Selective fluorescence sensing and quantification of uric acid by naphthyridine-based receptor in biological sample

Sahoo, Prithidipa; Das, Sujoy; Sarkar, Himadri Sekhar; Maiti, Kalipada; Uddin, Md. Raihan; Mandal, Sukhendu

doi:10.1016/j.bioorg.2017.03.002

Cited by 18 publications

(14 citation statements)

References 54 publications

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“…For example, Sahoo et al synthesized a naphthyridine-based fluorescent probe that demonstrated 1:1 binding stoichiometry with urate. 33 Rather than using indicator displacement, the probe functioned as both the indicator and the urate ligand, exhibiting quenching upon binding. Both aromatic stacking and hydrogen bonding were shown to contribute to the interaction with urate.…”

Section: Resultsmentioning

confidence: 99%

A Copper(II) Macrocycle Complex for Sensing Biologically Relevant Organic Anions in a Competitive Fluorescence Assay: Oxalate Sensor or Urate Sensor?

et al. 2020

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Fluorescence sensing of oxalate has garnered some attention in the past two decades as a result of this anion’s prominence and impact on society. Previous work on oxalate sensors and other divalent anion sensors has led to the conclusion that the sensors are selective for the anion under investigation. However, sensor selectivity is often determined by testing against a relatively small array of “guest” molecules or analytes and studies often exclude potentially interfering compounds. For example, studies on oxalate sensors have excluded compounds such as citrate and urate, which are anions in the biological matrices where oxalate is measured ( e.g ., urine, blood, and bacterial lysate). In the present study, we reassessed the selectivity of a dinuclear copper(II) macrocycle (Cu 2 L) in an eosin Y displacement assay using biologically relevant anions. Although previously reported as selective for oxalate, we found greater indicator displacement (fluorescence response) for urate and oxaloacetate and a significant response to citrate. These anions are larger than oxalate and do not appear to fit into the putative binding pocket of Cu 2 L. Consistent with previous reports, Cu 2 L did not release eosin Y in the presence of several other dicarboxylates, including adipate, glutarate, malate (except at 10 mM), fumarate, succinate, or malonate (except at 10 mM), and the monocarboxylate acetate. This was demonstrated by the failure of the anions to reverse eosin Y quenching by Cu 2 L. We also assessed, for the first time, other monocarboxylates, including butyrate, pyruvate, lactate, propionate, and formate. None of these anions were able to displace eosin Y, indicating no interaction with Cu 2 L that interfered with the eosin Y binding site. Single-crystal X-ray crystallography revealed that nonselective binding of the anions is likely partly caused by readily accessible copper(II) ions on the external surface of Cu 2 L. In addition, π–π stacking of urate with the aromatic groups of Cu 2 L cannot be ruled out as a contributor to binding. We conclude that Cu 2 L is not suitable for oxalate sensing in a biological matrix unless interfering compounds are selectively removed or masked.

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Section: Resultsmentioning

confidence: 99%

A Copper(II) Macrocycle Complex for Sensing Biologically Relevant Organic Anions in a Competitive Fluorescence Assay: Oxalate Sensor or Urate Sensor?

et al. 2020

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“…On the other hand, the excited‐state information can be speculated upon based on the ground‐state results. For instance, Sahoo et al reported a PET fluorescent probe for uric acid . The mechanism was assessed by considering the distinct distributions of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of both the probe and its hydrogen‐bonded uric acid complex based on their ground‐state geometries.…”

Section: Methodsmentioning

confidence: 99%

“…Ground‐state calculations, such as Hartree–Fock (HF), DFT, and more accurate second‐order Møller–Plesset (MP2) calculations, may be considered as the first step to the electronically excited states of fluorescent probes. In other words, all excited‐state calculations start with the results of ground‐state calculations.…”

Section: Methodsmentioning

confidence: 99%

“…Ground-state calculations, such as Hartree-Fock (HF), 63 DFT, 29,64-66 and more accurate second-order Møller-Plesset (MP2) calculations, 67,68 65 The mechanism was assessed by considering the distinct distributions of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of both the probe and its hydrogen-bonded uric acid complex based on their ground-state geometries. Another example of ground-state calculation concerns molecular electrostatic potentials for the fluorescent probe, such as the work of So et al 69 In their probe, the oxygen atoms of the four-membered ring and the amide ring are very negative.…”

Section: Ground-state Calculationsmentioning

confidence: 99%

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The sensing mechanism studies of the fluorescent probes with electronically excited state calculations

Han

2017

WIREs Comput Mol Sci

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Recent research has indicated that fluorescent probes have tremendous potential for the selective detection of chemical and biological species. Over the past decade, researchers have proposed a series of fluorescence‐based sensing mechanisms of such probes by the calculation of their electronic excited states. Investigations of sensing mechanisms have been based on deep insights into the interactions between probe molecules and their target species, as well as their fluorescence properties. Advances in calculation methods, modeling software, and computational power have enabled researchers to use excited‐state theoretical calculations to reproduce experimental fluorescence phenomena and then provide molecular‐level explanations thereof. In this advanced review, we describe the evolution of theoretical studies on excited‐state sensing mechanisms for fluorescent probes that respond to target species. Focusing on calculation methods that facilitate investigation of the photophysical properties and excited‐state dynamics of probes, we emphasize sensing mechanisms mainly reported by our group. Most of these studies have been supported by theoretical predictions based on time‐dependent density functional theory. For this most popular excited‐state calculation method, vertical excitation energy, excited‐state geometrical optimization and a scan of the excited‐state potential energy surface should be noted in the calculation of electronic and molecular differences between the excited‐state probe and its reaction product with the target analyte. These state‐of‐the‐art calculations are of great importance for unraveling details of fluorescence‐based sensing mechanisms, including photochemical reactions (such as twist intramolecular charge transfer and excited‐state proton transfer) and excited‐state electronic processes (such as intramolecular charge transfer and photoinduced electron transfer). These studies have generated new and inspirational mechanistic proposals and have provided a systematic approach for the development of efficient fluorescent sensors. WIREs Comput Mol Sci 2018, 8:e1351. doi: 10.1002/wcms.1351 This article is categorized under: Structure and Mechanism > Computational Biochemistry and Biophysics Theoretical and Physical Chemistry > Spectroscopy

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“…As part of our ongoing research towards developing uorophores for purine and pyrimidine derivatives, 26,27 here, we prepared a new and simple chemosensor, a pyrene-appended 5hydroxyisophthalic acid derivative (PIA), which showed efficient uorescence signal upon selective binding with cytosine in Scheme 1 "Turn-on" fluorescence changing mechanism of PIA upon addition of cytosine.…”

Section: Introductionmentioning

confidence: 99%

“Turn-on” fluorescence sensing of cytosine: development of a chemosensor for quantification of cytosine in human cancer cells

Sarkar¹,

Sahoo²,

Mandal

et al. 2017

RSC Adv.

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Selective fluorescence sensing and quantification of uric acid by naphthyridine-based receptor in biological sample

Cited by 18 publications

References 54 publications

A Copper(II) Macrocycle Complex for Sensing Biologically Relevant Organic Anions in a Competitive Fluorescence Assay: Oxalate Sensor or Urate Sensor?

A Copper(II) Macrocycle Complex for Sensing Biologically Relevant Organic Anions in a Competitive Fluorescence Assay: Oxalate Sensor or Urate Sensor?

The sensing mechanism studies of the fluorescent probes with electronically excited state calculations

“Turn-on” fluorescence sensing of cytosine: development of a chemosensor for quantification of cytosine in human cancer cells

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