Preparation of liposomes with glucose binding sites: liposomes containing di-branched amino acid derivatives.
Di-branched amino acid derivatives, such as dihexadecyl-glutamate-glutamine (DHD-glu-gln), dihexadecyl-glutamate-asparagine (DHD-glu-asn) and dihexadecyl-glutamate-glutamic acid (DHD-glu-glu), were synthesized, and then incorporated into lipid vesicles (liposomes) using dipalmitoylphosphatidylcholine (DPPC). To form binding sites toward glucose, the liposomes containing amino acid derivatives were mixed with glucose above the phase transition temperature (PTT) of DPPC and subsequently the temperature was lowered below the PTT. The glucose-binding affinity of liposomes containing amino acid derivative with or without glucose imprinting was evaluated by surface plasmon resonance (SPR) and equilibrium dialysis technique. SPR of liposomes containing each amino acid derivative or three amino acid derivatives revealed that only the liposomes containing all three amino acid derivatives had glucose-binding affinity and that the glucose-imprinting process was essential to fix the amino acid derivatives into a glucose binding site on the liposomes. Equilibrium dialysis studies of glucose-imprinted liposomes produced curvilinear Scatchard plots, indicating that the amino acid derivatives play a role in glucose binding. Di-branched amino acid derivatives synthesized in this study are promising agent for the development of biocompatible synthetic glucose binding materials.
Seong
Hasoo
H
Department of Pharmaceutics, School of Pharmacy, Purdue University, West Lafayette, IN 47907, USA.
Choi
Won-Moon
WM
Kim
Jin-Chul
JC
Thompson
David H
DH
Park
Kinam
K
D015060:1,2-Dipalmitoylphosphatidylcholine / Q000737:chemistry; D000597:Amino Acids, Branched-Chain / Q000138:chemical synthesis / Q000737:chemistry*; D001665:Binding Sites; D004151:Dipeptides / Q000737:chemistry; D004187:Disaccharides / Q000737:chemistry; D005947:Glucose; D008081:Liposomes / Q000138:chemical synthesis* / Q000737:chemistry*; D013816:Thermodynamics
D000597:Amino Acids, Branched-Chain; D004151:Dipeptides; D004187:Disaccharides; D008081:Liposomes; D015060:1,2-Dipalmitoylphosphatidylcholine; D005947:Glucose