Effect of the copolymerized aromatic and unsaturated monomers on the affinity of drug-polyesters in the core-shell nanoparticles

Salman Hassanzadeh; Sepideh Khoee; Loghman Firoozpour

Macromolecular Research, Vol.21, No.1, 55-64, January, 2013

DOI10.1007/s13233-013-1004-y Export Citation

Effect of the copolymerized aromatic and unsaturated monomers on the affinity of drug-polyesters in the core-shell nanoparticles

Salman Hassanzadeh^†, Sepideh Khoee, and Loghman Firoozpour¹

Polymer Chemistry Department, School of Science, University of Tehran, Tehran, P.O. Box 14155-6455, Iran
¹Medicinal Chemistry Department, Faculty of pharmacy, Tehran University of medical sciences, Tehran, P.O. Box 14155-6451, Iran

E-mail:

The objective of this study was to get an insight into the influence of the newly provided functional groups from the copolymerization as a strategy on the total interactions of the hydrophobic drug and the polyesteric core of the prepared core-shell nanoparticles. Three amphiphile triblock models of monomethoxy poly(ethylene gycol) (mPEG)-b-polyester-b-mPEG with the same PEG hydrophile part but different hydrophobe polyesteric segments were synthesized and used for preparation of the core-shell nanoparticles that were loaded by quercetin as a model hydrophobe drug in the core. The total amount of the interaction between polyesters in the core and loaded quercetin were monitored by parameters such as drug loadings, in vitro release rates and other newly defined parameters such as micelle encapsulation efficiency. The results highlighted that changing the structure of the saturated aliphatic polyesteric core in the poly(butylene adipate) with diol monomers that are capable of forming additional π stacking and π -OH interactions with quercetin weakens the optimal conditions for the main drug-esteric hydrogen bonding. Therefore, the decreased total affinity of the quercetin and polyesteric core finally resulted in the lower amount of encapsulated drug and the increased release rate.

Keywords:core shell nanoparticles;drug-core forming polymer interactions;copolymerization;drug loading;release models

[References]

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[1] Jain R, Shah NH, Malick AW, Rhodes CT, Drug Dev. Ind. Pharm., 24, 703 (1998)

[2] Deshpande AA, Heller J, Crit. Rev. Ther. Drug Carrier Syst., 15, 381 (1998)

[3] Duncan R, Nat. Rev. Drug Discov., 2, 347 (2003)

[4] Kopecek J, Biomaterials., 28, 5185 (2007)

[5] Ikada Y, Tsuji H, Macromol. Rapid Commun., 21(3), 117 (2000)

[6] Andersson L, Davies J, Duncan R, Ferruti P, Ford J, Kneller S, Mendichi R, Pasut G, Schiavon O, Summerford C, Tirk A, Veronese FM, Vincenzi V, Wu GF, Biomacromolecules, 6(2), 914 (2005)

[7] Hans ML, Lowman AM, Curr. Opin. Solid State Mater. Sci., 6, 319 (2002)

[8] Otsuka H, Nagasaki Y, Kataoka K, Adv. Drug Deliv. Rev., 55, 403 (2003)

[9] Lavasanifar A, Samuel J, Kwon GS, Adv. Drug Deliv.Rev., 54, 169 (2002)

[10] Kim JH, Nagasaki Y, Kataoka K, J. Ind. Eng. Chem., 4(3), 244 (1998)

[11] Jain RA, Biomaterials., 21, 2475 (2000)

[12] Jerome C, Lecomte P, Adv. Drug Deliv. Rev., 60, 1056 (2008)

[13] Kataoka K, Harada A, Nagasaki Y, Adv. Drug Deliv. Rev., 47, 113 (2001)

[14] Lin JP, Zhang SN, Chen T, Lin SL, Jin HT, Int. J.Pharm., 336, 49 (2007)

[15] Nguyen A, Marsaud V, Bouclier C, Top C, Vessieres A, Pigeon P, Gref R, Legrand P, Jaouen G, Renoir JM, Int.J. Pharm., 347, 128 (2008)

[16] Huang M, Wu W, Qian J, Wan DJ, Wei XL, Zhu JH, Acta Pharmacol. Sinica., 26, 1512 (2005)

[17] Allen C, Maysinger D, Eisenberg A, Colloids Surf. B:Biointerfaces., 16, 3 (1999)

[18] Khoee S, Hassanzadeh S, Goliaie B, Nanotechnology., 18, 175602 (2007)

[19] Kaplan IG, Intermolecular Interactions: Physical Picture, Computational Methods and Model Potentials, John Wiley & Sons Ltd., Chichaster (2005)

[20] Rademacher P, Khelashvili L, Kowski K, Org. Biomol. Chem., 3, 2620 (2005)

[21] McGaughey GB, Gagne M, Rappe AK, J. Biol. Chem., 273, 15458 (1998)

[22] Masayuki Y, Mizue M, Noriko Y, Teruo O, Yasuhisa S, Kazunori K, Shohei I, J. Control. Release., 11, 269 (1990)

[23] Fessi H, Puisieux F, Devissaguet JP, Ammoury N, Benita S, Int. J. Pharm., 55, R1 (1989)

[24] Bilati U, Allemann E, Doelker E, Eur. J. Pharm. Sci., 24, 67 (2005)

[25] Devanand K, Selser JC, Macromolecules., 24, 5943 (1991)

[26] d'Acunzo F, Le TQ, Kohn J, Macromolecules, 35(25), 9366 (2002)

[27] Marangoni DG, Rodenhiser AP, Thomas JM, Kwak JCT, Langmuir., 9, 438 (1993)

[28] Jeong YI, Cheon JB, Kim SH, Nah JW, Lee YM, Sung YK, Akaike T, Cho CS, J. Control. Release., 51, 169 (1998)

[29] Nishiyama N, Kataoka K, in Polymer Therapeutics Ii: Polymers as Drugs, Conjugates and Gene Delivery Systems, Springer, Berlin, 193, 67 (2006)

[30] Morokuma K, Accounts of Chemical Research., 10, 294 (1977)

[31] Cambon A, Alatorre-Meda M, Juarez J, Topete A, Mistry D, Attwood D, Barbosa S, Taboada P, Mosquera V, J. Colloid Interface Sci., 361(1), 154 (2011)