A smart supramolecular device for the detection of t,t-muconic acid in urine

Abstract

An indicator displacement assay is applied in the fluorescence detection of urinary t,t-muconic acid at the occupational level.

A Nanoprobe Based on Gated Mesoporous Silica Nanoparticles for The Selective and Sensitive Detection of Benzene Metabolite t,t‐Muconic Acid in Urine

“…Within these metal complexes, those formed by bistren cryptands (obtained by the reaction of two tris(2‐aminoethyl)amine and three dialdehyde linkers) and Cu II have been extensively used for the selective coordination of several dicarboxylates [30–32] . In particular, very recently, Amendola and co‐workers have demonstrated that t,t‐MA can coordinate effectively to a dicopper(II) bistren azacryptand and developed an indicator displacement assay for the fluorescence sensing of this benzene metabolite [33] …”

“…The bistren cryptand was prepared by reaction of 4,4’‐biphenyldicarboxaldehyde with tris(2‐aminoethyl)amine and further reduction of the imine bonds with sodium borohydride. The final dicopper(II) complex 2 was obtained by refluxing the azacryptand with copper(II) nitrate [33] …”

“…[30][31][32] In particular,v ery recently,A mendola and co-workers have demonstrated that t,t-MA can coordinate effectively to ad icopper(II) bistren azacryptanda nd developeda ni ndicator displacement assay for the fluorescences ensing of this benzene metabolite. [33] Based on the above, and following our interest in the development of hybrido rganic-inorganicm aterials for the design of chromo-fluorogenics ensing protocols as an alternative to molecular based probes, [34][35][36][37][38][39][40][41] we report herein the synthesis and characterization of ag ated nanodevice for the selectivea nd sensitiveq uantification of t,t-MA in urine. The nanodevice used mesoporouss ilica nanoparticles (MSNs) [42,43] as inorganic scaffold with the pores loaded with sulforhodamine B( SRh B) and capped with an inclusion complex formed between at erephthalic acid derivative (grafted onto the external surface of the solid) and ad icopper(II) bistren azacryptand (Scheme 1).…”

“…The bistren cryptand was prepared by reaction of 4,4'-biphenyldicarboxaldehyde with tris(2-aminoethyl)amine and further reduction of the imine bonds with sodium borohydride.T he final dicopper(II) complex 2 was obtainedb yr efluxing the azacryptand with copper(II) nitrate. [33] All prepared solids were characterized using standard techniques( Supporting Information). Figure 1a shows the PXRD patterns of the as made, S0 and S4 nanoparticles.…”

Towards Building Blocks for Supramolecular Architectures Based on Azacryptates

“…Even if the 1,4-phenyldicarboxylate's bite is not optimal for our receptor, the interaction of 6-TAMRA with the cage in aqueous solution is expected to be favored by hydrophobic effects and by π-π* interactions between the rhodamine core and the triphenyl spacers [32,33]. Moreover, 6-TAMRA is commercially available and it has been successfully employed for the fluorescent detection of dicarboxylates in water, e.g., using the dicopper azacryptate with diphenyl spacers as the receptor [16,34].…”