Etheno derivatives of adenine and cytosine (review)

Kost, A. A.; Ivanov, Mikhail

doi:10.1007/bf02401711

Cited by 14 publications

(12 citation statements)

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“…The reaction between adenine and CAA at pH values close to neutral to form the fluorescent ɛA has been extensively reviewed by Kost and Ivanov (1980). It is rapid, quantitative, and results in the addition of an imidazole ring, also known as an “ethylene bridge,” that links the ring nitrogen atom of adenine to the exocyclic amino group (Kochetkov and others 1971, 1972).…”

Section: Resultsmentioning

confidence: 99%

Validation of Immunodetection (ELISA) of Ricin Using a Biological Activity Assay

Lumor¹,

Hutt²,

Ronningen³

et al. 2011

Journal of Food Science

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The suitability of enzyme-linked immunosorbent assay (ELISA) for residual ricin toxicity determination was investigated in this study. Ricin was thermally treated at 80 to 90 °C for up to 9 min, and its residual concentration was determined by means of a commercial ELISA kit, and its bioactivity (amount of adenine released from DNA) was determined by means of a biological activity assay (BAA). Results showed that inactivation of ricin followed 1st-order kinetics. The half-life values for loss of bioactivity at 80, 85, and 90 °C were 1.93, 0.65, and 0.41 min, respectively. Similarly, the half-life values for reduction in ricin concentration determined by ELISA were 3.06, 0.79, and 0.43 min, respectively. The half-lives determined by both assays were only significantly different at 80 °C. The Z, Q(10), and Arrhenius activation energy values determined by both assays were dissimilar: 11.74 ˚C, 7.12 and 50.1 kcal/mol, respectively, by ELISA; and 14.87 °C, 4.71 and 39.5 kcal/mol, respectively, by BAA. Nevertheless, our findings indicate that the 2 assays were highly correlated (R(2) = 1), and it can be concluded that ELISA would be a reliable method for detecting residual toxicity of heat-treated ricin based on fraction lost. Practical Application: The results of this study indicate that immunodetection, even though not a direct measurement of the biological activity of ricin, is suitable for determining the residual bioactivity of ricin since immunodetection and the biological activity assay used in this investigation were highly correlated. Therefore, ELISA can be used for routine assessment of residual activity or toxicity of ricin in thermally treated foods.

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Section: Resultsmentioning

confidence: 99%

Validation of Immunodetection (ELISA) of Ricin Using a Biological Activity Assay

Lumor¹,

Hutt²,

Ronningen³

et al. 2011

Journal of Food Science

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“…The release of adenine from polynucleotides by RIPs has been reported (l, 2,5,14). In the present study, the adenine released by Stxl was reacted with chloroacetaldehyde to form the fluorescent sA (8)(9)(10), which was quantified and used as a measure of Stxl biological activity. Preliminary investigations revealed that Stxl was most active at pH values greater than 6.0 (data not shown) but lost significant activity at lower pH values.…”

Section: Resultsmentioning

confidence: 99%

Comparison of the Presence of Shiga Toxin 1 in Food Matrices as Determined by an Enzyme-Linked Immunosorbent Assay and a Biological Activity Assay

Lumor

Fredrickson

Ronningen

et al. 2012

Journal of Food Protection

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This study was conducted to compare the identification of Shiga toxin 1 (Stx1) based on its specific biological activity and based on results of a commercial enzyme-linked immunosorbent assay (ELISA) kit. Stx1 was thermally treated for various periods in phosphate-buffered saline, milk, and orange juice. The residual Stx1 concentration was determined with the commercial ELISA kit, and its residual enzymatic activity (amount of adenine released from a 2,551-bp DNA substrate) was determined with a biological activity assay (BAA). Regression analysis indicated that the inactivation of Stx1 as a function of time followed first-order kinetics. The half-lives determined at 60, 65, 70, 75, 80, and 85°C were 9.96, 3.19, 2.67, 0.72, 0.47, and 0.29 min, respectively, using the BAA. The half-lives determined by the ELISA with thermal treatments at 70, 75, 80, and 85°C were 40.47, 11.03, 3.64, and 1.40 min, respectively. The Z, Q(10), and Arrhenius activation energy values derived by both assays were dissimilar, indicating that the rate of inactivation of the active site of Stx1 was less sensitive to temperature change than was denaturation of the epitope(s) used in the ELISA. These values were 10.28°C and 9.40 and 54.70 kcal/mol, respectively, with the ELISA and 16°C and 4.11 and 34 kcal/mol, respectively, with the BAA. Orange juice enhanced Stx1 inactivation as a function of increasing temperature, whereas inactivation in 2% milk was not very much different from that in phosphate-buffered saline. Our investigation indicates that the ELISA would be a reliable method for detecting the residual toxicity of heat-treated Stx1 because the half-lives determined with the ELISA were greater than those determined with the BAA (faster degradation) at all temperatures and were highly correlated (R(2) = 0.994) with those determined with the BAA.

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“…The mechanism of the one‐pot reaction of microRNA with CAA can be described as follows. CAA is an electrophile reagent, the carbonyl group of which attacks the exocyclic 6‐amino group of adenosines of microRNA to initiate the condensation, leading to an unstable intermediate; the reaction is reversible. This intermediate then undergoes intramolecular cyclization to a stable intermediate, as a result of alkylation of the endocyclic N 1 ; this process is irreversible.…”

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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Etheno derivatives of adenine and cytosine (review)

Cited by 14 publications

References 50 publications

Validation of Immunodetection (ELISA) of Ricin Using a Biological Activity Assay

Validation of Immunodetection (ELISA) of Ricin Using a Biological Activity Assay

Comparison of the Presence of Shiga Toxin 1 in Food Matrices as Determined by an Enzyme-Linked Immunosorbent Assay and a Biological Activity Assay

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

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