A novel lophine-based fluorescence probe and its binding to human serum albumin

Kishikawa, Naoya; Ohyama, Kaname; Saiki, Akane; Matsuo, Aya; Ali, Marwa F.; Wada, Mitsuhiro; Nakashima, Kenichiro; Kuroda, Naotaka

doi:10.1016/j.aca.2013.04.003

Cited by 22 publications

(12 citation statements)

References 36 publications

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“…Perhaps this is another straight testimony for the static fluorescence quenching between globular proteins and imidacloprid. Based on the sight of Kragh-Hansen [49], and also connected several recent reports on the subject of protein-ligand, such as tetracycline, magnetic ferrofluid, retinol and retinoic acid, and lophine-based fluorescence probe [50][51][52][53], it is very clear that the conjugation of imidacloprid with the two globular proteins belongs to moderate binding with respect to the other strong protein-ligand complexes with affinities ranging from 10 6 to 10 8 M À1 .…”

Section: Samplesmentioning

confidence: 99%

Biological assessment of neonicotinoids imidacloprid and its major metabolites for potentially human health using globular proteins as a model

Ding

Peng

2015

Journal of Photochemistry and Photobiology B: Biology

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Section: Samplesmentioning

confidence: 99%

Biological assessment of neonicotinoids imidacloprid and its major metabolites for potentially human health using globular proteins as a model

Ding

Peng

2015

Journal of Photochemistry and Photobiology B: Biology

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“…The triphenylimidazole structural framework has been intensely studied throughout the years, by many different research groups, due to its fluorescence (FL) and chemiluminescence (CL) properties. The typical direct CL of 2,4,5‐triphenylimidazole (also known as lophine) with oxygen in an alkaline media, first described by Radziszewski in 1877, was studied mainly to elucidate its reaction mechanism .…”

Section: Introductionmentioning

confidence: 99%

“…However, lophine and its derivatives were also applied in other CL systems, being used as activators of the peroxyoxalate reaction or enhancers of the luminol transformation . In part, the vast array of application of these molecules, from FL to CL measurements, depends on the high FL quantum yields ( Φ FL > 0.1) presented by them …”

Section: Introductionmentioning

confidence: 99%

The decomposition of triphenylimidazole‐para‐acetate follows specific base catalysis and can be conveniently followed by fluorescence

et al. 2019

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The kinetics of the decomposition reaction of 4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl acetate (1) in basic alcoholic media was investigated, using a simple fluorescence (FL) spectrophotometric procedure. The process was conveniently studied using FL, since the triphenylimidazole-derived ester 1 and its reaction products (the corresponding phenol 2 and phenolate 2 − ) are all highly fluorescent (Φ FL > 37%). By carefully selecting excitation and emission wavelengths, observed rate constants k 1 in the order of 10 −3 to 10 −2 s −1 were obtained from either reactant consumption (λ ex = 300 nm, λ em = 400 nm) or product formation (λ ex = 350 nm, λ em = 475 nm); these were shown to be kinetically equivalent. Intensity-decay time profiles also gave a residual FL intensity parameter, shown to be associated to the distribution of produced species 2 and 2 − , according to the basicity of the medium. Studying the reaction in both methanol (MeOH) and isopropanol (iPrOH), upon addition of HO − , provided evidence that the solvent's conjugate base is the active nucleophilic species.When different bases were used (tBuO − , HO − , DBU and TEA), bimolecular rate constants k bim ranging from 4.5 to 6.5 L mol −1 s −1 were obtained, which proved to be non-dependent on the base pK aH , suggesting specific base catalysis for the decomposition of 1 in alcoholic media. KEYWORDS imidazole, kineticslight emissionlophine, rate constant 1 | INTRODUCTIONThe triphenylimidazole structural framework has been intensely studied throughout the years, by many different research groups, due to its fluorescence (FL) [1][2][3][4][5][6][7][8][9] and chemiluminescence (CL) [10][11][12][13][14][15][16][17][18][19][20][21][22] properties. The typical direct CL of 2,4,5-triphenylimidazole (also known as lophine) with oxygen in an alkaline media, first described by Radziszewski in 1877, [23] was studied mainly to elucidate its reaction mechanism. [11][12][13][18][19][20][21][22]24] However, lophine and its derivatives were also applied in other CL systems, being used as activators of the peroxyoxalate reaction [10] or enhancers of the luminol transformation. [25][26][27] In part, the vast array of application of these molecules, from FL to CL measurements, depends on the high FL quantum yields (Φ FL > 0.1) presented by them. [1][2][3][4][5][6][7][8][9][10]17,[24][25][26][27] In 1993, Kuroda et al. reported that triphenylimidazole-para-acetate (1, IUPAC name 4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl acetate), as well as another three ester analogs based on pertinent fatty acids, could be applied on the evaluation of lipase activity through FL measurements. [8] Although ester 1 itself was not the most suitable for interaction with the lipase, it was primarily used to define the methodology for activity determination. Briefly, the method consisted on hydrolyzing the ester with the enzyme, followed by separation and FL

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“…11,12 Various reagents including dyes, 13 polymers 14 and gold nanoparticles 15 have been used as HSA sensors. Although several fluorescent probes have been reported, it was found that they had low excitation (<500 nm) and emission wavelengths (<600 nm), which may not prevent the interference from the biological autofluorescence.…”

Section: Introductionmentioning

confidence: 99%

A Near Infrared Fluorescent Probe for Sensitive Determination of Human Serum Albumin

Zeng

Zhu

et al. 2016

ANAL. SCI.

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A fluorescent probe 1 has been successfully developed to determine human serum albumin (HSA). Probe 1 expresses a dramatic fluorescence enhancement to HSA without interference from other amino acids. Under the optimal conditions, the calibration graphs are linear over the range of 0 -13.3 μg/mL with the limit of determination of 0.61 μg/mL. Thus, this probe shows high sensitivity and selectivity to HSA.

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A novel lophine-based fluorescence probe and its binding to human serum albumin

Cited by 22 publications

References 36 publications

Biological assessment of neonicotinoids imidacloprid and its major metabolites for potentially human health using globular proteins as a model

Biological assessment of neonicotinoids imidacloprid and its major metabolites for potentially human health using globular proteins as a model

The decomposition of triphenylimidazole‐para‐acetate follows specific base catalysis and can be conveniently followed by fluorescence

A Near Infrared Fluorescent Probe for Sensitive Determination of Human Serum Albumin

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