Site-Selective Hydrogen-Bonding-Induced Fluorescence Quenching of Highly Solvatofluorochromic GFP-like Chromophores

Huang, Guan-Jhih; Ho, Jau Der; Chetti, Prabhakar; Liu, Yi-Hung; Peng, Shie‐Ming; Yang, Jye‐Shane

doi:10.1021/ol302237k

Cited by 78 publications

(141 citation statements)

References 31 publications

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“…37 Thus, it is likely that ATMND binds either C21 or T20 within the three-way junction of the aptamer through a three-point hydrogen bond. 38,39 Additionally, we observed a large negative enthalpy change in ITC experiments, which also indicates the formation of hydrogen bonds between ATMND and the aptamer. We believe that ATMND forms these hydrogen bonds and possibly cooperates with adjacent nucleotides via π-stacking interaction to significantly quench its fluorescence.…”

Section: ■ Results and Discussionmentioning

confidence: 61%

A Label-Free Aptamer-Fluorophore Assembly for Rapid and Specific Detection of Cocaine in Biofluids

et al. 2014

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We report a rapid and specific aptamer-based method for one-step cocaine detection with minimal reagent requirements. The feasibility of aptamer-based detection has been demonstrated with sensors that operate via target-induced conformational change mechanisms, but these have generally exhibited limited target sensitivity. We have discovered that the cocaine-binding aptamer MNS-4.1 can also bind the fluorescent molecule 2-amino-5,6,7-trimethyl-1,8-naphthyridine (ATMND) and thereby quench its fluorescence. We subsequently introduced sequence changes into MNS-4.1 to engineer a new cocaine-binding aptamer (38-GC) that exhibits higher affinity to both ligands, with reduced background signal and increased signal gain. Using this aptamer, we have developed a new sensor platform that relies on the cocaine-mediated displacement of ATMND from 38-GC as a result of competitive binding. We demonstrate that our sensor can detect cocaine within seconds at concentrations as low as 200 nM, which is 50-fold lower than existing assays based on target-induced conformational change. More importantly, our assay achieves successful cocaine detection in body fluids, with a limit of detection of 10.4, 18.4, and 36 μM in undiluted saliva, urine, and serum samples, respectively.

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Section: ■ Results and Discussionmentioning

confidence: 61%

A Label-Free Aptamer-Fluorophore Assembly for Rapid and Specific Detection of Cocaine in Biofluids

et al. 2014

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“…[1][2][3][4][5][6][7][8] This proposition has been extended to other unconstrained GFP chromophore analogues. [9][10][11][12] For example both p-HBDI and p-ABDI (Chart 1) have a Z-E isomerisation quantum yield (F ZE ) B 0.5 and F f B 0.0001. 9 However, meta analogues of these two molecules i.e.…”

Section: Introductionmentioning

confidence: 99%

“…[9][10][11][12] It has been reported that no other internal conversion plays any important role towards the non-radiative excited state decay channel. 9,11,12 It has also been shown for constrained GFP chromophore analogues where Z-E isomerisation is reduced that F f is enhanced.…”

Section: Introductionmentioning

confidence: 99%

Strong electron donation induced differential nonradiative decay pathways for para and meta GFP chromophore analogues

Chatterjee

Mandal

Gude

et al. 2015

Phys. Chem. Chem. Phys.

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Z-E Isomerisation because of rotation around the exocyclic double bond (known as the τ-twist) and not any other internal conversion has been reported to be the major nonradiative decay channel for non-hydroxylic unconstrained para and meta GFP chromophore analogues. The equation Φf + 2ΦZE = 1 has been shown to hold well for both para and meta GFP chromophore analogues. If the above equation holds true, then upon reducing the extent of Z-E isomerisation (ΦZE), the fluorescence quantum yield (Φf) should increase. To probe the above proposition two sets of non-hydroxylic unconstrained para and meta GFP chromophore analogues were synthesized. Quite interestingly by introducing the strongly electron donating -NEt2 group to the benzenic moiety these para and meta GFP chromophore analogues were shown to exhibit differential optical behaviour w.r.t. the extent of the solvatochromic shift, Φf, ΦZE, and τf. For the first time it has been shown that the well accepted equation Φf + 2ΦZE = 1 does not hold at all for these non-hydroxylic unconstrained meta analogues. Although ΦZE has been shown to be <10%, Φf is much lower than the expected near unity value for these meta analogues. After detailed investigation into the nonradiative excited state decay channel, contrary to literature reports, energy gap law governed internal conversion and not Z-E isomerisation was shown to be the major nonradiative decay channel for these meta analogues. Two models are put forward to understand the differential optical behaviour of these para and meta GFP chromophore analogues. Support from X-ray crystal structures, NMR experiments, and computational calculations has also been provided.

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“…The abandon of this alternative conformation indicates that the benzylidenedimethylimidazolinone (BDI) π system has a high tendency to be coplanar. This is indeed supported by the case of M1 , in which the N,N ‐dimethylamino group encounters no steric hindrance and is coplanar with the BDI π system.…”

Section: Resultsmentioning

confidence: 62%

o‐Amino Analogs of Green Fluorescence Protein Chromophore: Photoisomerization, Photodimerization and Aggregation‐induced Emission

Huang

Lin

Liu

et al. 2014

Photochem & Photobiology

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The photochemical properties of three o-amino analogs of the green fluorescence protein chromophore O0, O1 and O8 (o-ABDIs) have been investigated and compared with those of the m- and p-amino isomers (m-ABDIs and p-ABDIs) in solutions, aggregates, and the solid state. In aprotic solvents, the fluorescence competes with the Z → E photoisomerization for all cases, and the o-ABDIs display a fluorescence quantum efficiency of 1-6%, lying between the m-ABDIs of 5-48% and the p-ABDIs of < 0.1%. The fluorescence of both the o- and m-ABDIs is nearly quenched in protic solvents, attributable to the solvent-solute hydrogen bonding (SSHB) interactions. The phenomenon of aggregation-induced emission observed for O8 in poor solvents resembles the behavior of M8 as a consequence of exclusion of the SSHB interactions and restriction of internal rotation for molecules located inside the aggregates. The occurrence of [2 + 2] photodimerization for O0 in the solid state is unique among the ABDIs, and the X-ray crystal structures of O0 and the photodimer OD reveal the head-to-tail syn-oriented stereochemistry. Analysis on the X-ray crystal structures of O0, O1, M0, M1 and P0 shows that not only the pairwise topochemical geometry but also the columnar packing mode is important in determining the photodimerization reactivity.

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Site-Selective Hydrogen-Bonding-Induced Fluorescence Quenching of Highly Solvatofluorochromic GFP-like Chromophores

Cited by 78 publications

References 31 publications

A Label-Free Aptamer-Fluorophore Assembly for Rapid and Specific Detection of Cocaine in Biofluids

A Label-Free Aptamer-Fluorophore Assembly for Rapid and Specific Detection of Cocaine in Biofluids

Strong electron donation induced differential nonradiative decay pathways for para and meta GFP chromophore analogues

o‐Amino Analogs of Green Fluorescence Protein Chromophore: Photoisomerization, Photodimerization and Aggregation‐induced Emission

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