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

MicroRNAs (miRNAs) modulate the expression of over 30 % of mammalian genes during development and apoptosis, and abnormal expression of miRNAs may lead to a range of human pathologies. Therefore, analysis of miRNAs is valuable for disease diagnostics. In this work, a novel one‐pot fluorescence deriv...

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Published inChemistry : a European journal Vol. 26; no. 25; pp. 5639 - 5647
Main Authors Pan, Li, Zhang, Huaisheng, Zhao, Jingjin, Ogungbe, Ifedayo Victor, Zhao, Shulin, Liu, Yi‐Ming
Format Journal Article
LanguageEnglish
Published Germany Wiley Subscription Services, Inc 04.05.2020
Subjects
Acetaldehyde - analogs & derivatives
Acetaldehyde - chemistry
Adenine
Adenine - chemistry
Apoptosis
Chemistry
Chloroacetaldehyde
Chromatography
Chromatography, High Pressure Liquid - methods
dyes/pigments
Fluorescence
Fluorescence spectroscopy
Gene expression
High performance liquid chromatography
Humans
Liquid chromatography
magnetic properties
Mass Spectrometry
Mass spectroscopy
MicroRNAs
MicroRNAs - analysis
miRNA
Nucleic acids
RNA recognition
Spectrometry, Fluorescence - methods
Strategy
synthetic methods
Water
dyes/pigments
RNA recognition
fluorescence spectroscopy
magnetic properties
synthetic methods
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Abstract MicroRNAs (miRNAs) modulate the expression of over 30 % of mammalian genes during development and apoptosis, and abnormal expression of miRNAs may lead to a range of human pathologies. Therefore, analysis of miRNAs is valuable for disease diagnostics. In this work, a novel one‐pot fluorescence derivatization strategy was developed for miRNA analysis. The mechanism of the derivatization reaction was explored by using instrumental methods, including liquid chromatography, fluorescence spectroscopy, and mass spectrometry. Highly fluorescent N6‐ethenoadenine (ϵ‐adenine) was formed and detached from the miRNA sequence through the reaction of adenine in nucleic acids with 2‐chloroacetaldehyde (CAA) at 100 °C. This is the first experimental evidence that the cooperation of formed ϵ‐adenine and water‐mediated hydrogen‐bond interaction between the proton at the 2′‐ and the oxyanion at 3′‐positions stabilized the oxocarbenium significantly, which makes the depurination and derivatization of miRNA highly effective. Based on this derivatization strategy, a facile and sensitive high‐performance liquid chromatography method was developed for quantitative assay of miRNAs. In combination with magnetic solid‐phase extraction (MSPE), the HPLC method was shown to be useful for the determination of microRNAs at sub‐picomolar level in serum samples. microRNAs made easy: A one‐pot fluorescence derivatization strategy has been developed for highly sensitive microRNA analysis. Based on this derivatization strategy, a facile and sensitive high‐performance liquid chromatography method was developed for quantitative assay of microRNAs.
AbstractList MicroRNAs (miRNAs) modulate the expression of over 30 % of mammalian genes during development and apoptosis, and abnormal expression of miRNAs may lead to a range of human pathologies. Therefore, analysis of miRNAs is valuable for disease diagnostics. In this work, a novel one-pot fluorescence derivatization strategy was developed for miRNA analysis. The mechanism of the derivatization reaction was explored by using instrumental methods, including liquid chromatography, fluorescence spectroscopy, and mass spectrometry. Highly fluorescent N6 -ethenoadenine (ϵ-adenine) was formed and detached from the miRNA sequence through the reaction of adenine in nucleic acids with 2-chloroacetaldehyde (CAA) at 100 °C. This is the first experimental evidence that the cooperation of formed ϵ-adenine and water-mediated hydrogen-bond interaction between the proton at the 2'- and the oxyanion at 3'-positions stabilized the oxocarbenium significantly, which makes the depurination and derivatization of miRNA highly effective. Based on this derivatization strategy, a facile and sensitive high-performance liquid chromatography method was developed for quantitative assay of miRNAs. In combination with magnetic solid-phase extraction (MSPE), the HPLC method was shown to be useful for the determination of microRNAs at sub-picomolar level in serum samples.MicroRNAs (miRNAs) modulate the expression of over 30 % of mammalian genes during development and apoptosis, and abnormal expression of miRNAs may lead to a range of human pathologies. Therefore, analysis of miRNAs is valuable for disease diagnostics. In this work, a novel one-pot fluorescence derivatization strategy was developed for miRNA analysis. The mechanism of the derivatization reaction was explored by using instrumental methods, including liquid chromatography, fluorescence spectroscopy, and mass spectrometry. Highly fluorescent N6 -ethenoadenine (ϵ-adenine) was formed and detached from the miRNA sequence through the reaction of adenine in nucleic acids with 2-chloroacetaldehyde (CAA) at 100 °C. This is the first experimental evidence that the cooperation of formed ϵ-adenine and water-mediated hydrogen-bond interaction between the proton at the 2'- and the oxyanion at 3'-positions stabilized the oxocarbenium significantly, which makes the depurination and derivatization of miRNA highly effective. Based on this derivatization strategy, a facile and sensitive high-performance liquid chromatography method was developed for quantitative assay of miRNAs. In combination with magnetic solid-phase extraction (MSPE), the HPLC method was shown to be useful for the determination of microRNAs at sub-picomolar level in serum samples.
MicroRNAs (miRNAs) modulate the expression of over 30 % of mammalian genes during development and apoptosis, and abnormal expression of miRNAs may lead to a range of human pathologies. Therefore, analysis of miRNAs is valuable for disease diagnostics. In this work, a novel one‐pot fluorescence derivatization strategy was developed for miRNA analysis. The mechanism of the derivatization reaction was explored by using instrumental methods, including liquid chromatography, fluorescence spectroscopy, and mass spectrometry. Highly fluorescent N6‐ethenoadenine (ϵ‐adenine) was formed and detached from the miRNA sequence through the reaction of adenine in nucleic acids with 2‐chloroacetaldehyde (CAA) at 100 °C. This is the first experimental evidence that the cooperation of formed ϵ‐adenine and water‐mediated hydrogen‐bond interaction between the proton at the 2′‐ and the oxyanion at 3′‐positions stabilized the oxocarbenium significantly, which makes the depurination and derivatization of miRNA highly effective. Based on this derivatization strategy, a facile and sensitive high‐performance liquid chromatography method was developed for quantitative assay of miRNAs. In combination with magnetic solid‐phase extraction (MSPE), the HPLC method was shown to be useful for the determination of microRNAs at sub‐picomolar level in serum samples.
MicroRNAs (miRNAs) modulate the expression of over 30 % of mammalian genes during development and apoptosis, and abnormal expression of miRNAs may lead to a range of human pathologies. Therefore, analysis of miRNAs is valuable for disease diagnostics. In this work, a novel one-pot fluorescence derivatization strategy was developed for miRNA analysis. The mechanism of the derivatization reaction was explored by using instrumental methods, including liquid chromatography, fluorescence spectroscopy, and mass spectrometry. Highly fluorescent N -ethenoadenine (ϵ-adenine) was formed and detached from the miRNA sequence through the reaction of adenine in nucleic acids with 2-chloroacetaldehyde (CAA) at 100 °C. This is the first experimental evidence that the cooperation of formed ϵ-adenine and water-mediated hydrogen-bond interaction between the proton at the 2'- and the oxyanion at 3'-positions stabilized the oxocarbenium significantly, which makes the depurination and derivatization of miRNA highly effective. Based on this derivatization strategy, a facile and sensitive high-performance liquid chromatography method was developed for quantitative assay of miRNAs. In combination with magnetic solid-phase extraction (MSPE), the HPLC method was shown to be useful for the determination of microRNAs at sub-picomolar level in serum samples.
MicroRNAs (miRNAs) modulate the expression of over 30 % of mammalian genes during development and apoptosis, and abnormal expression of miRNAs may lead to a range of human pathologies. Therefore, analysis of miRNAs is valuable for disease diagnostics. In this work, a novel one‐pot fluorescence derivatization strategy was developed for miRNA analysis. The mechanism of the derivatization reaction was explored by using instrumental methods, including liquid chromatography, fluorescence spectroscopy, and mass spectrometry. Highly fluorescent N 6 ‐ethenoadenine (ϵ‐adenine) was formed and detached from the miRNA sequence through the reaction of adenine in nucleic acids with 2‐chloroacetaldehyde (CAA) at 100 °C. This is the first experimental evidence that the cooperation of formed ϵ‐adenine and water‐mediated hydrogen‐bond interaction between the proton at the 2′‐ and the oxyanion at 3′‐positions stabilized the oxocarbenium significantly, which makes the depurination and derivatization of miRNA highly effective. Based on this derivatization strategy, a facile and sensitive high‐performance liquid chromatography method was developed for quantitative assay of miRNAs. In combination with magnetic solid‐phase extraction (MSPE), the HPLC method was shown to be useful for the determination of microRNAs at sub‐picomolar level in serum samples.
MicroRNAs (miRNAs) modulate the expression of over 30 % of mammalian genes during development and apoptosis, and abnormal expression of miRNAs may lead to a range of human pathologies. Therefore, analysis of miRNAs is valuable for disease diagnostics. In this work, a novel one‐pot fluorescence derivatization strategy was developed for miRNA analysis. The mechanism of the derivatization reaction was explored by using instrumental methods, including liquid chromatography, fluorescence spectroscopy, and mass spectrometry. Highly fluorescent N6‐ethenoadenine (ϵ‐adenine) was formed and detached from the miRNA sequence through the reaction of adenine in nucleic acids with 2‐chloroacetaldehyde (CAA) at 100 °C. This is the first experimental evidence that the cooperation of formed ϵ‐adenine and water‐mediated hydrogen‐bond interaction between the proton at the 2′‐ and the oxyanion at 3′‐positions stabilized the oxocarbenium significantly, which makes the depurination and derivatization of miRNA highly effective. Based on this derivatization strategy, a facile and sensitive high‐performance liquid chromatography method was developed for quantitative assay of miRNAs. In combination with magnetic solid‐phase extraction (MSPE), the HPLC method was shown to be useful for the determination of microRNAs at sub‐picomolar level in serum samples. microRNAs made easy: A one‐pot fluorescence derivatization strategy has been developed for highly sensitive microRNA analysis. Based on this derivatization strategy, a facile and sensitive high‐performance liquid chromatography method was developed for quantitative assay of microRNAs.
Author Liu, Yi‐Ming
Zhang, Huaisheng
Zhao, Jingjin
Zhao, Shulin
Ogungbe, Ifedayo Victor
Pan, Li
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RNA recognition
fluorescence spectroscopy
magnetic properties
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Snippet MicroRNAs (miRNAs) modulate the expression of over 30 % of mammalian genes during development and apoptosis, and abnormal expression of miRNAs may lead to a...
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SubjectTerms Acetaldehyde - analogs & derivatives
Acetaldehyde - chemistry
Adenine
Adenine - chemistry
Apoptosis
Chemistry
Chloroacetaldehyde
Chromatography
Chromatography, High Pressure Liquid - methods
dyes/pigments
Fluorescence
Fluorescence spectroscopy
Gene expression
High performance liquid chromatography
Humans
Liquid chromatography
magnetic properties
Mass Spectrometry
Mass spectroscopy
MicroRNAs
MicroRNAs - analysis
miRNA
Nucleic acids
RNA recognition
Spectrometry, Fluorescence - methods
Strategy
synthetic methods
Water
Title A New One‐Pot Fluorescence Derivatization Strategy for Highly Sensitive MicroRNA Analysis
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.201905639
https://www.ncbi.nlm.nih.gov/pubmed/31953882
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Volume 26
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