Structure–Activity Relationship and In Silico Evaluation of cis- and trans-PCPA-Derived Inhibitors of LSD1 and LSD2 Article Swipe
Hideaki Niwa
,
Chiduru Watanabe
,
Shin Sato
,
Toshiyuki Harada
,
Hisami Watanabe
,
Ryo Tabusa
,
Shunsuke Fukasawa
,
Ayane Shiobara
,
Tomoko Hashimoto
,
Osamu Ohno
,
Kana Nakamura
,
Keiko Tsuganezawa
,
Akiko Tanaka
,
Mikako Shirouzu
,
Teruki Honma
,
Kenji Matsuno
,
Takashi Umehara
·
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.1021/acsmedchemlett.2c00294
YOU?
·
· 2022
· Open Access
·
· DOI: https://doi.org/10.1021/acsmedchemlett.2c00294
trans-2-Phenylcycloproylamine (trans-PCPA) has been used as the scaffold to develop covalent-binding inhibitors against lysine-specific demethylase 1 (LSD1/KDM1A), a therapeutic target for several cancers. However, the effects of different structural moieties on the inhibitory activity, selectivity, and reactivity of these derivatives, including the cis isomers, against LSD1 and its paralogue LSD2/KDM1B are not fully understood. Here we synthesized 65 cis- and trans-PCPA derivatives and evaluated their inhibitory activity against LSD1 and LSD2. One of the derivatives, 7c (cis-4-Br-2,5-F2-PCPA; S1024), inhibited LSD1 and LSD2 with K i values of 0.094 μM and 8.4 μM, respectively, and increased the level of dimethylated histone H3 at K4 in CCRF-CEM cells. A machine learning-based regression model (Q 2 = 0.61) to predict LSD1-inhibitory activity was also constructed and showed a good prediction accuracy (R 2 = 0.81) for 12 test-set compounds, including 7c. The present methodology would be useful when designing covalent-binding inhibitors for other enzymes.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/acsmedchemlett.2c00294
- https://pubs.acs.org/doi/pdf/10.1021/acsmedchemlett.2c00294
- OA Status
- bronze
- Cited By
- 15
- References
- 25
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4293069267
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Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4293069267Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.1021/acsmedchemlett.2c00294Digital Object Identifier
- Title
-
Structure–Activity Relationship and In Silico Evaluation of cis- and trans-PCPA-Derived Inhibitors of LSD1 and LSD2Work title
- Type
-
articleOpenAlex work type
- Language
-
enPrimary language
- Publication year
-
2022Year of publication
- Publication date
-
2022-08-18Full publication date if available
- Authors
-
Hideaki Niwa, Chiduru Watanabe, Shin Sato, Toshiyuki Harada, Hisami Watanabe, Ryo Tabusa, Shunsuke Fukasawa, Ayane Shiobara, Tomoko Hashimoto, Osamu Ohno, Kana Nakamura, Keiko Tsuganezawa, Akiko Tanaka, Mikako Shirouzu, Teruki Honma, Kenji Matsuno, Takashi UmeharaList of authors in order
- Landing page
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https://doi.org/10.1021/acsmedchemlett.2c00294Publisher landing page
- PDF URL
-
https://pubs.acs.org/doi/pdf/10.1021/acsmedchemlett.2c00294Direct link to full text PDF
- Open access
-
YesWhether a free full text is available
- OA status
-
bronzeOpen access status per OpenAlex
- OA URL
-
https://pubs.acs.org/doi/pdf/10.1021/acsmedchemlett.2c00294Direct OA link when available
- Concepts
-
In silico, Demethylase, Chemistry, Histone, Stereochemistry, Lysine, Enzyme, Covalent bond, Computational biology, Biochemistry, Biology, Amino acid, Gene, Organic chemistryTop concepts (fields/topics) attached by OpenAlex
- Cited by
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15Total citation count in OpenAlex
- Citations by year (recent)
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2025: 3, 2024: 2, 2023: 3, 2022: 7Per-year citation counts (last 5 years)
- References (count)
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25Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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