Photochemically amplified detection of molecular recognition events: an ultra-sensitive fluorescence turn-off binding assay

Gustafson, Tiffany P.; Metzel, Greg A.; Kutateladze, Andrei G.

doi:10.1039/c1ob05289f

Cited by 14 publications

(13 citation statements)

References 16 publications

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“…We used dimethylaminopyridine as catalyst and triethylamine as base, but these conditions turned out to be ineffective . The method involving the formation of an active complex and subsequent coupling with amine also did not give the desired product . We decided to test several other procedures involving coupling reagents (Table ).…”

Section: Resultsmentioning

confidence: 99%

The Coumarin‐Dimer Spring—The Struggle between Charge Transfer and Steric Interactions

Kielesiński

Morawski

Sobolewski

et al. 2017

Chemistry A European J

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The synthesis of a weakly coupled, strongly polarized coumarin dimer has been achieved for the first time. The three-step strategy comprises the Skattebøl formylation followed by the Knoevenagel reaction and the formation of a tertiary amide by using a peptide-type procedure. The molecule consists of two different coumarin moieties: One is a classical donor-acceptor system and the second one possesses a weaker amide donor at the 7-position. The polarized coumarin dimer can form an electronically conjugated structure possessing an electric dipole larger than that of 7-(dimethylamino)coumarin-3-carboxylic acid. The limited flexibility of the inter-coumarin connection results in stable conformers of different electric dipole moments and complex photophysics. In the solid state, this compound has a strongly bent conformation with the two coumarin units forming an angle of around 74°. In solution, two conformers are in equilibrium. The existence of the molecule as two conformers in the ground state has been confirmed by optical studies, and further corroborated by molecular calculations. The fluorescence spectra possess a unique feature: A charge-transfer band (ca. 550 nm) is visible only in nonpolar or weakly polar solvents. Optical spectroscopy studies coupled with molecular calculations allowed us to rationalize this phenomenon: The large amplitude of intramolecular motions is responsible for the conformational isomerization as well as producing a conical intersection between the potential energy surfaces of the excited singlet state and the ground state, which opens an internal conversion channel that effectively competes with the fluorescence of the conformers.

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Section: Resultsmentioning

confidence: 99%

The Coumarin‐Dimer Spring—The Struggle between Charge Transfer and Steric Interactions

Kielesiński

Morawski

Sobolewski

et al. 2017

Chemistry A European J

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“…456 Events, which occur on an attomolar concentration scale, can now be detected via molecular recognition-triggered photoamplified fluorescence quenching. 457 Dithiane-based photolabile tags have also been used for encoding and direct screening of solution-phase combinatorial libraries. 458 …”

Section: Sensitized Releasementioning

confidence: 99%

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

et al. 2012

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“…7-Diethylaminocoumarin-3-carboxylic acid N-hydroxy-succinamide ester (11). 10 (1.0 g, 3.8 mmol) was dissolved in dichloromethane (50 mL), N-hydroxysuccinimide (0.66 g, 5.7 mmol) and EDC (0.87 g, 4.6 mmol) were added.…”

Section: General Procedures For Avidin-xanthone Conjugationmentioning

confidence: 99%

“…and (ii) our implementation of 3D (solution-phase) amplified release of the sensitizer from a pool of masked benzophenones and its application as an ultra-sensitive fluorescence turn-off binding assay. 11…”

Section: Introductionmentioning

confidence: 99%

Externally sensitized deprotection of PPG-masked carbonyls as a spatial proximity probe in photoamplified detection of binding events

Gustafson

Metzel

Kutateladze

2012

Photochem Photobiol Sci

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Externally-sensitized electron-transfer fragmentation in dithiane PPG-protected carbonyls is adopted for detection and amplification of molecular recognition events. The new methodology allows for detection of as low as 50 attomoles of avidin utilizing an imager based on a low sensitivity mass-produced consumer CCD camera. Numeric modelling is carried out to demonstrate the intrinsic limitations of 2D amplification on surfaces and the advantages of unconstrained amplification in a compartmentalized volume of spatially addressable 3D solutions.

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Photochemically amplified detection of molecular recognition events: an ultra-sensitive fluorescence turn-off binding assay

Cited by 14 publications

References 16 publications

The Coumarin‐Dimer Spring—The Struggle between Charge Transfer and Steric Interactions

The Coumarin‐Dimer Spring—The Struggle between Charge Transfer and Steric Interactions

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

Externally sensitized deprotection of PPG-masked carbonyls as a spatial proximity probe in photoamplified detection of binding events

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