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Synthesis and characterization of Fatty acid/amino Acid self-assemblies.

Gajowy J, Bolikal D, Kohn J, Fray ME - J Funct Biomater (2014)

Bottom Line: These poly(aliphatic/aromatic-ester-amide)s were further reacted with poly(ethylene glycol) (PEG) and poly(ethylene glycol methyl ether) of different molecular masses, thus resulting in ABA type (hydrophilic-hydrophobic-hydrophilic) triblock copolymers.The polymers were found to spontaneously self-assemble into nanoparticles with sizes in the range 196-239 nm and critical micelle concentration (CMC) of 0.125-0.250 mg/mL.The results are quite promising and these materials are capable of self-organizing into well-defined micelles/nanospheres encapsulating bioactive molecules, e.g., vitamins or antibacterial peptides for antibacterial coatings on medical devices.

View Article: PubMed Central - PubMed

Affiliation: Department of Biomaterials and Microbiological Technologies, The West Pomeranian University of Technology, Szczecin, Al. Piastow 45, 70-311 Szczecin, Poland. jgajowy@zut.edu.pl.

ABSTRACT
In this paper, we discuss the synthesis and self-assembling behavior of new copolymers derived from fatty acid/amino acid components, namely dimers of linoleic acid (DLA) and tyrosine derived diphenols containing alkyl ester pendent chains, designated as "R" (DTR). Specific pendent chains were ethyl (E) and hexyl (H). These poly(aliphatic/aromatic-ester-amide)s were further reacted with poly(ethylene glycol) (PEG) and poly(ethylene glycol methyl ether) of different molecular masses, thus resulting in ABA type (hydrophilic-hydrophobic-hydrophilic) triblock copolymers. We used Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopies to evaluate the chemical structure of the final materials. The molecular masses were estimated by gel permeation chromatography (GPC) measurements. The self-organization of these new polymeric systems into micellar/nanospheric structures in aqueous environment was evaluated using ultraviolet/visible (UV-VIS) spectroscopy, dynamic light scattering (DLS) and transmission electron microscopy (TEM). The polymers were found to spontaneously self-assemble into nanoparticles with sizes in the range 196-239 nm and critical micelle concentration (CMC) of 0.125-0.250 mg/mL. The results are quite promising and these materials are capable of self-organizing into well-defined micelles/nanospheres encapsulating bioactive molecules, e.g., vitamins or antibacterial peptides for antibacterial coatings on medical devices.

No MeSH data available.


Spectra of initial reactants (a) DTE, (b) DLA and esterification product (c) DTE-DLA.
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jfb-05-00211-f006: Spectra of initial reactants (a) DTE, (b) DLA and esterification product (c) DTE-DLA.

Mentions: The chemical structure of new copolymers was also characterized with 1H NMR. The detailed analysis of 1H NMR spectra for initial materials and esterification product is shown in Figure 6. The following shifts were found for DTE derivative: 9.23, 9.14 ppm (s, Ar-OH), 8.24–8.23 (d, –NH–). 6.97–6.63 ppm (Ar-H), 4.35 (dd, CH of tyrosine), 3.98 (t, –OCH2– of the pendent ester group), 2.81 ppm (ddd, –CH2–), 2.62 ppm (t, –CH2–), 2.51 (DMSO-d), 2.31 (t, –CH2–), 1.47, (m, –CH2–), 1.27 (m, –CH2–), 0.86 (t, –CH3). The detailed analysis of 1H NMR spectrum for DLA revealed the following shifts: 7.26 ppm (s, chloroform–d), 2.35 (t, –CH2–), 1.64 (t, –CH2–), 1.26 (m, –CH2–), 0.86 (m, –CH3). Finally, the DTE-DLA spectrum indicates the presence of a peak at 2.82 ppm characteristic for carbodiimide activation of carboxylic group in fatty acid. This peak disappears after reaction with PEG (Figure 7) along with simultaneous appearance of a characteristic signal at 3.65 ppm.


Synthesis and characterization of Fatty acid/amino Acid self-assemblies.

Gajowy J, Bolikal D, Kohn J, Fray ME - J Funct Biomater (2014)

Spectra of initial reactants (a) DTE, (b) DLA and esterification product (c) DTE-DLA.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4285403&req=5

jfb-05-00211-f006: Spectra of initial reactants (a) DTE, (b) DLA and esterification product (c) DTE-DLA.
Mentions: The chemical structure of new copolymers was also characterized with 1H NMR. The detailed analysis of 1H NMR spectra for initial materials and esterification product is shown in Figure 6. The following shifts were found for DTE derivative: 9.23, 9.14 ppm (s, Ar-OH), 8.24–8.23 (d, –NH–). 6.97–6.63 ppm (Ar-H), 4.35 (dd, CH of tyrosine), 3.98 (t, –OCH2– of the pendent ester group), 2.81 ppm (ddd, –CH2–), 2.62 ppm (t, –CH2–), 2.51 (DMSO-d), 2.31 (t, –CH2–), 1.47, (m, –CH2–), 1.27 (m, –CH2–), 0.86 (t, –CH3). The detailed analysis of 1H NMR spectrum for DLA revealed the following shifts: 7.26 ppm (s, chloroform–d), 2.35 (t, –CH2–), 1.64 (t, –CH2–), 1.26 (m, –CH2–), 0.86 (m, –CH3). Finally, the DTE-DLA spectrum indicates the presence of a peak at 2.82 ppm characteristic for carbodiimide activation of carboxylic group in fatty acid. This peak disappears after reaction with PEG (Figure 7) along with simultaneous appearance of a characteristic signal at 3.65 ppm.

Bottom Line: These poly(aliphatic/aromatic-ester-amide)s were further reacted with poly(ethylene glycol) (PEG) and poly(ethylene glycol methyl ether) of different molecular masses, thus resulting in ABA type (hydrophilic-hydrophobic-hydrophilic) triblock copolymers.The polymers were found to spontaneously self-assemble into nanoparticles with sizes in the range 196-239 nm and critical micelle concentration (CMC) of 0.125-0.250 mg/mL.The results are quite promising and these materials are capable of self-organizing into well-defined micelles/nanospheres encapsulating bioactive molecules, e.g., vitamins or antibacterial peptides for antibacterial coatings on medical devices.

View Article: PubMed Central - PubMed

Affiliation: Department of Biomaterials and Microbiological Technologies, The West Pomeranian University of Technology, Szczecin, Al. Piastow 45, 70-311 Szczecin, Poland. jgajowy@zut.edu.pl.

ABSTRACT
In this paper, we discuss the synthesis and self-assembling behavior of new copolymers derived from fatty acid/amino acid components, namely dimers of linoleic acid (DLA) and tyrosine derived diphenols containing alkyl ester pendent chains, designated as "R" (DTR). Specific pendent chains were ethyl (E) and hexyl (H). These poly(aliphatic/aromatic-ester-amide)s were further reacted with poly(ethylene glycol) (PEG) and poly(ethylene glycol methyl ether) of different molecular masses, thus resulting in ABA type (hydrophilic-hydrophobic-hydrophilic) triblock copolymers. We used Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopies to evaluate the chemical structure of the final materials. The molecular masses were estimated by gel permeation chromatography (GPC) measurements. The self-organization of these new polymeric systems into micellar/nanospheric structures in aqueous environment was evaluated using ultraviolet/visible (UV-VIS) spectroscopy, dynamic light scattering (DLS) and transmission electron microscopy (TEM). The polymers were found to spontaneously self-assemble into nanoparticles with sizes in the range 196-239 nm and critical micelle concentration (CMC) of 0.125-0.250 mg/mL. The results are quite promising and these materials are capable of self-organizing into well-defined micelles/nanospheres encapsulating bioactive molecules, e.g., vitamins or antibacterial peptides for antibacterial coatings on medical devices.

No MeSH data available.