Abstract
In this work, new class of supramolecular copolydendrimers (SCDs) consisting of polyamidoamines (PAMAMs) and polyglycerol were synthesized through host-guest interactions. SCDs were able to encapsulate, transport, and release doxorubicin (DOX) efficiently. Host-guest interactions between PAMAM and polyglycerol was depended on pH so that aqueous solutions of SCDs and SCDs-based drug delivery systems were stable at room temperature and pH = 7.4, but their building blocks were separated in lower pHs(<pH = 5.5). This property was used for controlled release of DOX molecules from SCDs. Loading capacity of SCDs was depended on the generation of PAMAM and also number of attached polyglycerols on its periphery. According to spectroscopy and microscopy evaluations, size of SCDs and SCDs-based drug delivery systems was 114 and 129 nm, respectively. Due to their own fluorescence, drug delivery systems could be studied either by following encapsulated DOX molecules or SCDs.
References
Lehn JM (1995) Supramolecular chemistry: concepts and perspectives; VCH: Weinheim, Germany. Chapter 9:139–197
Brunsveld L, Folmer BJB, Meijer EW, Sijbesma RP (2001) Supramolecular polymers. Chem Rev 101(12):4071–4097
Harada A (2006) Supramolecular polymers based on cyclodextrins. J Polym Sci A Polym Chem 44(17):5113–5119
Kim HJ, Kim T, Lee M (2011) Responsive nanostructures from aqueous assembly of rigid-flexible block molecules. Acc Chem Res 44(1):72–82
Greef FADT, Smulders MMJ, Wolffs M, Schenning PHJA, Sijbesma PR, Meijer EW (2009) Supramolecular polymerization. Chem Rev 109(11):5687–5754
Takahashi H, Takashima Y, Yamaguchi H, Harada A (2006) Selection between pinching-type and supramolecular polymer-type complexes by α-cyclodextrin−β-cyclodextrin hetero-dimer and hetero-cinnamamide guest dimers. J Org Chem 71(13):4878–4883
Ohga K, Takashima Y, Takahashi H, Kawaguchi Y, Yamaguchi H, Harada A (2005) Preparation of supramolecular polymers from a cyclodextrin dimer and ditopic guest molecules: control of structure by linker flexibility. Macromolecules 38(14):5897–5904
Miyauchi M, Harada A (2004) Construction of supramolecular polymers with alternating a-, b-cyclodextrin units using conformational change induced by competitive guests. J Am Chem Soc 126(37):11418–11419
Miyawaki A, Takashima Y, Yamaguchi H, Harada A (2008) Branched supramolecular polymers formed by bifunctional cyclodextrin derivatives. Tetrahedron 64(36):8355–8361
Jabbari-Farouji S, Schoot PVD (2010) Competing templated and self-assembly in supramolecular polymers. Macromolecules 43(13):5833–5844
Baytekin HT, Baytekin B, Schulz A, Springer A, Gross T, Unger W, Artamonova M, Schlecht S, Lentz D, Schalley AC (2009) Metallo-supramolecular nano-spheres via hierarchical self-assembly. Chem Mater 21(13):2980–2992
Chen JY, Chen CY, Lee HM, Passaglia E, Vizza F, Oberhauser W (2011) Zinc coordination polymers with 2,6-bis(imidazole-1-yl)pyridine and benzene carboxylate: pseudo-supramolecular isomers with and without interpenetration and unprecedented trinodal topology. Cryst Growth Des 11(4):1230–1237
Sessler LJ, Jayawickramarajah J, Sathiosatham M, Sherman LC, Brodbelt S (2003) Novel guanosine-cytidine dinucleotide that self-assembles into a trimeric supramolecule. J Org Lett 5(15):2627–2630
Schmidt R, Stolte M, Grne M, Wrthner F (2011) Hydrogen-bond-directed formation of supramolecular polymers incorporating head-to-tail oriented dipolar merocyanine dyes. Macromolecules 44(10):3766–3776
Jazkewitsch O, Ritter H (2011) Formation and characterization of inclusion complexes of alkyne functionalized poly(epsilon-caprolactone) with beta-cyclodextrin. Pseudo-polyrotaxane-based supramolecular organogels. Macromolecules 44(2):375–382
Xing H, Zhou HT, Yu HQ, Gou ZM, Xiao JX (2011) Participation of the inclusion complexes in the surface adsorbed layer in the mixtures of α-cyclodextrin and cationic-anionic hydrogenated and fluorinated surfactants: a surface tension proof. J Chem Eng Data 56(4):1423–1432
Chen Y, Liu Y (2010) Cyclodextrin-based bioactive supramolecular assemblies. Chem Soc Rev 39(2):495–505
Mura P, Corti G, Maestrelli F, Cirri M (2007) The influence of chitosan on cyclodextrin complexing and solubilizing abilities towards drugs. J Incl Phenom Macrocycl Chem 59(3–4):307–313
Jazkewitsch O, Mondrzyk A, Staffel R, Ritter H (2011) Cyclodextrin‐modified polyesters from lactones and from bacteria: an approach to new drug carrier systems. Macromolecules 44(6):1365–1371
Chan SC, Kuo SW, Chang FC (2005) Synthesis of the organic/inorganic hybrid star polymers and their inclusion complexes with cyclodextrins. Macromolecules 38(8):3099–3107
Zarrabi A, Adeli M, Vossoughi M, Shokrgozar MA (2011) Design and synthesis of novel polyglycerol hybrid nanomaterials for potential applications in drug delivery systems. Macromol Biosci 11(3):383–390
Adeli M, Kalantari M, Zarnegar Z, Kabiri R (2012) Dendritic supramolecules; new multivalent nanocarriers. RSC Adv 2(7):2756–2758
Adeli M, Kalantari M, Sadeghi E, Mahmoudi M (2011) Synthesis of new hybrid nanomaterials: promising systems for cancer therapy. Nanomed: Nanotechnol, BiolMed 7(6):806–817
Tomalia DA, Baker H, Dewald JR, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P (1985) A new class of polymers: starburst-dendritic macromolecules. Polymer 17(1):117–132
Lee ES, Kim D, Youn YS, Oh KT, Bae YH (2008) A novel virusmimetic nanogel vehicle. Angew Chem Int Ed 47(13):2418–2421
Quan CY, Chen JX, Wang HY, Li C, Chang C, Zhang XZ, Zhuo RX (2010) Core-shell nanosized assemblies mediated by the α-β cyclodextrin dimer with a tumor-triggered targeting property. ACSnano 4(7):4211–4219
Xu S, Luo Y, Haag R (2007) Water-soluble pH- responsive dendritic core-shell nanocarriers for polar dyes based on poly(ethylene imine). Macromol Biosci 7:968–974
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Chegeni, B.K., Kakanejadifard, A., Abedi, F. et al. pH-sensitive supramolecular copolydendrimers, new anticancer drug delivery system. Colloid Polym Sci 292, 3337–3346 (2014). https://doi.org/10.1007/s00396-014-3398-2
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DOI: https://doi.org/10.1007/s00396-014-3398-2