Limits...
Evaluation of poly(amidoamine) dendrimers as potential carriers of iminodiacetic derivatives using solubility studies and 2D-NOESY NMR spectroscopy.

Markowicz M, Szymański P, Ciszewski M, Kłys A, Mikiciuk-Olasik E - J Biol Phys (2012)

Bottom Line: We reported that PAMAM dendrimers contribute to significant solubility enhancement of iminodiacetic acid analogues.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 (1)H 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmaceutical Chemistry and Drug Analysis, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, Poland.

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 (1)H NMR and 2D-NOESY spectroscopy. The (1)H 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 (1)H 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.

No MeSH data available.


Synthesis of derivatives of N-(2-phenylamine- 2-oxoethyl)iminodiacetic acid
© Copyright Policy
Related In: Results  -  Collection


getmorefigures.php?uid=PMC3473130&req=5

Sch1: Synthesis of derivatives of N-(2-phenylamine- 2-oxoethyl)iminodiacetic acid

Mentions: For synthesis of iminodiacetic acid derivatives, we applied method described by A. Nunn [27]. This method was previously used to synthesize N-(3-bromo-2,4,6-trimethylacetanilide)iminodiacetic acid (mebrofenin), but we also prepared other compounds by means of this method (Scheme 1).Scheme 1


Evaluation of poly(amidoamine) dendrimers as potential carriers of iminodiacetic derivatives using solubility studies and 2D-NOESY NMR spectroscopy.

Markowicz M, Szymański P, Ciszewski M, Kłys A, Mikiciuk-Olasik E - J Biol Phys (2012)

Synthesis of derivatives of N-(2-phenylamine- 2-oxoethyl)iminodiacetic acid
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3473130&req=5

Sch1: Synthesis of derivatives of N-(2-phenylamine- 2-oxoethyl)iminodiacetic acid
Mentions: For synthesis of iminodiacetic acid derivatives, we applied method described by A. Nunn [27]. This method was previously used to synthesize N-(3-bromo-2,4,6-trimethylacetanilide)iminodiacetic acid (mebrofenin), but we also prepared other compounds by means of this method (Scheme 1).Scheme 1

Bottom Line: We reported that PAMAM dendrimers contribute to significant solubility enhancement of iminodiacetic acid analogues.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 (1)H 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmaceutical Chemistry and Drug Analysis, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, Poland.

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 (1)H NMR and 2D-NOESY spectroscopy. The (1)H 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 (1)H 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.

No MeSH data available.