Improved method for the preparation of poly[N5-(2-hydroxyethyl)-l-glutamine] by aminolysis of poly(γ-benzyl-l-glutamate)

Marre, Anne De; Soyez, Heidi; Schacht, Etienne; Pytela, Jindřich

doi:10.1016/0032-3861(94)90786-2

Cited by 24 publications

(13 citation statements)

References 13 publications

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“…The degree of P(BLG) aminolysis was controlled by changing the mole ratio of octylamine to benzyl glutamate repeat units. The polypeptide degradation during aminolysis was to a large extent prevented by the addition of 2‐HP as a bifunctional catalyst …”

Section: Resultsmentioning

confidence: 99%

“…The polypeptide degradation during aminolysis was to a large extent prevented by the addition of 2-HP as a bifunctional catalyst. 47 MALDI-TOF mass spectra of P(BLG-oa) samples reveal that all macromolecules contain the hexyl group at one chain end that originates from the initiator, whereas the amino end group presented in original P(BLG) samples transformed during aminolysis into a pyroglutamic group via intramolecular cyclization reaction with the adjacent benzyl ester group (Fig. 2).…”

Section: Synthesis Of Water-soluble Alkyl-modified Sodium Poly(glutammentioning

confidence: 99%

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Synthesis of alkyl-modified poly(sodium glutamate)s for preparation of polymer-protein nanoparticles in combination withN,N,N-trimethyl chitosan

Pahovnik

Grujić

Cegnar³

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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The negatively charged, water‐soluble, hydrophobically modified poly(sodium glutamate)s containing different amounts of alkyl grafts were synthesized. First, poly(γ‐benzyl‐L‐glutamate) was prepared by ring‐opening polymerization of the corresponding N‐carboxyanhydride, which was in the next step aminolysed with octylamine. After removal of the remaining benzyl protective groups, the alkyl‐modified poly(sodium glutamate)s [P(Glu‐oa)] were obtained and, together with the oppositely charged N,N,N‐trimethyl chitosan (TMC), used for the preparation of nanoparticles (NPs) of a recombinant granulocyte colony‐stimulating factor (GCSF) protein by polyelectrolyte complexation method. It is observed that, beside electrostatic interaction, the hydrophobic grafts on poly(sodium glutamate)s significantly contribute to association efficiency (AE) with GCSF protein. The addition of TMC solution to the dispersion of GCSF/P(Glu‐oa) complexes results in formation of much more defined NPs with high AE and final protein loading. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 2976–2985

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Water-soluble Alkyl-modified Sodium Poly(glutammentioning

confidence: 99%

Synthesis of alkyl-modified poly(sodium glutamate)s for preparation of polymer-protein nanoparticles in combination withN,N,N-trimethyl chitosan

Pahovnik

Grujić

Cegnar³

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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“…This block copolymer was synthesized by the method previously described. [12] The aminolysis of PBLG with n-aminoalkanols was carried out according to the method reported by Marre et al [15] who tried to optimize the reaction conditions for aminolysis by minimizing the main-chain cleavage. In their study, it was found that aminolysis of the side-chain ester of PBLG with a 2-aminoalkanol occurred effectively at 40 8C at a reaction time of 24 h using five equivalents of 2-HP with respect to the ester group.…”

Section: Resultsmentioning

confidence: 99%

Effects of Poly(N-isopropylacrylamide) (PNIPAAm) on the Conformational Change of Poly(N 5-hydroxyalkyl glutamine) (PHAG) in PHAG-PNIPAAm Block Copolymer with Temperature

Cheon

Kim

Park

et al. 2001

Macromol. Chem. Phys.

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Diblock copolymers consisting of poly(N 5‐hydroxyalkylglutamine) (PHAG) and poly(N‐isopropylacrylamide) (PNIPAAm) were prepared by aminolysis with aminoalkanols of the side‐chain ester of poly(γ‐benzyl L‐glutamate) (PBLG) as a part of PBLG‐PNIPAAm block copolymers. The molecular weight ratio of the initial PBLG to the resulting PHAG was nearly 0.35. The effect of PNIPAAm on the conformational change of PHAG in PHAG‐PNIPAAm block copolymers with temperature was investigated by circular dichroism. Poly[N 5‐(2‐hydroxyethyl)‐L‐glutamine] (PHEG) and the PHEG‐PNIPAAm copolymer (GNE) stayed in a randomly coiled conformation whereas poly[N 5‐(3‐hydroxypropyl)‐L‐glutamine] (PHPG), poly(N 5‐(4‐hydroxybutyl)‐L‐glutamine) (PHBG), PHPG‐PNIPAAm copolymer (GNP), and PHBG‐PNIPAAm copolymer (GNB) underwent conformational transitions with temperature. The conformational change of the PHPG block in GNP copolymer occurred from an α‐helix to a random coil after the incorporation of PNIPAAm into the copolymer. The thermodynamic parameters of the thermally induced helix‐coil transition for PHBG and PHBG‐PNIPAAm in aqueous solution were calculated.

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“…This polymer was converted into the water-soluble PHEG by aminolysis with twenty equivalents of 2-aminoethanol in the presence of five equivalents of 2-hydroxypyridine as a bifunctional catalyst [48]. The synthesis of dendritic-PHEG polymers was similar to that of the linear PHEG, but instead of using tri-n-butylamine as the initiator, a fourthgeneration poly(amido amine) (PAMAM, Starburst ® ) dendrimer with ethylene diamine core was used as the macro-initiator.…”

Section: Preparation and Characterization Of Linear And Dendritic Polmentioning

confidence: 99%

“…The synthesis of linear and dendritic-PHEG was described earlier [48,49]. Briefly, the γ-benzyl-L-glutamate was prepared by selective esterification of L-glutamic acid, according to the method of Gutmann and Boissonas [47].…”

Section: Preparation and Characterization Of Linear And Dendritic Polmentioning

confidence: 99%

Dendritic Poly-[N-(2-Hydroxyethyl)-L-Glutamine] as Potential Drug Carrier

Winne¹,

Vanderkerken²,

Hoste³

et al. 2004

Journal of Bioactive and Compatible Polymers

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Dendritic poly-[N-(2-hydroxyethyl)-L-glutamine] (PHEG) with different molecular weights were synthesized by aminolysis of dendritic poly-(γ-benzyl-L-glutamate) (PBG), which was obtained by polymerization of the corresponding N-carboxyanhydride (NCA) with poly(amido amine) (PAMAM, starburst ® ) of the fourth generation as initiator. Dynamic light scattering (DLS) was used to determine the size of the polymeric carriers and to compare the dendritic polymer to the linear analogue. The body distribution and blood clearance of 125 I-radiolabelled linear and dendritic PHEG with similar molecular weight were investigated in female BALB/c mice.

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Improved method for the preparation of poly[N5-(2-hydroxyethyl)-l-glutamine] by aminolysis of poly(γ-benzyl-l-glutamate)

Cited by 24 publications

References 13 publications

Synthesis of alkyl-modified poly(sodium glutamate)s for preparation of polymer-protein nanoparticles in combination withN,N,N-trimethyl chitosan

Synthesis of alkyl-modified poly(sodium glutamate)s for preparation of polymer-protein nanoparticles in combination withN,N,N-trimethyl chitosan

Effects of Poly(N-isopropylacrylamide) (PNIPAAm) on the Conformational Change of Poly(N 5-hydroxyalkyl glutamine) (PHAG) in PHAG-PNIPAAm Block Copolymer with Temperature

Dendritic Poly-[N-(2-Hydroxyethyl)-L-Glutamine] as Potential Drug Carrier

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