title: Bio-inspired solid phase extraction sorbent material for cocaine: a cross reactivity study.
abstract: The binding specificity of a bio-inspired hexapeptide (QHWWDW) versus cocaine and four other drugs such as 3,4-methylenedioxy-N-methylamphetamine (MDMA), 3,4-methylenedioxy-N-ethylamphetamine (MDEA), phencyclidine and morphine was computationally studied and then experimentally confirmed in solid phase extraction (SPE) followed by liquid chromatography-mass spectrometry (LC/MS) detection. In simulation, the hexapeptide-drug complexes were docked with different scoring functions and considering pH chemical environment. In experimental, the cross reactivity of the selected hexapeptide was tested as SPE sorbent versus cocaine and other four drugs using buffer solutions at pH 4 and 7. Significant differences in specific retention were found between cocaine (97% of recovery) and both morphine (45% of recovery) and phencyclidine (60% of recovery), but less for ecstasies (average recovery 69%). In agreement with docking simulation, the hexapeptide showed the highest recovery with best specificity versus cocaine at pH 7 with an experimentally binding constant of 2.9 × 10(6)M(-1). The bio-inspired sorbent material analytical performances were compared with a commercial reversed phase cartridge confirming the hexapeptide specificity to cocaine and validating simulated data.
authors.affiliation: Department of Chemistry, Sapienza University of Rome, 00185 Rome, Italy.
authors.forename: Camilla
authors.initials: C
authors.lastname: Montesano
authors.affiliation: Faculty of Bioscience and Technology for Food, Agriculture and Environment, University of Teramo, 64023 Teramo, Italy. Electronic address: msergi@unite.it.
authors.forename: Manuel
authors.initials: M
authors.lastname: Sergi
authors.affiliation: Laboratory of Computational and Theoretical Chemistry, Faculty of Chemistry, University of Havana, 10400 Havana, Cuba.
authors.forename: German
authors.initials: G
authors.lastname: Perez
authors.affiliation: Department of Chemistry, Sapienza University of Rome, 00185 Rome, Italy.
authors.forename: Roberta
authors.initials: R
authors.lastname: Curini
authors.affiliation: Faculty of Bioscience and Technology for Food, Agriculture and Environment, University of Teramo, 64023 Teramo, Italy.
authors.forename: Dario
authors.initials: D
authors.lastname: Compagnone
authors.affiliation: Faculty of Bioscience and Technology for Food, Agriculture and Environment, University of Teramo, 64023 Teramo, Italy. Electronic address: mmascini@unite.it.
authors.forename: Marcello
authors.initials: M
authors.lastname: Mascini
mesh_terms: D002853:Chromatography, Liquid / Q000379:methods*; D003042:Cocaine / Q000737:chemistry / Q000302:isolation & purification*; D003429:Cross Reactions; D006863:Hydrogen-Ion Concentration; D018817:N-Methyl-3,4-methylenedioxyamphetamine / Q000737:chemistry; D009842:Oligopeptides / Q000737:chemistry*; D052616:Solid Phase Extraction / Q000379:methods*; D053719:Tandem Mass Spectrometry / Q000379:methods*
chemical_list: D009842:Oligopeptides; C055137:phenylalanyl-glycyl-histidyl-statyl-alanyl-phenylalanine methyl ester; D003042:Cocaine; D018817:N-Methyl-3,4-methylenedioxyamphetamine
keywords: Cocaine; Cross reactivity; Liquid chromatography–mass spectrometry; Molecular modeling; Peptides; Solid phase extraction