- Polarity-Tuning Derivatization-LC-MS Approach for Probing Global Carboxyl-Containing Metabolites in Colorectal Cancer
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Carboxyl-containing metabolites (CCMs) widely exist in living systems and are the essential components for life. Global characteristics of CCMs in biological samples are critical for the understanding of physiological processes and the discovery for the onset of relevant diseases. However, their determination represents a challenge due to enormous polarity differences, structural diversity, high structural similarity, and poor ionization efficiency in mass spectrometry. Herein, 5-(diisopropylamino)amylamine (DIAAA) derivatization coupled with liquid chromatography-mass spectrometry (LC-MS) was developed for mapping the CCMs. With this methodology, the sensitivity was significantly enhanced. More importantly, the hydrophobicity of polar CCMs, amino acids, TCA cycle intermediates, and short-chain fatty acids and the hydrophilicity of low-polar CCMs, long-chain fatty acids, and bile acids were significantly increased, resulting in a remarkable separation efficiency for which 68 CCMs can be simultaneously determined. Furthermore, the polarity-tuning effect was confirmed to be induced by the different impacts of aliphatic chains and nitrogen atom in DIAAA, the latter existing as a cation in the acidic mobile phase, using different derivatization reagents. Finally, this derivatization method was utilized to hunt for the potential biomarkers in colorectal cancer (CRC) patients and 52 CCMs, related with several key metabolic pathways, including amino acids metabolism, TCA cycle, fatty acid metabolism, pyruvate metabolism, and gut flora metabolism were identified. This innovative polarity-tuning derivatization-LC-MS approach was proved to be a valuable tool for probing global metabolome with high separation efficiency and sensitivity in various biological samples.
- Bian, Xiqing,Li, Na,Tan, Binbin,Sun, Baoqing,Guo, Ming-Quan,Huang, Guoxin,Fu, Li,Hsiao, W. L. Wendy,Liu, Liang,Wu, Jian-Lin
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p. 11210 - 11215
(2018/10/02)
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- Design of an organocatalyst for the enantioselective Diels-Alder reaction with α-acyloxyacroleins
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We have realized the first enantioselective organocatalytic Diels-Alder reaction between α-substituted acroleins, such as α-acyloxyacroleins, and not only cyclic but also acyclic dienes. α-Acyloxyacroleins are useful as synthetic equivalents of α-haloacro
- Ishihara, Kazuaki,Nakano, Kazuhiko
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p. 10504 - 10505
(2007/10/03)
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- Herbicidal imidazolones
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Compounds such as Formula I having herbicidal utility are disclosed: STR1 wherein Q is STR2 R1 is H; alkyl, haloalkyl or halogen R2 is C1 -C2 alkyl optionally substituted with one or more halogens, OR8, CN, COR9, CO2 R31 or CONR32 R33 ; CN; CO2 R34 ; CONR35 R36 ; S(O)n R8 ; S(O)n NR19 R8 or COR37 ; or R1 and R2 can be taken together along with the carbon to which they are attached to form C=CHCO2 R31 ; C=(CH3)CO2 R31 ; C=(C2 H5)CO2 R31 ; C=CHCONR32 R33 ; C=C(CH3)CONR32 R33 or C=C(C2 H5)CONR32 R33.
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