ArticleThe Journal of biological chemistry2011
Derivatives of rhodamine 19 as mild mitochondria-targeted cationic uncouplers.
Article in The Journal of biological chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed, 94 citations in OpenAlex.
- Nanoparticle Drug Delivery Systems: The Future Direction for the Treatment of Tumors.International journal of nanomedicine · 2026Review
- The impact of mitochondrial dysfunction on osteoarthritis cartilage: current insights and emerging mitochondria-targeted therapies.Bone research · 2025Review
- Modification in Structures of Active Compounds in Anticancer Mitochondria-Targeted Therapy.International journal of molecular sciences · 2025Review
- MicroRNAs regulating apoptosis and delivery strategies for treating intervertebral disc degeneration.Frontiers in cell and developmental biology · 2025Review
- Rhodamine 19 Alkyl Esters as Effective Antibacterial Agents.International journal of molecular sciences · 2024Article
- Late-Stage Functionalization of Living Organisms: Rethinking Selectivity in Biology.Chemical reviews · 2024Review
- Mitochondrial ATP Synthase and Mild Uncoupling by Butyl Ester of Rhodamine 19, C4R1.Antioxidants (Basel, Switzerland) · 2023Article
- Mitochondrial heteroplasmy as a cause of cell-to-cell phenotypic heterogeneity in clonal populations.Frontiers in cell and developmental biology · 2023Article
- Mitochondrial Dysfunction: Pathophysiology and Mitochondria-Targeted Drug Delivery Approaches.Pharmaceutics · 2022Review
- Prescription drugs and mitochondrial metabolism.Bioscience reports · 2022Review
- Novel Strategies for Disrupting Cancer-Cell Functions with Mitochondria-Targeted Antitumor Drug-Loaded Nanoformulations.International journal of nanomedicine · 2021Review
- Recent Advances in Chemical Biology of Mitochondria Targeting.Frontiers in chemistry · 2021Review
- Mitocans Revisited: Mitochondrial Targeting as Efficient Anti-Cancer Therapy.International journal of molecular sciences · 2020Review
- Lipophilic Cations Rescue the Growth of Yeast under the Conditions of Glycolysis Overflow.Biomolecules · 2020Article
- Article
- Mitochondria-targeted triphenylphosphonium-based compounds do not affect estrogen receptor α.PeerJ · 2020Article
- Discovery of a new mitochondria permeability transition pore (mPTP) inhibitor based on gallic acid.Journal of enzyme inhibition and medicinal chemistry · 2018Article
- Mitochondria-targeting drug conjugates for cytotoxic, anti-oxidizing and sensing purposes: current strategies and future perspectives.Acta pharmaceutica Sinica. B · 2018Review
- Effect of Alkyl Chain Length on Translocation of Rhodamine B n-Alkyl Esters across Lipid Membranes.Biophysical journal · 2018Article
- Ionophoric effects of the antitubercular drug bedaquiline.Proceedings of the National Academy of Sciences of the United States of America · 2018Article
Corrections and comments
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Authors and funding
17 authors at 4 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A limited decrease in mitochondrial membrane potential can be beneficial for cells, especially under some pathological conditions, suggesting that mild uncouplers (protonophores) causing such an effect are promising candidates for therapeutic uses. The great majority of protonophores are weak acids capable of permeating across membranes in their neutral and anionic forms. In the present study, protonophorous activity of a series of derivatives of cationic rhodamine 19, including dodecylrhodamine (C(12)R1) and its conjugate with plastoquinone (SkQR1), was revealed using a variety of assays. Derivatives of rhodamine B, lacking dissociable protons, showed no protonophorous properties. In planar bilayer lipid membranes, separating two compartments differing in pH, diffusion potential of H(+) ions was generated in the presence of C(12)R1 and SkQR1. These compounds induced pH equilibration in liposomes loaded with the pH probe pyranine. C(12)R1 and SkQR1 partially stimulated respiration of rat liver mitochondria in State 4 and decreased their membrane potential. Also, C(12)R1 partially stimulated respiration of yeast cells but, unlike the anionic protonophore FCCP, did not suppress their growth. Loss of function of mitochondrial DNA in yeast (grande-petite transformation) is known to cause a major decrease in the mitochondrial membrane potential. We found that petite yeast cells are relatively more sensitive to the anionic uncouplers than to C(12)R1 compared with grande cells. Together, our data suggest that rhodamine 19-based cationic protonophores are self-limiting; their uncoupling activity is maximal at high membrane potential, but the activity decreases membrane potentials, which causes partial efflux of the uncouplers from mitochondria and, hence, prevents further membrane potential decrease.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.