Supramolecular Sensors for Opiates and Their Metabolites

Abstract

The present study highlights a sensing approach for opiates using acyclic cucurbituril (aCBs) sensors comprising four glycouril units terminated on both ends with naphthalene fluorophore walls. The connectivity between the glycourils and naphthalene rings largely defines the opening size of the cucurbituril cavity and its diameter. The large hydrophobic binding cavity is flexible and is able to adapt to guests of various size and topology. The recognition event between the aCBs and guests results in modification of the fluorescence of the terminal walls, a fluorescence response that can be used to sense the drugs of abuse morphine, heroin, and oxycodone as well as their metabolites. Molecular dynamics is employed to understand the nature of the binding interactions. A simple three sensor cross-reactive array enables the determination of drugs and their metabolites in water with high fidelity and low error. Quantitative experiments performed in urine using a new three-way calibration model allows for determination of drugs and their metabolites using one sensor from a single fluorescence reading.

Non-contact identification and differentiation of illicit drugs using fluorescent films

“…Cheng and co-workers 10 , 26 – 28 reported several fluorescence methods for the detection of methamphetamine (MAPA) and ketamine, and the lowest detection limit (DL) in vapor phase of MAPA is ~180 ppb, and 50 pg cm −2 for ketamine in aqueous phase. Recently, Pavel and co-workers 29 , 30 reported a supramolecular sensor array composed of fluorescent cucurbit[n]uril-type receptors, which enables the detection of pseudo-ephedrine and opiates as well as their metabolites in human urine. The DLs of the detections are lower than those reported for solid phase extraction-high-performance liquid chromatography.…”

Acyclic Cucurbit[n]uril‐Type Receptors: Aromatic Wall Extension Enhances Binding Affinity, Delivers Helical Chirality, and Enables Fluorescence Sensing

“…Given the potential to use anthracene walled M3 as a component of sensing arrays, we measured its UV/Vis spectrum (Figure S7) in water and determined its molar extinction coefficient ( ϵ =1.28×10 5 m −1 cm −1 ) at λ max =370 nm. Both the ϵ and λ max values of M3 are larger than for M2 ( ϵ =1.66×10 4 m −1 cm −1 ; λ max =282), the 1,8‐substituted isomer of M2 ( ϵ =1.58×10 4 m −1 cm −1 ; λ max =301 nm), and triptycene walled glycoluril tetramer ( ϵ =6.6×10 4 m −1 cm −1 ; λ max =214 nm) which enhances the potential of M3 in sensing applications [27c, 32] . The inherent solubility of M3 in water (=30 m m ) was sufficient to enable studies of its molecular recognition properties and tease out the impact of the anthracene walls using M2 as comparator.…”

Supramolecular Polymerization with Dynamic Self-Sorting Sequence Control

“…Conventional chromatographic techniques, mass spectrometry, Raman and FTIR spectrometry are very time-consuming, expensive and not applicable to on-site monitoring, as well as require many cleanup steps and trained personnel. 60,61 However, fluorescence method is simple, rapid, sensitive, convenient to carry and suitable for on-site detection. Heroin and morphine are well-known narcotic drugs that belong to a class of drugs known as opioids.…”