Detection and Identification of Designer Drugs by Nanoparticle-based NMR Chemosensing

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2018 Jun 19

PMID 29910928

Citations 7

Authors

Luca Gabrielli

Daniele Rosa-Gastaldo

Marie-Virginie Salvia

Sara Springhetti

Federico Rastrelli

Fabrizio Mancin

Affiliations

Soon will be listed here.

Abstract

Properly designed monolayer-protected nanoparticles (2 nm core diameter) can be used as nanoreceptors for selective detection and identification of phenethylamine derivatives (designer drugs) in water. The molecular recognition mechanism is driven by the combination of electrostatic and hydrophobic interactions within the coating monolayer. Each nanoparticle can bind up to 30-40 analyte molecules. The affinity constants range from 10 to 10 M and are modulated by the hydrophobicity of the aromatic moiety in the substrate. Detection of drug candidates (such as amphetamines and methamphetamines) is performed by using magnetization (NOE) or saturation (STD) transfer NMR experiments. In this way, the NMR spectrum of the drug is isolated from that of the mixture, allowing broad-class multianalyte detection and even identification of unknowns. The introduction of a dimethylsilane moiety in the coating monolayer allows performing STD experiments in complex mixtures. In this way, a detection limit of 30 μM is reached with standard instruments.

Citing Articles

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References

Pieters G, Cazzolaro A, Bonomi R, Prins L . Self-assembly and selective exchange of oligoanions on the surface of monolayer protected Au nanoparticles in water. Chem Commun (Camb). 2012; 48(13):1916-8. DOI: 10.1039/c2cc16926f. View

Porchetta A, Vallee-Belisle A, Plaxco K, Ricci F . Using distal-site mutations and allosteric inhibition to tune, extend, and narrow the useful dynamic range of aptamer-based sensors. J Am Chem Soc. 2012; 134(51):20601-4. PMC: 3866043. DOI: 10.1021/ja310585e. View

Shcherbakova E, Zhang B, Gozem S, Minami T, Zavalij P, Pushina M . Supramolecular Sensors for Opiates and Their Metabolites. J Am Chem Soc. 2017; 139(42):14954-14960. PMC: 5682928. DOI: 10.1021/jacs.7b06371. View

Zhao Y, Swager T . Detection and differentiation of neutral organic compounds by 19F NMR with a tungsten calix[4]arene imido complex. J Am Chem Soc. 2013; 135(50):18770-3. PMC: 4019753. DOI: 10.1021/ja4106804. View

Pieters G, Pezzato C, Prins L . Controlling supramolecular complex formation on the surface of a monolayer-protected gold nanoparticle in water. Langmuir. 2012; 29(24):7180-5. DOI: 10.1021/la304316z. View

Diez-Castellnou M, Salvia M, Springhetti S, Rastrelli F, Mancin F . Nanoparticle-Assisted Affinity NMR Spectroscopy: High Sensitivity Detection and Identification of Organic Molecules. Chemistry. 2016; 22(47):16957-16963. DOI: 10.1002/chem.201603578. View

Rastrelli F, Jha S, Mancin F . Seeing through macromolecules: T2-filtered NMR for the purity assay of functionalized nanosystems and the screening of biofluids. J Am Chem Soc. 2009; 131(40):14222-4. DOI: 10.1021/ja904737r. View

Biavardi E, Federici S, Tudisco C, Menozzi D, Massera C, Sottini A . Cavitand-grafted silicon microcantilevers as a universal probe for illicit and designer drugs in water. Angew Chem Int Ed Engl. 2014; 53(35):9183-8. DOI: 10.1002/anie.201404774. View

Riccardi L, Gabrielli L, Sun X, De Biasi F, Rastrelli F, Mancin F . Nanoparticle-Based Receptors Mimic Protein-Ligand Recognition. Chem. 2017; 3(1):92-109. PMC: 5521955. DOI: 10.1016/j.chempr.2017.05.016. View

10.

Axthelm J, Gorls H, Schubert U, Schiller A . Fluorinated Boronic Acid-Appended Bipyridinium Salts for Diol Recognition and Discrimination via (19)F NMR Barcodes. J Am Chem Soc. 2015; 137(49):15402-5. DOI: 10.1021/jacs.5b10934. View

11.

Lobo Vicente J, Chassaigne H, Holland M, Reniero F, Kolar K, Tirendi S . Systematic analytical characterization of new psychoactive substances: A case study. Forensic Sci Int. 2016; 265:107-15. DOI: 10.1016/j.forsciint.2016.01.024. View

12.

Moreno D, Diaz de Grenu B, Garcia B, Ibeas S, Torroba T . A turn-on fluorogenic probe for detection of MDMA from ecstasy tablets. Chem Commun (Camb). 2012; 48(24):2994-6. DOI: 10.1039/c2cc17823k. View

13.

Minami T, Esipenko N, Akdeniz A, Zhang B, Isaacs L, Anzenbacher Jr P . Multianalyte sensing of addictive over-the-counter (OTC) drugs. J Am Chem Soc. 2013; 135(40):15238-43. DOI: 10.1021/ja407722a. View

14.

Salvia M, Ramadori F, Springhetti S, Diez-Castellnou M, Perrone B, Rastrelli F . Nanoparticle-assisted NMR detection of organic anions: from chemosensing to chromatography. J Am Chem Soc. 2014; 137(2):886-92. DOI: 10.1021/ja511205e. View

15.

Bonomi R, Selvestrel F, Lombardo V, Sissi C, Polizzi S, Mancin F . Phosphate diester and DNA hydrolysis by a multivalent, nanoparticle-based catalyst. J Am Chem Soc. 2008; 130(47):15744-5. DOI: 10.1021/ja801794t. View

16.

Lucarini M, Franchi P, Pedulli G, Pengo P, Scrimin P, Pasquato L . EPR study of dialkyl nitroxides as probes to investigate the exchange of solutes between the ligand shell of monolayers of protected gold nanoparticles and aqueous solutions. J Am Chem Soc. 2004; 126(30):9326-9. DOI: 10.1021/ja048554f. View

17.

Axthelm J, Askes S, Elstner M, Reddy G U, Gorls H, Bellstedt P . Fluorinated Boronic Acid-Appended Pyridinium Salts and F NMR Spectroscopy for Diol Sensing. J Am Chem Soc. 2017; 139(33):11413-11420. DOI: 10.1021/jacs.7b01167. View

18.

Boccalon M, Bidoggia S, Romano F, Gualandi L, Franchi P, Lucarini M . Gold nanoparticles as drug carriers: a contribution to the quest for basic principles for monolayer design. J Mater Chem B. 2020; 3(3):432-439. DOI: 10.1039/c4tb01536c. View

19.

Daly B, Ling J, de Silva A . Current developments in fluorescent PET (photoinduced electron transfer) sensors and switches. Chem Soc Rev. 2015; 44(13):4203-11. DOI: 10.1039/c4cs00334a. View

20.

Znaleziona J, Ginterova P, Petr J, Ondra P, Valka I, Sevcik J . Determination and identification of synthetic cannabinoids and their metabolites in different matrices by modern analytical techniques - a review. Anal Chim Acta. 2015; 874:11-25. DOI: 10.1016/j.aca.2014.12.055. View