Abstract
A new pH-responsive polymer (TKP–AA–PAA) was synthesized from the combination of tamarind kernel powder (TKP), acrylic acid (AA), and polyamidoamine (PAA) which was utilized for controlled release of 5-aminosalicylic acid (5-ASA) in buffer medium. The network structure of TKP–AA–PAA was obtained by irradiating the mixture of TKP, AA, and PAA in different proportion in presence of 2,2-dimethoxy-2-phenyl acetophenone as a photoinitiator. The dynamic and equilibrium swelling properties of the polymeric materials were studied as a function of pH and time in different buffer solutions similar to that of gastric and intestinal fluids. The controlled release kinetics of 5-ASA in simulated body fluid showed a Fickian diffusion behavior.
Similar content being viewed by others
References
Langer R, Peppas NA (2003) Advances in biomaterials, drug delivery, and bionanotechnology. AIChE J 49:2990–3006
Sokolsky-Papkov M, Agashi K, Olaye A, Shakesheff K, Domb AJ (2007) Polymer carriers for drug delivery in tissue engineering. Adv Drug Deliv Rev 59:187–206
Devine DM, Higginbotham CL (2005) Synthesis and characterisation of chemically crosslinked N-vinyl pyrrolidinone (NVP) based hydrogels. Eur Polym J 41:1272–1279
Choi KY, Lee S, Park K, Kim K, Park JH, Kwon IC, Jeong SY (2008) Preparation and characterization of hyaluronic acid-based hydrogel nanoparticles. J Phys Chem Solids 69:1591–1595
Dayananda K, He C, Park DK, Park TG, Lee DS (2008) pH- and temperature-sensitive multiblock copolymer hydrogels composed of poly(ethylene glycol) and poly(amino urethane). Polymer 49:4968–4973
García DM, Escobar JL, Noa Y, Bada N, Hernáez E, Katime I (2004) Timolol maleate release from pH-sensible poly(2-hydroxyethyl methacrylate-co-methacrylic acid) hydrogels. Eur Polym J 40:1683–1690
Tanaka Y, Gong JP, Osada Y (2005) Novel hydrogels with excellent mechanical performance. Prog Polym Sci 30:1–9
Sun JX, Luo YF, Peng H, Han ZW (2008) Design, synthesis and characterization of a novel pH-sensitive hydrogel. Chin Chem Lett 19:1475–1478
Kost J, Langer R (2001) Responsive polymeric delivery systems. Adv Drug Deliv Rev 46:125–148
Coviello T, Palleschi A, Grassi M, Matricardi P, Bocchinfuso G, Alhaique F (2005) Scleroglucan: a versatile polysaccharide for modified drug delivery. Molecules 10:6–33
Francis Suh J-K, Matthew HWT (2000) Application of chitosan-based polysaccharide biomaterials in cartilage tissue engineering: a review. Biomaterials 21:2589–2598
Xiao C, Li H, Gao Y (2009) Preparation of fast pH-responsive ferric carboxymethylcellulose/poly(vinyl alcohol) double-network microparticles. Polym Int 58:112–115
Ferruti P, Marchisio MA, Duncan R (2002) Poly(amido-amine)s: biomedical applications. Macromol Rapid Commun 23:332–355
Bignotti F, Sozzani P, Ranucci E, Ferruti P (1994) NMR studies, molecular characterization, and degradation behavior of poly(amido amine)s. 1. Poly(amido amine) deriving from the polyaddition of 2-methylpiperazine to 1,4-bis(acryloyl)piperazine. Macromolecules 27:7171–7178
Ferruti P, Manzoni S, Richardson SCW, Duncan R, Pattrick NG, Mendichi R, Casolaro M (2000) Amphoteric linear poly(amido-amine)s as endosomolytic polymers: correlation between physicochemical and biological properties. Macromolecules 33:7793–7800
Kosmala JD, Henthorn DB, Brannon-Peppas L (2000) Preparation of interpenetrating networks of gelatin and dextran as degradable biomaterials. Biomaterials 21:2019–2023
Richardson SCW, Pattrick NG, Man YKS, Ferruti P, Duncan R (2001) Poly(amidoamine)s as potential nonviral vectors: ability to form interpolyelectrolyte complexes and to mediate transfection in vitro. Biomacromolecules 2:1023–1028
Pattrick NG, Richardson SCW, Casolaro M, Ferruti P, Duncan R (2001) Poly(amidoamine)-mediated intracytoplasmic delivery of ricin A-chain and gelonin. J Control Release 77:225–232
Tanzi MC, Levi M (1989) Heparinizable segmented polyurethanes containing poly-amidoamine blocks. J Biomed Mater Res 23:863–881
Wiwattanapatape R, Lomlim L, Saramunee K (2003) Dendrimers conjugates for colonic delivery of 5-aminosalicylic acid. J Control Release 88:1–9
Nakanishi K (1966) Infrared absorption spectroscopy practical, 4th edn. Nankodo Company Ltd., Tokyo, pp 142–143
Borzacchiello A, Ambrosio L, Netti PA, Nicolais L, Peniche C, Gallardo A, Roman SJ (2001) Chitosan-based hydrogels: synthesis and characterization. J Mater Sci Mater Med 12:861–864
Xue W, Champ S, Huglin MB, Jones TGJ (2004) Rapid swelling and deswelling in cryogels of crosslinked poly(N-isopropylacrylamide-co-acrylic acid. Eur Polym J 40:467–476
Qiu Y, Park K (2001) Environment-sensitive hydrogels for drug delivery. Adv Drug Deliv Rev 53:321–339
Firestone BA, Siegel RA (1991) Kinetics and mechanisms of water sorption in hydrophobic, ionizable copolymer gels. J Appl Polym Sci 43:901–914
Kim B, Flamme KL, Peppas NA (2003) Dynamic swelling behavior of pH-sensitive anionic hydrogels used for protein delivery. J Appl Polym Sci 89:1606–1613
Brannon-Peppas L, Peppas NA (1990) Dynamic and equilibrium swelling behaviour of pH-sensitive hydrogels containing 2-hydroxyethyl methacrylate. Biomaterials 11:635–644
Ghandehari H, Kopeckova P, Kopecek J (1997) In vitro degradation of pH-sensitive hydrogels containing aromatic azo bonds. Biomaterials 18:861–872
Bajpai SK, Tankhiwale R (2006) Investigation of dynamic release of vitamin B2 from calcium alginate/chitosan multilayered beads: part II. React Funct Polym 66:1565–1574
Acknowledgment
R.K.D. is thankful to Professor A. R. Ray for useful discussions. Kind help of CIF, BIT, Mesra, is thankfully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Dey, R.K., Tiwary, G.S., Patnaik, T. et al. Controlled release of 5-aminosalicylic acid from a new pH responsive polymer derived from tamarind seed polysaccharide, acrylic acid, and polyamidoamine. Polym. Bull. 66, 583–598 (2011). https://doi.org/10.1007/s00289-010-0294-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-010-0294-x