Discovery of Novel Pyrazole-Based Selective Aldosterone Synthase (CYP11B2) Inhibitors: A New Template to Coordinate the Heme-Iron Motif of CYP11B2 Article Swipe
Ryo Sakakibara
,
Wataru Sasaki
,
Yuichi Onda
,
Minami Yamaguchi
,
Hideki Ushirogochi
,
Yuki Hiraga
,
Sato Kanako
,
Masashi Nishio
,
Yasuhiro Egi
,
Kei Takedomi
,
H. Shimizu
,
Tomoko Ohbora
,
Fumihiko Akahoshi
·
YOU?
·
· 2018
· Open Access
·
· DOI: https://doi.org/10.1021/acs.jmedchem.8b00328
YOU?
·
· 2018
· Open Access
·
· DOI: https://doi.org/10.1021/acs.jmedchem.8b00328
It is necessary for aldosterone synthase (CYP11B2) inhibitors to have both high potency and high selectivity over 11β-hydroxylase (CYP11B1), a critical enzyme for cortisol synthesis. Previous studies have reported a number of CYP11B2 inhibitors, most of which have an imidazole or pyridine ring to coordinate the heme-iron motif of CYP11B2; however, highly selective inhibitors of human CYP11B2 are still needed. To expand the selectivity in humans, we explored alternative templates and found that pyrazoles were suitable templates for CYP11B2 inhibitors. Investigation of pyrazoles, especially N-alkyl pyrazoles, as a new template to coordinate the heme-iron motif led to a potent and highly selective CYP11B2 inhibitor 28 with an aldosterone-lowering effect at 1 mg/kg dosing in cynomolgus monkeys.
Related Topics
Concepts
Aldosterone synthase
Chemistry
Heme
Steroid 11-beta-hydroxylase
Pyrazole
Hyperaldosteronism
Stereochemistry
Steroid
Aldosterone
Enzyme
Selectivity
Biochemistry
Renin–angiotensin system
Endocrinology
Biology
Blood pressure
Catalysis
Hormone
Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/acs.jmedchem.8b00328
- OA Status
- green
- Cited By
- 20
- References
- 49
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W2805975311
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
-
https://openalex.org/W2805975311Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.1021/acs.jmedchem.8b00328Digital Object Identifier
- Title
-
Discovery of Novel Pyrazole-Based Selective Aldosterone Synthase (CYP11B2) Inhibitors: A New Template to Coordinate the Heme-Iron Motif of CYP11B2Work title
- Type
-
articleOpenAlex work type
- Language
-
enPrimary language
- Publication year
-
2018Year of publication
- Publication date
-
2018-06-07Full publication date if available
- Authors
-
Ryo Sakakibara, Wataru Sasaki, Yuichi Onda, Minami Yamaguchi, Hideki Ushirogochi, Yuki Hiraga, Sato Kanako, Masashi Nishio, Yasuhiro Egi, Kei Takedomi, H. Shimizu, Tomoko Ohbora, Fumihiko AkahoshiList of authors in order
- Landing page
-
https://doi.org/10.1021/acs.jmedchem.8b00328Publisher landing page
- Open access
-
YesWhether a free full text is available
- OA status
-
greenOpen access status per OpenAlex
- OA URL
-
https://doi.org/10.7270/q2f47rn9Direct OA link when available
- Concepts
-
Aldosterone synthase, Chemistry, Heme, Steroid 11-beta-hydroxylase, Pyrazole, Hyperaldosteronism, Stereochemistry, Steroid, Aldosterone, Enzyme, Selectivity, Biochemistry, Renin–angiotensin system, Endocrinology, Biology, Blood pressure, Catalysis, HormoneTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
20Total citation count in OpenAlex
- Citations by year (recent)
-
2024: 2, 2023: 3, 2022: 1, 2021: 3, 2020: 7Per-year citation counts (last 5 years)
- References (count)
-
49Number of works referenced by this work
- Related works (count)
-
10Other works algorithmically related by OpenAlex
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