KA (1965) Phase-solubility techniques. Adv Anal Chem Instrum 4:117–122

40.

Korsmyer RW, Gumy R, Doelker E, Buri P, Peppas NA (1983) Mechanisms of solute release from porous hydrophilic polymers. Int J Pharm 15:25–35

41.

Kadajji VG, Betageri GV (2011) Water soluble polymers for pharmaceutical applications. Polymers 3(4):1972–2009CrossRef

42.

Saarinen-Savolainen P, Järvinen T, Taipale H, Urtti A (1997) Method for evaluating drug release from liposomes in sink conditions. Int J Pharm 159(1):27–33

43.

El-Leithy ES, Shaker DS, Ghorab MK, Abdel-Rashid RS (2010) Optimization and characterization of diclofenac sodium microspheres prepared by a modified coacervation method. Drug Discov Ther 4(3):208–216

Titel: Preparation and characterization of novel derivatives of chitosan and trimethyl chitosan conjugated with dipeptides and vitamin B12 as candidates for oral delivery of insulin
verfasst von: Nersi Jafary Omid
Niloofar Babanejad
Hossein Amini
Mohsen Amini
Morteza Rafiee Tehrani
Farid Dorkoosh
Publikationsdatum: 01.08.2014
Verlag: Springer Netherlands
Erschienen in: Journal of Polymer Research / Ausgabe 8/2014
Print ISSN: 1022-9760
Elektronische ISSN: 1572-8935
DOI: https://doi.org/10.1007/s10965-014-0510-8

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