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Synthesis, Structural Analysis, and Biological Evaluation of Novel ((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl Derivatives

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  • Biomedical Engineering
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Abstract

The objective of this study was to evaluate the synthesis, structural analysis, and biological effects of novel ((2, 4-dioxothiazolidin-5-ylidene)methyl)phenyl derivatives. The efficacy of 15-PGDH inhibition increased for the substituents in the derivatives in the order: cyclohexylpropyl > cyclohexylethyl > cyclohexylmethyl > cyclohexyl. Compound 12 inhibited 15-PGDH activity by binding to the amino acids Ile 214, Ile 210, Ile 194, Gln 148, and Leu 191 of 15-PGDH. Compounds 4, 22, and 23 produced the highest increment in PGE2 concentration, which was 122.19, 100.14, and 206.80%, respectively, compared to that of the control. Also, compounds 38 and 39, in which the central phenyl ring and the 2, 4-thiazolidinedione moiety were linked by a single bond, produced a relatively high increment in PGE2 concentration, which was 106.81 and 118.66%, respectively, compared to that of the control. The wound closure rates of compounds 22 and 39 were the highest, being 247.56 and 202.42%, respectively, compared to that of the positive control. Therefore, compounds 22 and 39 could not only efficiently regulate PGE2 concentration, but also induce cellular regeneration, and are expected to effectively treat a variety of diseases resulting from PGE2 deficiency.

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Acknowledgements

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2016R1D1A1B04930255).

The authors declare no conflict of interest.

Neither ethical approval nor informed consent was required for this study.

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Authors and Affiliations

  1. Department of Polymer Science & Engineering, Chosun University, Gwangju, 61452, Korea

    A Ri Na & Hoon Cho

  2. Biotechnology Laboratory, B-K Company Ltd, Jeonbuk, 5703, Korea

    Dubok Choi

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Correspondence to Dubok Choi or Hoon Cho.

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Na, A.R., Choi, D. & Cho, H. Synthesis, Structural Analysis, and Biological Evaluation of Novel ((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl Derivatives. Biotechnol Bioproc E 25, 149–163 (2020). https://doi.org/10.1007/s12257-019-0308-y

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