Abstract
The interactions between dendrimers and different types of drugs are nowadays one of the most actively investigated areas of the pharmaceutical sciences. The interactions between dendrimers and drugs can be divided into: internal encapsulation, external electrostatic interaction, and covalent conjugation. In the present study, we investigated the potential of poly(amidoamine) (PAMAM) dendrimers for solubility of four iminodiacetic acid derivatives. We reported that PAMAM dendrimers contribute to significant solubility enhancement of iminodiacetic acid analogues. The nature of the dendrimer–drug complexes was investigated by 1H NMR and 2D-NOESY spectroscopy. The 1H NMR analysis proved that the water-soluble supramolecular structure of the complex was formed on the basis of ionic interactions between terminal amine groups of dendrimers and carboxyl groups of drug molecules, as well as internal encapsulation. The 2D-NOESY analysis revealed interactions between the primary amine groups of PAMAM dendrimers and the analogues of iminodiacetic acid. The results of solubility studies together with 1H NMR and 2D-NOESY experiments suggest that the interactions between PAMAM dendrimers of generation 1–4 and derivatives of iminodiacetic acid are based on electrostatic interactions and internal encapsulation. Electronic supplementary material The online version of this article (doi:10.1007/s10867-012-9277-5) contains supplementary material, which is available to authorized users.
Highlights
Dendrimers, a relatively new class of chemical compounds, are large, complex molecules, which possess, in comparison to traditional linear polymers, well-defined chemical structure
It has been proven that various types of dendrimers in both original and modified forms contribute to the enhancement of solubility of hydrophobes and that generation number, pH of the solvent, temperature, and dendritic architecture are the factors that influence the efficiency of dendrimers as solubilizing agents
We described the interaction between PAMAM dendrimers of generation 1–4 and four analogues of iminodiacetic acid
Summary
Dendrimers, a relatively new class of chemical compounds, are large, complex molecules, which possess, in comparison to traditional linear polymers, well-defined chemical structure. Polyamidoamine (PAMAM) dendrimers were the first dendrimers that were synthesized [6, 7]. These molecules and their modifications have received widespread attention throughout the world and are under the most active investigation. Nowadays host-guest properties of dendritic polymers are under scientific investigation and have gained a crucial position in the field of supramolecular chemistry. Interaction between biologically active compounds and dendrimers may be a consequence of electrostatic interactions which may occur between PAMAM dendrimers and acidic, water insoluble molecules such as benzoic acid and salicylic acid. Non-polar groups at the ends of dendrimer branches enable dendrimers to act as micelles which may be utilized as molecular vehicles to transport guest molecules between organic and inorganic phases [3, 11]
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
