Binding of the Respiratory Chain Inhibitor Antimycin to the Mitochondrial bc1 Complex: A New Crystal Structure Reveals an Altered Intramolecular Hydrogen-bonding Pattern
Open accessAbstract
Antimycin A (antimycin), one of the first known and most potent inhibitors of the mitochondrial respiratory chain, binds to the quinone reduction site of the cytochrome bc1 complex. Structure-activity relationship studies have shown that the N-formylamino-salicyl-amide group is responsible for most of the binding specificity, and suggested that a low pKa for the phenolic OH group and an intramolecular H-bond between that OH and the carbonyl O of the salicylamide linkage are important. Two previous X-ray structures of antimycin bound to vertebrate bc1 complex gave conflicting results. A new structure reported here of the bovine mitochondrial bc1 complex at 2.28 A resolution with antimycin bound, allows us for the first time to reliably describe the binding of antimycin and shows that the intramolecular hydrogen bond described in solution and in the small-molecule structure is replaced by one involving the NH rather than carbonyl O of the amide linkage, with rotation of the amide group relative to the aromatic ring. The phenolic OH and formylamino N form H-bonds with conserved Asp228 of cytochrome b, and the formylamino O H-bonds via a water molecule to Lys227. A strong density, the right size and shape for a diatomic molecule is found between the other side of the dilactone ring and the alphaA helix.
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Antimycin A binds to the quinone reduction site of complex III, inhibiting ubiquinol oxidation in the ETC.
“Antimycin A binds to the quinone reduction site of complex III, thereby inhibiting the oxidation of ubiquinol in the ETC51.”
From Stimulation of superoxide production increases fungicidal action of miconazole against Candida albicans biofilms (2016) · cites this paper as [51]
The Introduction (page unavailable) states that antimycin A binds the quinone-reduction (Qi) site of the mitochondrial bc1 complex and blocks the reaction there. It places quinol oxidation at the antimycin-insensitive Qo site, so the paper does not support the claim that antimycin directly inhibits that oxidation step. (LLM, conf=0.86)
Experimental — accuracy not yet measuredInhibition of mitochondrial complex I by rotenone or complex III by antimycin A induces robust ROS production by mitochondria, sufficient to drive NLRP3 inflammasome activation.
“Several studies have shown that inhibition of mitochondrial complex I by rotenone or of complex III by antimycin A induces robust ROS production by mitochondria, which is sufficient to drive NLRP3 inflammasome activation.39, 40”
From Trimethylamine‐N‐Oxide Induces Vascular Inflammation by Activating the NLRP3 Inflammasome Through the SIRT3‐SOD2‐mtROS Signaling Pathway (2017) · cites this paper as [39]
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- Authors
- Huang, L.-S., Cobessi, D., Tung, E. Y., & Berry, E. A.
- Affiliations
- Lawrence Berkeley National Laboratory (US)
- Corresponding author
- Berry, Edward A.
- Venue
- Journal of Molecular Biology
- Publisher
- Elsevier BV
- Published
- 2005-08
- Volume
- 351
- Issue
- 3
- Pages
- 573-597
- ISSN
- 0022-2836 (ISSN-L)
- PMC
- PMC1482829
- OpenAlex
- W2125851804
- Cited by
- 304
- References
- 81
- Citations by year
- 2026: 13 · 2025: 10 · 2024: 13 · 2023: 16 · 2022: 16 · 2021: 16 · 2020: 16 · 2019: 17 · 2018: 12 · 2017: 16 · 2016: 20 · 2015: 18 · 2014: 12 · 2013: 19 · 2012: 15
- FWCI
- 8.74
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Journal of Molecular Biology (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- HAL (submittedVersion)
- eScholarship (California Digital Library) (submittedVersion)
- Funders
- National Institute of General Medical Sciences (R01GM062563, GM62563)
- National Institute of Diabetes and Digestive and Kidney Diseases (DK44842, R01DK044842)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Enzyme Structure and Function
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Mitochondrial Function and Pathology
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Protein Structure and Dynamics
- Keywords
- antimycin A, cytochrome bc1 complex, electron transport inhibition, intramolecular hydrogen bonding, structure-activity relationship, bovine mitochondria, cytochrome b, protein-ligand binding
- MeSH terms
- Animals, Antimycin A, Cattle, Electron Transport, Heme, Mitochondria, Electron Transport Complex III, Ubiquinone, X-Ray Diffraction
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
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