Catechol-Functionalized Succinyl Chitosan for Novel Mucoadhesive Drug Delivery

Nitjawan Sahatsapan; Theerasak Rojanarata; Tanasait  Ngawhirunpat; Praneet Opanasopit; Prasopchai Patrojanasophon

doi:10.4028/www.scientific.net/KEM.819.21

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HomeKey Engineering MaterialsKey Engineering Materials Vol. 819Catechol-Functionalized Succinyl Chitosan for...

Catechol-Functionalized Succinyl Chitosan for Novel Mucoadhesive Drug Delivery

Abstract:

The objective of this research was to synthesized and evaluated a mucoadhesive catechol-bearing succinyl chitosan (Cat-SCS) as an innovative mucoadhesive substance for a mucoadhesive drug delivery system. Succinyl chitosan (SCS) was synthesized via ring-opening reactions with succinic anhydride. The Cat-SCS was then synthesized by reacting SCS with dopamine with the existence of N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDAC) and N-hydroxysulfosuccinimide (NHS). The successful functionalization of catechol onto chitosan backbone was verified using nuclear magnetic resonance spectroscopy (NMR) and Fourier transform infrared spectroscopy (FT-IR). Mucoadhesion studies were performed using rheology measurement and ex-vivo mucoadhesion test. The findings exposed that the synthesized Cat-SCS exhibited excellent mucoadhesive properties which was better than the intact CS. Further indirect studies verified the occurrence of polymer-mucin glycoproteins interactions. The catechol content of catechol moiety on the Cat-SCS was determined to be 0.377 using the ¹H NMR. The cytotoxicity test indicated the biocompatibility of the obtained polymer on human gingival fibroblast cells (HGF cells). Therefore, these results could advocate the capacity to use of Cat-SCS as an innovative mucoadhesive platform for mucoadhesive drug delivery.

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Periodical:

Key Engineering Materials (Volume 819)

Pages:

21-26

DOI:

https://doi.org/10.4028/www.scientific.net/KEM.819.21

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Online since:

August 2019

Authors:

Nitjawan Sahatsapan, Theerasak Rojanarata, Tanasait Ngawhirunpat, Praneet Opanasopit, Prasopchai Patrojanasophon*

Keywords:

Catechol, Chitosan, Dopamine, Mucoadhesive Polymer

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References

[1] M. Rinaudo, Chitin and chitosan, Properties and applications, Progress in Polymer Science. 31, 7 (2006) 603-632.

DOI: 10.1016/j.progpolymsci.2006.06.001

Google Scholar

[2] K. Kim, K. Kim, J.H. Ryu, H. Lee, Chitosan-catechol: A polymer with long-lasting mucoadhesive properties, Biomaterials. 52 (2015) 161-170.

DOI: 10.1016/j.biomaterials.2015.02.010

Google Scholar

[3] A. Bernkop-Schnürch, Thiomers: A new generation of mucoadhesive polymers, Advanced Drug Delivery Reviews. 57, 11 (2005) 1569-1582.

DOI: 10.1016/j.addr.2005.07.002

Google Scholar

[4] M. Davidovich-Pinhas, H. Bianco-Peled, Alginate–PEGAc: A new mucoadhesive polymer, Acta Biomaterialia. 2, 7 (2011) 625-633.

DOI: 10.1016/j.actbio.2010.09.021

Google Scholar

[5] P. Tonglairoum, R.P. Brannigan, P. Opanasopit, V.V. Khutoryanskiy, Maleimide-bearing nanogels as novel mucoadhesive materials for drug delivery, Journal of Materials Chemistry B. 40, 4 (2016) 6581-6587.

DOI: 10.1039/c6tb02124g

Google Scholar

[6] C. Lee, J. Shin, J.S. Lee, E. Byun, J.H. Ryu, S.H. Um, et al., Bioinspired, calcium-free alginate hydrogels with tunable physical and mechanical properties and improved biocompatibility, Biomacromolecules. 14, 6 (2013) 2004-2013.

DOI: 10.1021/bm400352d

Google Scholar

[7] T. Woraphatphadung, W. Sajomsang, P. Gonil, S. Saesoo, P. Opanasopit, Synthesis and characterization of pH-responsive N-naphthyl-N,O-succinyl chitosan micelles for oral meloxicam delivery, Carbohydr Polym. 121 (2015) 99-106.

DOI: 10.1016/j.carbpol.2014.12.039

Google Scholar

[8] N. Sahatsapan, T. Rojanarata, T. Ngawhirunpat, P. Opanasopit, P. Tonglairoum, 6-Maleimidohexanoic acid-grafted chitosan: A new generation mucoadhesive polymer, Carbohydrate Polymers. 202 (2018) 258-264.

DOI: 10.1016/j.carbpol.2018.08.119

Google Scholar

[9] E.E. Hassan, J.M. Gallo, A simple rheological method for the in vitro assessment of mucin-polymer bioadhesive bond strength. Pharmaceutical Research. 7, 5 (1990) 491-495.

Google Scholar

[10] S. Rossi, F. Ferrari, M. C. Bonferoni, C. Caramella, Characterization of chitosan hydrochloride–mucin rheological interaction: influence of polymer concentration and polymer: mucin weight ratio. European Journal of Pharmaceutical Sciences, 12, 4 (2001) 479–485.

DOI: 10.1016/s0928-0987(00)00194-9

Google Scholar

[11] P. Sriamornsak, N. Wattanakorn, Rheological synergy in aqueous mixtures of pectin and mucin. Carbohydrate Polymers, 74 (2008) 474–481.

DOI: 10.1016/j.carbpol.2008.03.021

Google Scholar

[12] S. Moulay, Hydrogels from Catechol-Conjugated Polymeric Materials. in: V.K. Thakur, M.K. Thakur, (Eds.) Hydrogels: Recent Advances, Springer Singapore, Singapore, 2018, pp.435-470.

DOI: 10.1007/978-981-10-6077-9_16

Google Scholar

[13] T. Li, S. Takeoka, A novel application of maleimide for advanced drug delivery: in vitro and in vivo evaluation of maleimide-modified pH-sensitive liposomes, Int J Nanomedicine. 8 (2013) 3855-3866.

DOI: 10.2147/ijn.s47749

Google Scholar