Exclusive formation of imino[4 + 4]cycloaddition products with biologically relevant amines: plausible candidates for acrolein biomarkers and biofunctional modulators

Tsutsui, Atsuko; Pradipta, Ambara R.; Saigitbatalova, Elena; Kurbangalieva, Almira; Tanaka, Katsunori

doi:10.1039/c4md00383g

Cited by 21 publications

(14 citation statements)

References 48 publications

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“…Acrolein substantially has a longer half-life and more toxic to cells than ROS [5], the major oxidative stress factors that lead to a variety of disorders [6]. Notably, the strong association between acrolein with various diseases has made the acrolein become of great interest as a potential biomarker for improving current diagnosis and therapeutic targets [7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Methods for Acrolein Detection: Recent Advances and Applications

Pradipta

Tanaka

2020

J. Idn. Chem. Soc.

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Acrolein holds excellent potential as a critical biomarker in various oxidative stress-related diseases, and direct measurement of acrolein in biological systems is becoming essential to provide information for diagnosis and therapeutic purposes. In this review, we will discuss some available techniques for the detection of acrolein from biological samples. A conventional analytical method for the detection of acrolein by using high-performance liquid chromatography analysis after derivatization with 3-aminophenol is available. However, it is not suitable for high-throughput assay and inconvenient for measurement in clinical practice. On the other hand, we have recently discovered that phenyl azide can rapidly and selectively react with acrolein in a click manner to provide 4-formyl-1,2,3-triazoline through 1,3-dipolar cycloaddition. Moreover, we have successfully utilized this acrolein-azide click reaction as a simple and robust method for detecting and visualizing acrolein generated by live cells. Herein, we will describe our reaction-based acrolein sensor and its application to detect and visualize breast cancer tissues. We utilized the azide-acrolein click reaction-based method to discriminate breast cancer lesion from the normal breast gland, which resected from breast cancer patients. This method is the first example of an organic synthetic chemistry-based approach that can be used not only to visualize the cancer tissue but also to distinguish morphology of the resected tissue only within a few minutes. It has a potential clinical application for breast-conserving surgery. Furthermore, the ability to perform chemical reactions with cancer metabolites only at the desired cancer site is highly advantageous for cancer therapy.

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Section: Introductionmentioning

confidence: 99%

Methods for Acrolein Detection: Recent Advances and Applications

Pradipta

Tanaka

2020

J. Idn. Chem. Soc.

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“…3,9-Diazabicyclo[3.3.1]nonanes showed the 5-HT3 receptor antagonist [21] and opioid δ and μ-receptor activities [22,23]. Triazabicyclo[3.3.1]nonane derivatives such as 2,6,9- and 3,7,9-triazabicyclo[3.3.1]nonanes [24,25,26,27,28] were synthesized from dimerization of α,β-unsaturated carbonyl compounds with alkylamines. Some 1,3,5,7-tetraazabicyclo[3.3.1]nonane derivatives have antithrombotic activities [29].…”

Section: Introductionmentioning

confidence: 99%

“…Some 1,3,5,7-tetraazabicyclo[3.3.1]nonane derivatives have antithrombotic activities [29]. Although tremendous progress has been achieved in the synthesis of mono-, di-, and tri-azabicyclo[3.3.1]nonanes [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27], the synthesis of tetra- and penta-azabicyclo[3.3.1]nonane frameworks has rarely been disclosed in the literature [30,31,32,33].…”

Section: Introductionmentioning

confidence: 99%

Facile Assembling of Novel 2,3,6,7,9-pentaazabicyclo- [3.3.1]nona-3,7-diene Derivatives under Microwave and Ultrasound Platforms

et al. 2019

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Reactions of a series of 3-oxo-2-arylhydrazonopropanal derivatives with two molar ratio of ammonium acetate afforded a library of tetrasubstituted 2,3,6,7,9-pentaazabicyclo[3.3.1]nona- 3,7-diene derivatives in good to excellent isolated yields. The reaction was activated with triethylamine catalyst under three different heating modes: thermal, ultrasonic and microwave irradiating conditions in ethanol solvent. The structures of the isolated products were fully characterized by spectral and analytical data as well as X-ray single crystal of selected examples.

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“…Acrolein exogenously or endogenously generated from oxidatively stressed cells could be directly visualized by simply treating cells with a fluorescent-azide probe. Alternatively, it has been known to diagnosis acrolein related diseases through detections of acrolein-amine conjugates615161718192021222324 such as 3-formyl-3,4-dehydropiperidine (or FDP; see 1 in Fig. 1A).…”

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A Reduction-Based Sensor for Acrolein Conjugates with the Inexpensive Nitrobenzene as an Alternative to Monoclonal Antibody

Takamatsu

Fukase

Oka

et al. 2016

Sci Rep

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Acrolein, a highly toxic α, β–unsaturated aldehyde, has been a longstanding key biomarker associated with a range of disorders related to oxidative stresses. One of the most promising methods for detecting acrolein involves the use of antibodies that can recognize the acrolein–lysine conjugate, 3-formyl-3, 4-dehydropiperidines (FDP), within oxidatively stressed cells and tissues from various disease states. We have uncovered here that FDP could reduce nitroarenes in high yields at 100 °C in the presence of excess CaCl2 as a Lewis acid promoter. This unique transformation allowed for the development of a de novo method for detecting levels of FDPs generated from proteins in urine or blood serum samples. Thus we successfully converted a non-fluorescent and inexpensive 4-nitrophthalonitrile probe to the corresponding fluorescent aniline, thereby constituting the concept of fluorescent switching. Its sensitivity level (0.84 nmol/mL) is more than that of ELISA assays (3.13 nmol/mL) and is already equally reliable and reproducible at this early stage of development. More importantly, this method is cost effective and simple to operate, requiring only mixing of samples with a kit solution. Our method thus possesses potential as a future alternative to the more costly and operatively encumbered conventional antibody-based methods.

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Exclusive formation of imino[4 + 4]cycloaddition products with biologically relevant amines: plausible candidates for acrolein biomarkers and biofunctional modulators

Abstract: We synthetically demonstrate that eight-membered heterocycles are the exclusive products of the reaction of acrolein with biologically relevant amines via an imino[4 + 4]cycloaddition.

Cited by 21 publications

References 48 publications

Methods for Acrolein Detection: Recent Advances and Applications

Methods for Acrolein Detection: Recent Advances and Applications

Facile Assembling of Novel 2,3,6,7,9-pentaazabicyclo- [3.3.1]nona-3,7-diene Derivatives under Microwave and Ultrasound Platforms

A Reduction-Based Sensor for Acrolein Conjugates with the Inexpensive Nitrobenzene as an Alternative to Monoclonal Antibody

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