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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.


a The 1H-1H NOESY spectrum of compound 2. b The 1H-1H NOESY spectrum of complex between compound 2 and G2 PAMAM dendrimer
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Fig7: a The 1H-1H NOESY spectrum of compound 2. b The 1H-1H NOESY spectrum of complex between compound 2 and G2 PAMAM dendrimer

Mentions: The NOESY spectrum of compound 2 in DMSO solution at a standard mixing time of 300 ms is shown in Fig. 7a. Strong NOE cross-peaks are observed between the carboxyl protons and methylene groups. Weaker interactions are also observed, such as those between the amide group and methylene group, the methyl in the aromatic ring, protons of the aromatic ring, protons of aromatic ring, and carboxyl groups. NOESY spectra of free compounds were prepared in order to properly assign NOE cross-peaks between the drug and dendrimer.Fig. 7


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)

a The 1H-1H NOESY spectrum of compound 2. b The 1H-1H NOESY spectrum of complex between compound 2 and G2 PAMAM dendrimer
© Copyright Policy
Related In: Results  -  Collection

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

Fig7: a The 1H-1H NOESY spectrum of compound 2. b The 1H-1H NOESY spectrum of complex between compound 2 and G2 PAMAM dendrimer
Mentions: The NOESY spectrum of compound 2 in DMSO solution at a standard mixing time of 300 ms is shown in Fig. 7a. Strong NOE cross-peaks are observed between the carboxyl protons and methylene groups. Weaker interactions are also observed, such as those between the amide group and methylene group, the methyl in the aromatic ring, protons of the aromatic ring, protons of aromatic ring, and carboxyl groups. NOESY spectra of free compounds were prepared in order to properly assign NOE cross-peaks between the drug and dendrimer.Fig. 7

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.