2012
DOI: 10.1073/pnas.1112264109
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Exclusive recognition of sarcosine in water and urine by a cavitand-functionalized silicon surface

Abstract: A supramolecular approach for the specific detection of sarcosine, recently linked to the occurrence of aggressive prostate cancer forms, has been developed. A hybrid active surface was prepared by the covalent anchoring on Si substrates of a tetraphosphonate cavitand as supramolecular receptor and it was proven able to recognize sarcosine from its nonmethylated precursor, glycine, in water and urine. The entire complexation process has been investigated in the solid state, in solution, and at the solid-liquid… Show more

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Cited by 63 publications
(86 citation statements)
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References 30 publications
(25 reference statements)
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“…[72][73][74][75][76][77][78] Hundreds of synthetic derivatives are known, including dimeric caged forms known as (hemi)carcerands. 79-81 These molecules have been developed, primarily, for exploitation of the rich molecular recognition chemistry exhibited by their shape-persistent concave cavities.…”
Section: Hypothesesmentioning
confidence: 99%
“…[72][73][74][75][76][77][78] Hundreds of synthetic derivatives are known, including dimeric caged forms known as (hemi)carcerands. 79-81 These molecules have been developed, primarily, for exploitation of the rich molecular recognition chemistry exhibited by their shape-persistent concave cavities.…”
Section: Hypothesesmentioning
confidence: 99%
“…Diagnostic upfield shifts of the guest signals were observed, as expected for hosted species that experience the shielding effect of the cavity. [17] In particular, the signals of the N-CH 3 moiety moved over 3 ppm upfield to δ = -0.53 ppm; other resonances attributed to the sarcosine moiety as well as to the phenanthroline unit were also shifted. The 31 P resonance of the four P=O groups moved downfield by almost 5 ppm (from δ = 5.9 to 10.8 ppm; Figure S2 in the Supporting Information).…”
Section: Self-assembly In Solutionmentioning
confidence: 97%
“…towards a sarcosine unit [17] connected to a phenanthroline ligand (1), followed by the coordination of 1 with the europium β-diketonate complex 2 used as the luminescent probe. The related nonluminescent and diamagnetic yttrium β-diketonate 3 was chosen as the reference compound for the NMR spectroscopic characterization in solution and for photophysical control experiments on the surface.…”
Section: Design and Strategymentioning
confidence: 99%
See 1 more Smart Citation
“…Phosphonate cavitands are well-known for their ability to complex positively charged species and neutral molecules by a synergistic combination of weak interactions. [2] We have recently demonstrated [3] that a silicon surface decorated with phosphonate cavitands can selectively recognize sarcosine (whose presence in urine is linked with an aggressive form of prostate cancer) from other non-methylated amino acids in biological fluids. The same ability is currently being exploited for the molecular recognition of carboxylic acids of social interest (see Fig.…”
mentioning
confidence: 99%