Base-Modified Nucleosides: Etheno Derivatives

Jahnz‐Wechmann, Zofia; Framski, Grzegorz; Januszczyk, Piotr; Boryski, Jerzy

doi:10.3389/fchem.2016.00019

Cited by 28 publications

(21 citation statements)

References 66 publications

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“…The uracil base cannot be derivatized by CAA . However, the fluorescence produced by ϵ‐cytosine is too weak to be used for quantification . Therefore, the excitation‐emission spectra of ϵ‐adenine and ϵ‐guanine were investigated.…”

Section: Resultsmentioning

confidence: 99%

A New One‐Pot Fluorescence Derivatization Strategy for Highly Sensitive MicroRNA Analysis

Zhang

Zhao

et al. 2020

Chemistry A European J

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MicroRNAs (miRNAs)m odulate the expression of over 30 %o fm ammalian genes during development and apoptosis, and abnormale xpression of miRNAs may lead to arange of humanp athologies. Therefore, analysis of miRNAs is valuable for disease diagnostics. In this work, an ovel onepot fluorescence derivatization strategy wasd eveloped for miRNA analysis. The mechanism of the derivatization reaction was explored by using instrumental methods, including liquid chromatography,f luorescence spectroscopy,a nd mass spectrometry.H ighly fluorescent N 6 -ethenoadenine (e-adenine) was formed and detached from the miRNA sequence through the reaction of adenine in nucleic acids with 2-chloroacetaldehyde (CAA) at 100 8C. This is the first experimental evidence that the cooperation of formed e-adenine and water-mediatedh ydrogen-bond interaction between the protona tt he 2'-a nd the oxyanion at 3'-positions stabilized the oxocarbenium significantly,w hich makes the depurinationa nd derivatization of miRNA highly effective. Based on this derivatization strategy,afacile and sensitive highperformancel iquid chromatography method was developed for quantitative assay of miRNAs. In combination with magnetic solid-phase extraction( MSPE), the HPLCm ethod was shown to be useful for the determination of microRNAsa t sub-picomolar level in serum samples.[a] Dr.

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Section: Resultsmentioning

confidence: 99%

A New One‐Pot Fluorescence Derivatization Strategy for Highly Sensitive MicroRNA Analysis

Zhang

Zhao

et al. 2020

Chemistry A European J

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“…We have shown that 2-aminopurine easily reacts with aqueous chloroacetaldehyde to give two fluorescent, isomeric products 1 and 2. Both products are substrates for the bacterial (E. coli) purine nucleoside phosphorylase, but in both cases the ribosylation site has been found to be N 2 rather than N 9 . The new ribosides are fluorescent and potentially useful as fluorescent probes.…”

Section: Discussionmentioning

confidence: 99%

“…Tri-cyclic nucleosides and nucleotides are also utilized as dimensional probes for enzymatic studies [5,6]. Some of the tri-cyclic analogs and their derivatives reveal promising anti-viral properties [7], recently reviewed by Janz-Wechmann et al [8,9]. They are known to reveal substrate or inhibitory activities towards many enzymes of purine metabolism [2], and they are important intermediates in the process of chemical mutagenesis [10,11].…”

Section: Introductionmentioning

confidence: 99%

Tricyclic Nucleobase Analogs and Their Ribosides as Substrates and Inhibitors of Purine-Nucleoside Phosphorylases III. Aminopurine Derivatives

Stachelska-Wierzchowska

Wierzchowski

Górka

et al. 2020

Molecules

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Etheno-derivatives of 2-aminopurine, 2-aminopurine riboside, and 7-deazaadenosine (tubercidine) were prepared and purified using standard methods. 2-Aminopurine reacted with aqueous chloroacetaldehyde to give two products, both exhibiting substrate activity towards bacterial (E. coli) purine-nucleoside phosphorylase (PNP) in the reverse (synthetic) pathway. The major product of the chemical synthesis, identified as 1,N2-etheno-2-aminopurine, reacted slowly, while the second, minor, but highly fluorescent product, reacted rapidly. NMR analysis allowed identification of the minor product as N2,3-etheno-2-aminopurine, and its ribosylation product as N2,3-etheno-2-aminopurine-N2-β-d-riboside. Ribosylation of 1,N2-etheno-2-aminopurine led to analogous N2-β-d-riboside of this base. Both enzymatically produced ribosides were readily phosphorolysed by bacterial PNP to the respective bases. The reaction of 2-aminopurine-N9-β -d-riboside with chloroacetaldehyde gave one major product, clearly distinct from that obtained from the enzymatic synthesis, which was not a substrate for PNP. A tri-cyclic 7-deazaadenosine (tubercidine) derivative was prepared in an analogous way and shown to be an effective inhibitor of the E. coli, but not of the mammalian enzyme. Fluorescent complexes of amino-purine analogs with E. coli PNP were observed.

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“…In the same period, the synthesis of novel nucleoside analogues compounds were published, using guanosine as precursor [75]. First, halogen atom was incorporated at the 2-position of this base purine.…”

Section: Methods Of Synthesis Of Adenosine Derivatives Interaction Wmentioning

confidence: 99%

Adenosine: Synthetic Methods of Its Derivatives and Antitumor Activity

Valdés

Luna

Arévalo

et al. 2018

MRMC

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Since 1929, several researchers have conducted studies in relation to the nucleoside of adenosine (1) mainly distribution identifying, characterizing their biological importance and synthetic chemistry to which this type of molecule has been subjected to obtain multiple of its derivatives. The receptors that interact with adenosine and its derivatives, called purinergic receptors, are classified as A1, A2A, A2B and A3. In the presence of agonists and antagonists, these receptors are involved in various physiological processes and diseases. This review describes and compares some of the synthetic methods that have been developed over the last 30 years for obtaining some adenosine derivatives, classified according to substitution processes, complexation, mating and conjugation. Finally, we mention that although the concentrations of these nucleosides are low in normal tissues, they can increase rapidly in pathophysiological conditions such as hypoxia, ischemia, inflammation, trauma and cancer. In particular, the evaluation of adenosine derivatives as adjunctive therapy promises to have a significant impact on the treatment of certain cancers, although the transfer of these results to clinical practice requires a deeper understanding of how adenosine regulates the process of tumorigenesis.

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Base-Modified Nucleosides: Etheno Derivatives

Cited by 28 publications

References 66 publications

A New One‐Pot Fluorescence Derivatization Strategy for Highly Sensitive MicroRNA Analysis

A New One‐Pot Fluorescence Derivatization Strategy for Highly Sensitive MicroRNA Analysis

Tricyclic Nucleobase Analogs and Their Ribosides as Substrates and Inhibitors of Purine-Nucleoside Phosphorylases III. Aminopurine Derivatives

Adenosine: Synthetic Methods of Its Derivatives and Antitumor Activity

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