title: Synthesis of new series of α-cyclodextrin esters as dopamine carrier molecule.
abstract: A new series of amphiphilic α-cyclodextrins were synthesized by grafting N-acylated amino acids [valine, leucine, phenylalanine, methionine, and tryptophan (3a-e)] to the primary hydroxyl groups via ester bond formation. The synthetic pathway involves selective hexa-bromination of the primary hydroxyls followed by per-substitution with the carboxylate moiety of the N-acetyl residues in the presence of DBU (1,8-diazabicyclo[5,4,0]undec-7-ene). The ability of the synthetic compounds for the extraction of dopamine was studied. The results showed a considerable ability of some of the amphiphilic compounds for the extraction of dopamine into octanol phase from water. To complete the study, the binding affinity of dopamine toward the synthetic host molecules was calculated by using of the molecular docking technique.
authors.affiliation: Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad 917751436, Iran.
authors.forename: Seyed Mohammad
authors.initials: SM
authors.lastname: Seyedi
authors.forename: Hamid
authors.initials: H
authors.lastname: Sadeghian
authors.forename: Atena
authors.initials: A
authors.lastname: Jabbari
authors.forename: Amir
authors.initials: A
authors.lastname: Assadieskandar
authors.forename: Hamideh
authors.initials: H
authors.lastname: Momeni
mesh_terms: D004298:Dopamine / Q000737:chemistry / Q000302:isolation & purification*; D050483:Dopamine Plasma Membrane Transport Proteins / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D047391:alpha-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D050483:Dopamine Plasma Membrane Transport Proteins; D004952:Esters; D047391:alpha-Cyclodextrins; D004298:Dopamine