Pseudorotaxane capped mesoporous silica nanoparticles for 3,4-methylenedioxymethamphetamine (MDMA) detection in water

Abstract

Mesoporous silica nanoparticles loaded with fluorescein and capped by a pseudorotaxane, formed between a naphthalene derivative and cyclobis(paraquat-p-phenylene) (CBPQT), were used for the selective and sensitive fluorogenic detection of 3,4-methylenedioxymethamphetamine (MDMA).

Mesoporous Silica‐Based Materials with Bactericidal Properties

“…Moreover, the pore‐blockers should respond to appropriate external or internal triggers to close or open the well‐defined pores, causing on‐demand intelligent cargo delivery . Various porekeepers including polymers (e.g., polymer poly(2‐vinylpyridine) (PVP), poly(N‐succinimidyl acrylate), poly(2‐dimethylaminoethyl methacrylate), poly(acrylic acid) brush), host–guest assemblies (e.g., Cyclodextrins, cucurbit,uril, pillararenes), inorganic nanomaterials (e.g., Au NPs, quantum dots, Ag NPs, cerium oxide NPs, manganese oxide NPs, and reduced graphene), and biomacromolecules (e.g., peptides, nucleic acids, saccharides, and proteins) have been employed under certain internal or external stimuli, such as pH, temperature, light, redox potential, ultrasound, small molecules, biomolecules, and or a combination of these stimuli, to achieve controllable DDSs based on mesoporous silica nanoparticles (MSNs) …”

Overview of the Evolution of Silica-Based Chromo-Fluorogenic Nanosensors

“…MSNs capped with pseudo-rotaxanes have been designed for the selective and sensitive detection of 3,4-methylenedioxymethamphetamine (MDMA, also known as ecstasy) in water [56]. For this purpose, MSNs were loaded with fluorescein, externally functionalized with a naphthalene derivative, and finally, capped via the formation of inclusion complexes between the anchored 1-naphtol subunits from the scaffold and the cyclobis(paraquat- p -phenylene)hexafluorophosphate macrocycle ([CBPQT][PF 6 ] 4 ).…”

Chromogenic and Fluorogenic Probes for the Detection of Illicit Drugs

“…Lozano‐Torres and co‐workers recount the preparation of mesoporous silica nanoparticles (MSNs) capped with pseudorotaxanes for the selective and sensitive fluorogenic detection of MDMA in water (Scheme ) . In a first step, the external surface of the MSNs is functionalized with a naphthalene derivative, and this is followed by the encapsulation of fluorescein inside the porous network of the inorganic scaffold.…”

“…- [33] MA molecular recognition (perylene bisimidefluorophore, and two cholesterol subunits) vapor5.5 10 À6 amines, organic solvents, water,a pple pomace [34] MDMA NPs water0.95 cocaine, heroin, methadone, and morphine [ 35] MA molecular recognition (aminefunctionalized polyfluorene) THF 2.5 10 À5 pethidine and EPH [36] MDMA NPs water-AMP,g lucose, glycine, and sarcosine [37] AMPH,M ETH, MDMA; and DA molecular recognition (macrocyclic) H 2 O/MeOH (7:3, v/v, pH 7.4) 7.4 10 À6 , 1.3 10 À6 , 8.0 10 À6 ,and 6.7 10 À5 - [38] MDMA and MDA colorimetric reaction sulfuric acid aqueous (75 %, w/v) 0.19 - [39,40] MA NPs toluene and vapor -o-toluidine, hexylamine, diethylamine,dibutylamine, allylamine, trimethylamine, and aniline [41] catecholaminemolecularr ecognition water-biogenica mines, sugars, neurotransmitters, and aminoa cids [42] phenothiazinedrugs spectrophotometric methodsulfuric acid -- [43] ChemistryOpen 2018, 7,401 -428 www.chemistryopen.org 2018 The Authors. Publishedb yWiley-VCH Verlag GmbH &Co. KGaA, Weinheim STIMULANT DRUGS PEA UV n-hexane1 0 À4 phenylethanolamine [44] d-a nd l-a-phenylethylamines fluorescencechiral sensors MeCN -- [45] PEPH hydrochloride spectrofluorometricmethodPBS(pH 7.8) 0.5 additiveore xcipients present in the pharmaceuticalsf ormulations [46] cocaine, MDMA/MDA, and heroine/morphine spectralfluorescence signature (SFS) measurements water -- [47] MA aptasensor combined with AuNPs (colorimetric assay) human urine 1.2 10 À4 pethidine, triazolam, barbital, morphine, ketamine, and diazepam [49] MA aptasensorand oxidationr eaction of afluorophore water 7.4 10 À9 ketamine,norketamine, morphine, methadone, cocaine, mephedrone, cathinone, methcathinone, 3-trifluromethylphenyl piperazine,1 -3-trifluromethylphenyl piperazine, 3,4-methylenedioxy pyrovalerona, MDA, MDMA, EDDP,and mCPP [50] cocaineaptamern anomachine (FRET processa llowed or not depending on the analyte) water 1.5 10 À4 - [51] cocaineaptamern anomachine and amplified aptamer nanomachine (quenching off/on process) water 3.0 10 À5 for normal and 3.5 10 À17 for amplified process - [52] cocaineaptamern anomachine (quenching off/on process)…”

“…Lozano-Torres and co-workers recountt he preparation of mesoporoussilica nanoparticles (MSNs)capped with pseudorotaxanesf or the selectivea nd sensitive fluorogenic detection of MDMAi nw ater (Scheme 4). [35] In af irst step, the external surface of the MSNs is functionalized with an aphthalene derivative, and this is followed by the encapsulationo ff luorescein inside the porousn etwork of the inorganic scaffold. In a second step, the loaded MSNs are capped upon the addition of the cyclobis(paraquat-p-phenylene) hexafluorophosphate ([CBPQT][PF 6 ] 4 )m acrocycle, which forms inclusion complexes with 1-naphtol subunitsa ttached onto the externals urface of the nanoparticles.…”