Binding of a Pyrene-Based Fluorescent Amyloid Ligand to Transthyretin: A Combined Crystallographic and Molecular Dynamics Study Article Swipe
Nghia Nguyen Thi Minh
,
A. Begum
,
Jun Zhang
,
Petter Leira
,
Yogesh Todarwal
,
Mathieu Linares
,
Patrick Norman
,
Dean Derbyshire
,
Eleonore von Castelmur
,
Mikaël Lindgren
,
Per Hammarström
,
Carolin König
·
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.1021/acs.jpcb.3c02147
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.1021/acs.jpcb.3c02147
Misfolding and aggregation of transthyretin (TTR) cause several amyloid diseases. Besides being an amyloidogenic protein, TTR has an affinity for bicyclic small-molecule ligands in its thyroxine (T4) binding site. One class of TTR ligands are trans-stilbenes. The trans-stilbene scaffold is also widely applied for amyloid fibril-specific ligands used as fluorescence probes and as positron emission tomography tracers for amyloid detection and diagnosis of amyloidosis. We have shown that native tetrameric TTR binds to amyloid ligands based on the trans-stilbene scaffold providing a platform for the determination of high-resolution structures of these important molecules bound to protein. In this study, we provide spectroscopic evidence of binding and X-ray crystallographic structure data on tetrameric TTR complex with the fluorescent salicylic acid-based pyrene amyloid ligand (Py1SA), an analogue of the Congo red analogue X-34. The ambiguous electron density from the X-ray diffraction, however, did not permit Py1SA placement with enough confidence likely due to partial ligand occupancy. Instead, the preferred orientation of the Py1SA ligand in the binding pocket was determined by molecular dynamics and umbrella sampling approaches. We find a distinct preference for the binding modes with the salicylic acid group pointing into the pocket and the pyrene moiety outward to the opening of the T4 binding site. Our work provides insight into TTR binding mode preference for trans-stilbene salicylic acid derivatives as well as a framework for determining structures of TTR-ligand complexes.
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/acs.jpcb.3c02147
- OA Status
- hybrid
- Cited By
- 3
- References
- 44
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4384922258
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4384922258Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1021/acs.jpcb.3c02147Digital Object Identifier
- Title
-
Binding of a Pyrene-Based Fluorescent Amyloid Ligand to Transthyretin: A Combined Crystallographic and Molecular Dynamics StudyWork title
- Type
-
articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2023Year of publication
- Publication date
-
2023-07-21Full publication date if available
- Authors
-
Nghia Nguyen Thi Minh, A. Begum, Jun Zhang, Petter Leira, Yogesh Todarwal, Mathieu Linares, Patrick Norman, Dean Derbyshire, Eleonore von Castelmur, Mikaël Lindgren, Per Hammarström, Carolin KönigList of authors in order
- Landing page
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https://doi.org/10.1021/acs.jpcb.3c02147Publisher landing page
- Open access
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YesWhether a free full text is available
- OA status
-
hybridOpen access status per OpenAlex
- OA URL
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https://doi.org/10.1021/acs.jpcb.3c02147Direct OA link when available
- Concepts
-
Chemistry, Ligand (biochemistry), Transthyretin, Amyloid (mycology), Fluorescence, Small molecule, Pyrene, Stereochemistry, Moiety, Crystallography, Biochemistry, Biology, Organic chemistry, Receptor, Inorganic chemistry, Quantum mechanics, Physics, EndocrinologyTop concepts (fields/topics) attached by OpenAlex
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-
3Total citation count in OpenAlex
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2024: 2, 2023: 1Per-year citation counts (last 5 years)
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44Number of works referenced by this work
- Related works (count)
-
10Other works algorithmically related by OpenAlex
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