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The use of multicomponent reactions in the development of bis-boronic acids for the detection of ß-sialic acid.
Chou, Tzu-Ching; Hu, Ying-Li; Xie, Guan-Cheng; Jiang, Jyh-Chiang; Peng, Liang-Ying; Tsai, Hsiao-Chun; Yao, Chiao-Tien; Tsai, Yi-Jie; Huang, Ting-Yu; Hu, Jing-Wen; Chen, Yi-Ching; Tsai, Min-Yeh; Chen, Yi-Wei; Pan, Po-Shen.
Affiliation
  • Chou TC; Department of Chemistry, Tamkang University, No. 151, Yingzhuan Rd., New Taipei City, Tamsui Dist., Taiwan. 138020@gms.tku.edu.tw.
  • Hu YL; Department of Chemical Engineering, National Taiwan University of Science and Technology, Taipei, Taiwan.
  • Xie GC; Department of Chemical Engineering, National Taiwan University of Science and Technology, Taipei, Taiwan.
  • Jiang JC; Department of Chemical Engineering, National Taiwan University of Science and Technology, Taipei, Taiwan.
  • Peng LY; Department of Chemistry, Tamkang University, No. 151, Yingzhuan Rd., New Taipei City, Tamsui Dist., Taiwan. 138020@gms.tku.edu.tw.
  • Tsai HC; Department of Chemistry, Tamkang University, No. 151, Yingzhuan Rd., New Taipei City, Tamsui Dist., Taiwan. 138020@gms.tku.edu.tw.
  • Yao CT; Department of Chemistry, Tamkang University, No. 151, Yingzhuan Rd., New Taipei City, Tamsui Dist., Taiwan. 138020@gms.tku.edu.tw.
  • Tsai YJ; Department of Chemistry, Tamkang University, No. 151, Yingzhuan Rd., New Taipei City, Tamsui Dist., Taiwan. 138020@gms.tku.edu.tw.
  • Huang TY; Department of Chemistry, Tamkang University, No. 151, Yingzhuan Rd., New Taipei City, Tamsui Dist., Taiwan. 138020@gms.tku.edu.tw.
  • Hu JW; Department of Chemistry, Tamkang University, No. 151, Yingzhuan Rd., New Taipei City, Tamsui Dist., Taiwan. 138020@gms.tku.edu.tw.
  • Chen YC; Department of Chemistry, Tamkang University, No. 151, Yingzhuan Rd., New Taipei City, Tamsui Dist., Taiwan. 138020@gms.tku.edu.tw.
  • Tsai MY; Department of Chemistry and Biochemistry, National Chung Cheng University, Minhsiung, Taiwan.
  • Chen YW; Department of Oncology, Taipei Veterans General Hospital, Taipei, Taiwan.
  • Pan PS; Department of Chemistry, Tamkang University, No. 151, Yingzhuan Rd., New Taipei City, Tamsui Dist., Taiwan. 138020@gms.tku.edu.tw.
Org Biomol Chem ; 22(8): 1639-1645, 2024 02 21.
Article in En | MEDLINE | ID: mdl-38180439
ABSTRACT
Sialic acid (SA) is a naturally occurring monosaccharide found in glycoproteins and glycolipids. Changes in the expression of SA are associated with several diseases; thus, the detection of SA is of great significance for biological research, cancer diagnosis, and treatment. Boronic acid analogs have emerged as a promising tool for detecting sugars such as SA due to its reversible covalent bonding ability. In this study, 11 bis-boronic acid compounds and 2 mono-boronic acid compounds were synthesized via a highly efficient Ugi-4CR strategy. The synthesized compounds were subjected to affinity fluorescence binding experiments to evaluate their binding capability to SA. Compound A1 was shown to have a promising binding constant of 2602 ± 100 M-1 at pH = 6.0. Density Functional Theory (DFT) calculations examining the binding modes between A1 and SA indicated that the position of the boronic acid functional group was strongly correlated with its interaction with SA's α-hydroxy acid unit. The DFT calculations were consistent with the observations from the fluorescence experiments, demonstrating that the number and relative positions of the boronic acid functional groups are critical factors in enhancing the binding affinity to SA. DFT calculations of both S and R configuration of A1 indicated that the effect of the S/R configuration of A1 on its binding with ß-sialic acid was insignificant as the Ugi-4CR generated racemic products. A fluorine atom was incorporated into the R2 substituent of A1 as an electron-withdrawing group to produce A5, which possessed a significantly higher capability to bind to SA (Keq = 7015 ± 5 M-1 at pH = 6.0). Finally, A1 and A5 were shown to possess exceptional binding selectivity toward ß-sialic acid under pH of 6.0 and 6.5 while preferring to bind with glucose, fructose, and galactose under pH of 7.0 and 7.5.
Subject(s)

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Boronic Acids / N-Acetylneuraminic Acid Type of study: Diagnostic_studies Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2024 Document type: Article Affiliation country:

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Boronic Acids / N-Acetylneuraminic Acid Type of study: Diagnostic_studies Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2024 Document type: Article Affiliation country: