Abstract
Solubility is a key property influencing behavior of compounds in nature, science, biomedical applications, etc. Hydrophobicity and poor solubility of drugs and other bioactive compounds limit their possible applications in drug delivery and formulation development. Therefore approximately 40 % of newly developed drugs are rejected by the pharmaceutical industry and will never benefit a patient owing to poor bioavailability due to low water solubility and/or cell membrane permeability. In most cases, this problem can be solved by dendrimers. Many examples of dendrimers with different cores, branches, structures, hydrophilic surface groups, and hydrophobic pockets are described, including PEGylated dendrimers. The application of dendrimers as solubility enhancers for many drugs, such as anticancer drugs, antidepressants, antifungal drugs, antihemorrhagic drugs, antihistaminics, anti-inflammatory drugs, and antimicrobial drugs, is discussed. Solubility is in close relation with delivery, bioavailability, and/or cell membrane permeability; therefore see also these chapters.
Keywords
- Atom Transfer Radical Polymerization
- Lower Critical Solution Temperature
- Mefenamic Acid
- Hyperbranched Polymer
- PAMAM Dendrimers
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Astruc, D., Boisselier, E., Ornelas, C.: Dendrimers designed for functions: from physical, photophysical, and supramolecular properties to applications in sensing, catalysis, molecular electronics, photonics, and nanomedicine. Chem. Rev. 110(4), 1857–1959 (2010)
Bai, S., Thomas, C., Rawat, A., Ahsan, F.: Recent progress in dendrimer-based nanocarriers. Crit. Rev. Ther. Drug Carrier Syst. 23(6), 437–495 (2006)
Balogh, L.: Dendrimer 101. Adv. Exp. Med. Biol. 620, 136–155 (2007)
Bencini, M., Ranucci, E., Ferruti, P., Trotta, F., Donalisio, M., Cornaglia, M., Lembo, D., Cavalli, R.: Preparation and in vitro evaluation of the antiviral activity of the acyclovir complex of a β-cyclodextrin/poly(amidoamine) copolymer. J. Control Rel. 126(1), 17–25 (2008)
Benito, J., Gomez-Garcia, M., Ortiz Mellet, C., Baussanne, I., Defaye, J., Garcia Fernandez, J.: Optimizing saccharide-directed molecular delivery to biological receptors: design, synthesis, and biological evaluation of glycodendrimer-cyclodextrin conjugates. J. Am. Chem. Soc. 126(33), 10355–10363 (2004)
Chabre, Y.M., Brisebois, P.P., Abbassi, L., Kerr, S.C., Fahy, J.V., Marcotte, I., Roy, R.: Hexaphenylbenzene as a rigid template for the straightforward syntheses of “star-shaped” glycodendrimers. J. Org. Chem. 76(2), 724–727 (2011)
Chen, Q., Cui, Y., Cao, J., Han, B.H.: Water-soluble conjugated polyelectrolyte with pendant glycocluster: synthesis and its interaction with heparin. Polymer 52(2), 383–390 (2011)
Cheng, Y., Gao, Y., Rao, T., Li, Y., Xu, T.: Dendrimer-based prodrugs: design, synthesis, screening and biological evaluation. Comb. Chem. High Through Screen. 10(5), 336–349 (2007)
Cheng, Y., Xu, Z., Ma, M., Xu, T.: Dendrimers as drug carriers: applications in different routes of drug administration. J. Pharm. Sci. 97(1), 123–143 (2008)
Fahmi, A., Pietsch, T., Appelhans, D., Gindy, N., Voit, B.: Water-soluble CdSe nanoparticles stabilised by dense-shell glycodendrimers. New J. Chem. 33(4), 703–706 (2009)
Gillies, E., Frechet, J.: Dendrimers and dendritic polymers in drug delivery. Drug Discov. Today 10(1), 35–43 (2005)
Gu, L., Luo, P.G., Wang, H., Meziani, M.J., Lin, Y., Veca, L.M., Cao, L., Lu, F., Wang, X., Quinn, R.A., Wang, W., Zhang, P., Lacher, S., Sun, Y.P.: Single-walled carbon nanotube as a unique scaffold for the multivalent display of sugars. Biomacromol. 9(9), 2408–2418 (2008)
Guo, B., Sun, X., Zhou, Y., Yan, D.: Supramolecular self-assembly and controllable drug release of thermosensitive hyperbranched multiarm copolymers. Sci. China. Chem. 53, 487–494 (2010)
Gupta, U., Agashe, H., Asthana, A., Jain, N.: Dendrimers: novel polymeric nanoarchitectures for solubility enhancement. Biomacromol. 7(3), 649–658 (2006)
Jacobson, K.A.: GPCR ligand–dendrimer (GLiDe) conjugates: future smart drugs? Trends Pharmacol. Sci. 31(12), 575–579 (2010)
Kim, H.Y., Sohn, J., Wijewickrama, G.T., Edirisinghe, P., Gherezghiher, T., Hemachandra, M., Lu, P.Y., Chandrasena, R.E., Molloy, M.E., Tonetti, D.A., Thatcher, G.R.: Click synthesis of estradiol–cyclodextrin conjugates as cell compartment selective estrogens. Bioorg. Med. Chem. 18(2), 809–821 (2010)
Kojima, C., Toi, Y., Harada, A., Kono, K.: Aqueous solubilization of fullerenes using poly(amidoamine) dendrimers bearing cyclodextrin and poly(ethylene glycol). Bioconjug. Chem. 19(11), 2280–2284 (2008)
Paleos, C., Tsiourvas, D., Sideratou, Z.: Molecular engineering of dendritic polymers and their application as drug and gene delivery systems. Mol. Pharmaceut. 4(2), 169–188 (2007)
Prajapati, R., Tekade, R., Gupta, U., Gajbhiye, V., Jain, N.: Dendimer-mediated solubilization, formulation development and in vitro-in vivo assessment of piroxicam. Mol. Pharmaceut. 6(3), 940–950 (2009)
Qiu, S., Huang, H., Dong, C.M.: Synthesis and pH-sensitive self-assembly of dendritic poly(amidoamine)-b- poly(l-glutamate) biohybrids. Chinese J. Polym. Sci. 27(6), 797–805 (2009)
Sebestik, J., Niederhafner, P., Jezek, J.: Peptide and glycopeptide dendrimers and analogous dendrimeric structures and their biomedical applications. Amino Acids 40(2), 301–370 (2011)
Shi, Y., Porter, W., Merdan, T., Li, L.: Recent advances in intravenous delivery of poorly water-soluble compounds. Expert Opin. Drug Deliv. 6(12), 1261–1282 (2009)
Svenson, S.: Dendrimers as versatile platform in drug delivery applications. Eur. J. Pharm. Biopharm. 71(3), 445–462 (2009)
Svenson, S., Chauhan, A.: Dendrimers for enhanced drug solubilization. Nanomedicine 3(5), 679–702 (2008)
Svenson, S., Tomalia, D.A.: Nanoparticulates as Drug Carriers. Dendrimers as Nanoparticular Drug Carriers, pp. 277–306. Imperial College Press, London (2006)
Tekade, R., Kumar, P., Jain, N.: Dendrimers in oncology: an expanding horizon. Chem. Rev. 109(1), 49–87 (2009)
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 2012 Springer-Verlag Wien
About this chapter
Cite this chapter
Šebestík, J., Reiniš, M., Ježek, J. (2012). Dendrimers and Solubility. In: Biomedical Applications of Peptide-, Glyco- and Glycopeptide Dendrimers, and Analogous Dendrimeric Structures. Springer, Vienna. https://doi.org/10.1007/978-3-7091-1206-9_10
Download citation
DOI: https://doi.org/10.1007/978-3-7091-1206-9_10
Published:
Publisher Name: Springer, Vienna
Print ISBN: 978-3-7091-1205-2
Online ISBN: 978-3-7091-1206-9
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)