Cation−π Interactions in Ligand Recognition by Serotonergic (5-HT3A) and Nicotinic Acetylcholine Receptors: The Anomalous Binding Properties of Nicotine

Beene, Darren L., Brandt, Gabriel S., Zhong, Wenge, Zacharias, Niki M., Lester, Henry A., Dougherty, Dennis A.·2002·Biochemistry

Cited by (316)

Items 201–300 of 316

  1. Medicinal Chemistry of α4β2 Nicotinic Cholinergic Receptor Ligands
    Richard A. Glennon · 2004 · Progress in medicinal chemistry
  2. Investigating the function and possible biological role of an acetylcholine-gated chloride channel subunit (ACC-1) from the parasitic nematode Haemonchus contortus
    Micah K. Callanan, Sarah A. Habibi, Wen Jing Law, Kristen Nazareth, Richard L. Komuniecki, Sean G. Forrester · 2018 · International Journal for Parasitology Drugs and Drug Resistance
  3. Molecular Recognition of Rhodopsin Kinase GRK1 and Recoverin Is Tuned by Switching Intra- and Intermolecular Electrostatic Interactions
    Seher Abbas, Valerio Marino, Daniele Dell’Orco, Karl‐Wilhelm Koch · 2019 · Biochemistry
  4. Specificity of Loxosceles α clade phospholipase D enzymes for choline-containing lipids: Role of a conserved aromatic cage
    Emmanuel E. Moutoussamy, Qaiser Waheed, Greta J. Binford, Hanif Muhammad Khan, Shane M. Moran, Anna R. Eitel, Matthew H. J. Cordes, Nathalie Reuter · 2022 · PLoS Computational Biology
  5. The Startle Disease Mutation E103K Impairs Activation of Human Homomeric α1 Glycine Receptors by Disrupting an Intersubunit Salt Bridge across the Agonist Binding Site
    Fatemah Safar, Elliot Hurdiss, Marios Erotocritou, Timo Greiner, Remigijus Lapė, Mark William Irvine, Guangyu Fang, David E. Jane, Rilei Yu, Marc A. Dämgen et al. · 2017 · Journal of Biological Chemistry
  6. Cation–π interactions in gaseous ω-phenylalkyloxonium ions
    Barbara Chiavarino, Maria Elisa Crestoni, Simonetta Fornarini · 2004 · International Journal of Mass Spectrometry
  7. The state of ion channel research in 2004
    The Nature Reviews Drug Discovery Ion Channel Questionnaire Participants · 2004 · Nature Reviews Drug Discovery
  8. Dynamics of Noncovalent Interactions in All-α and All-β Class Proteins: Implications for the Stability of Amyloid Aggregates
    Alok K. Jain, Ramasubbu Sankararamakrishnan · 2011 · Journal of Chemical Information and Modeling
  9. Modelling of interactions between volatile anaesthetics (halothane, enflurane) and aromatic compounds, ab initio study
    Wiktor Zierkiewicz · 2010 · Chemical Physics
  10. Carbamoylcholine homologs: synthesis and pharmacology at nicotinic acetylcholine receptors
    Anders A. Jensen, Ivan Mikkelsen, Bente Frølund, Karla Frydenvang, Lotte Brehm, Jerzy W. Jaroszewski, Hans Bräuner‐Osborne, Erik Falch, Povl Krogsgaard‐Larsen · 2004 · European Journal of Pharmacology
  11. Development of 99mTc radiolabeled A85380 derivatives targeting cerebral nicotinic acetylcholine receptor: Novel radiopharmaceutical ligand 99mTc-A-YN-IDA-C4
    Daisuke Mori, Hiroyuki Kimura, Hidekazu Kawashima, Yusuke Yagi, Kenji Arimitsu, Masahiro Ono, Hideo Saji · 2019 · Bioorganic & Medicinal Chemistry
  12. Functionalized olympicene (C19H12) as anode material for Li-ion batteries: a DFT approach
    Ehsan Shakerzadeh · 2019 · Monatshefte für Chemie - Chemical Monthly
  13. A Hydrosoluble Triphenylene That Preferentially Binds Acetylcholine, Epibatidine, and Nicotine
    Cécile Givelet, Thierry Buffeteau, Françoise Arnaud‐Neu, Véronique Hubscher‐Bruder, Brigitte Bibal · 2009 · The Journal of Organic Chemistry
  14. Protonated serotonin: Geometry, electronic structures and photophysical properties
    Reza Omidyan, Zohreh Amanollahi, Gholamhassan Azimi · 2017 · Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy
  15. The nematode serotonin-gated chloride channel MOD-1: A novel target for anthelmintic therapy
    Noelia Rodriguez Araujo, Guillermina Hernando, Jeremías Corradi, Cecilia Bouzat · 2022 · Journal of Biological Chemistry
  16. Charge-charge and cation-π interactions in ligand binding to G protein-coupled receptors
    Nicole Dölker, Xavier Deupí, Leonardo Pardo, Mercedes Campillo · 2007 · Theoretical Chemistry Accounts
  17. Heterologous expression and nonsense suppression provide insights into agonist behavior at α6β2 nicotinic acetylcholine receptors
    Michael R. Post, Walrati Limapichat, Henry A. Lester, Dennis A. Dougherty · 2015 · Neuropharmacology
  18. ‘Biting effect’ stabilizing gallate-type catechin/quaternary ammonium ion complexes
    Nobuyuki Hayashi, Tomomi Ujihara · 2007 · Tetrahedron
  19. Crotonic Acid Blocks the Gloeobacter Ligand-Gated Ion Channel (GLIC) via the Extracellular Domain
    Mona Alqazzaz, Kerry L. Price, Sarah C. R. Lummis · 2016 · Biochemistry
  20. A comprehensive study on the 5-hydroxytryptamine3A receptor binding of agonists serotonin and m-chlorophenylbiguanidine
    Eszter Hazai, Prasad Joshi, Edward C. Skoviak, Asha Suryanarayanan, Marvin K. Schulte, Zsolt Bikádi · 2009 · Bioorganic & Medicinal Chemistry
  21. Use of Calculated Cation-π Binding Energies to Predict Relative Strengths of Nicotinic Acetylcholine Receptor Agonists
    Mathew Tantama, Stuart Licht · 2008 · ACS Chemical Biology
  22. Study of the Interaction of Chlorisondamine and Chlorisondamine Analogues with an Epitope of the α-2 Neuronal Acetylcholine Nicotinic Receptor Subunit
    Hay‐Yan J. Wang, Andrew E. Taggi, Jerrold Meinwald, Roy A. Wise, Amina S. Woods · 2005 · Journal of Proteome Research
  23. Conformational dynamics of a nicotinic receptor neurotransmitter site
    Mrityunjay Singh, Dinesh C. Indurthi, Lovika Mittal, Anthony L. Auerbach, Shailendra Asthana · 2024 · eLife
  24. Synthesis of α3β4 Nicotinic Acetylcholine Receptor Modulators Derived from Aristoquinoline That Reduce Reinstatement of Cocaine-Seeking Behavior
    Lisa E. Rusali, Ana M. Lopez-Hernandez, Kyle M. Kremiller, Gauri Kulkarni, Abhishek Gour, Carolyn J. Straub, Malaika D. Argade, Christian J. Peters, Abhisheak Sharma, Lawrence Toll et al. · 2023 · Journal of Medicinal Chemistry
  25. Progress in the Understanding of Traditional and Nontraditional Molecular Interactions
    Robin Taylor · 2016 · Elsevier eBooks
  26. Multiple regions in the extracellular domain of the glycine receptor determine receptor activity
    Bijun Tang, Sarah C. R. Lummis · 2018 · Journal of Biological Chemistry
  27. Mapping the Orthosteric Binding Site of the Human 5-HT3 Receptor Using Photo-cross-linking Antagonists
    Thomas Jack, Michele Leuenberger, Marc‐David Ruepp, Sanjeev Kumar V. Vernekar, Andrew J. Thompson, Sophie Braga-Lagache, Manfred Heller, Martin Lochner · 2018 · ACS Chemical Neuroscience
  28. Conformational properties of chiral tobacco alkaloids by DFT calculations and vibrational circular dichroism: (−)-S-anabasine
    Pilar Gema Rodríguez Ortega, Manuel Montejo, F. Márquez, Juan Jesús López González · 2015 · Journal of Molecular Graphics and Modelling
  29. Small molecules and chemical tools at the interface
    Robert Howard Newman, Jin Zhang · 2008 · Nature Chemical Biology
  30. Modular incorporation of 1-benzyltryptophan into dipeptide hosts that bind acetylcholine in pure water
    Cory S. Beshara, Fraser A. Hof · 2010 · Canadian Journal of Chemistry
  31. Activation and Desensitization of Peripheral Muscle and Neuronal Nicotinic Acetylcholine Receptors by Selected, Naturally-Occurring Pyridine Alkaloids
    Benedict Green, Stephen Lee, Kevin D. Welch, Daniel Cook, William R. Kem · 2016 · Toxins
  32. DFT and TDDFT study on cation-π complexes of diboryne (NHC → B ≡ B←NHC)
    Kusum Kumar Bania, Ankur Kanti Guha, P. Bhattacharyya · 2016 · The Journal of Chemical Physics
  33. Subunit rotation models activation of serotonin 5-HT3AB receptors by agonists
    G. Maksay, Mikl�s Simonyi, Zsolt Bik�di · 2004 · Journal of Computer-Aided Molecular Design
  34. Genetic Code Expansion for Mechanistic Studies in Ion Channels: An (Un)natural Union of Chemistry and Biology
    Daniel T. Infield, Miranda E. Schene, Jason D. Galpin, Christopher A. Ahern · 2024 · Chemical Reviews
  35. Anion–π interactions in adducts of anionic guests with octahydroxy-pyridine[4]arene: theoretical and experimental elucidation
    Alexander B. Rozhenko, Wolfgang W. Schoeller, Matthias C. Letzel, Björn Decker, Jochen Mattay · 2012 · New Journal of Chemistry
  36. Structure–Activity Studies of Diazabicyclo[3.3.0]octane-Substituted Pyrazines and Pyridines as Potent α4β2 Nicotinic Acetylcholine Receptor Ligands
    Marc J. C. Scanio, Lei Shi, William H. Bunnelle, David J. Anderson, Rosalind J. Helfrich, John Malysz, Kirsten Thorin‐Hagene, Ceclia E. Van Handel, Kennan C. Marsh, Chih‐Hung Lee et al. · 2011 · Journal of Medicinal Chemistry
  37. The extracellular subunit interface of the 5-HT3receptors: a computational alanine scanning mutagenesis study
    Francesca De Rienzo, Arménio Jorge Moura Barbosa, Marta A. S. Perez, Pedro Alexandrino Fernandes, Maria João Ramos, Maria Cristina Menziani · 2012 · Journal of Biomolecular Structure and Dynamics
  38. Importance of recognition loops B and D in the activation of human 5-HT3 receptors by 5-HT and meta-chlorophenylbiguanide
    Sheldon D. Michaelson, Isabelle M. Paulsen, Janna L. Kozuska, Ian L. Martin, Susan M. J. Dunn · 2013 · Neuropharmacology
  39. Influence of arene–arene interactions on the conformation of acyclic molecules:1H NMR and dipole moment experimental results
    Pablo Bello, Nicholas J. Heaton, Antonio Chana, Jesús Jiménez‐Barbero, Evaristo Riande, Bernardo Herradón · 2003 · Journal of Physical Organic Chemistry
  40. Downregulation of eRF1 by RNA interference increases mis-acylated tRNA suppression efficiency in human cells
    Erwin Ilegems, Horst Matthias Pick, Horst Vogel · 2004 · Protein Engineering Design and Selection
  41. Infrared Spectroscopy of Protonated Trimethylamine–(Benzene)n (n = 1–4) as Model Clusters of the Quaternary Ammonium–Aromatic Ring Interaction
    Ryunosuke Shishido, Yuki Kawai, Asuka Fujii · 2014 · The Journal of Physical Chemistry A
  42. Investigations of Ion Channel Structure-Function Relationships Using Molecular Modeling and Experimental Biochemistry
    Donald E. Elmore · 2004 · CaltechTHESIS (California Institute of Technology)
  43. Cocaine chemogenetics blunts drug-seeking by synthetic physiology
    Juan L. Gomez, Christopher J. Magnus, Jordi Bonaventura, Óscar Solís, Fallon P. Curry, Marjorie R. Levinstein, Reece C. Budinich, Meghan L. Carlton, Emilya N. Ventriglia, Sherry Lam et al. · 2025 · Nature
  44. Ortho‐7 bound to the active‐site gorge of free and OP ‐conjugated acetylcholinesterase: Cation–π interactions
    Arup Kumar Pathak, Tusar Bandyopadhyay · 2015 · Biopolymers
  45. Isolation and characterization of a novel member of the ACC ligand-gated chloride channel family, Hco-LCG-46, from the parasitic nematode Haemonchus contortus
    Sarah A. Habibi, Stephen M. Blazie, Yishi Jin, Sean G. Forrester · 2020 · Molecular and Biochemical Parasitology
  46. A REVIEW ON SUPRAMOLECULAR CHEMISTRY IN DRUG DESIGN AND FORMULATION RESEARCH
    Suresh Babu Vepuri, S. Anbazhagan, Dhanaraj Divya, D. Sai Padmini · 2013 · DOAJ (DOAJ: Directory of Open Access Journals)
  47. Investigations of 3-Hydroxy Chromone Derivatives as Multipotent Therapeutics for the Treatment of Alzheimer’s Disease: In Silico and In Vitro Interventions and Fluorescence Studies
    Naveen Kumar, Kailash Jangid, Vinay Kumar, Bharti Devi, Tania Arora, Jayapriya Mishra, Vijay Kumar, Ashish Ranjan Dwivedi, Jyoti Parkash, Jasvinder Singh Bhatti et al. · 2025 · ACS Chemical Neuroscience
  48. Non-covalent interactions drive the self-assembly to enhanced stability of peptide-based nanomaterials
    Yakun Ding, Sinuo Yang, Jie Chen, Mengran Xing, Dongxin Ma, Junhao Wang, Shuaifeng Gu, Muhammad Ali Khan, Haihong Hao · 2026 · Chemical Engineering Journal
  49. Small-Molecule Modulation of Methyl-Lysine-Mediated Interactions
    Stephen V. Frye, Lindsey Ingerman James · 2015 · Springer eBooks
  50. Unfolding of Tryptophanoctyl Ester and Elastic Deformation of Host Micelles via RR'3N+⋅⋅⋅π Interaction: Conceivable Relevance to Wrapping Process of Receptor Mediated Endocytosis
    Gulmi Chakraborty, Soumik Bardhan, Swapan Kumar Saha · 2021 · ChemPhysChem
  51. Affinity of ferrocene and (1,1′)(3,3′)[3,3]ferrocenophane to cations
    Antonio Frontera, David Quiñonero, Carolina Garau, Pere M. Deyà, Fabio Pichierri · 2006 · Chemical Physics Letters
  52. Cation–π Interactions
    Yi An, Steven E. Wheeler · 2015 · Encyclopedia of Inorganic and Bioinorganic Chemistry
  53. Revealing a notable interaction in the binding of type II statins to HMG‐CoA reductase: Stacked cation– π interaction
    Aliakbar Ahmadi, Mojgan Ayoubi‐Chianeh, M.Z. Kassaee, Alireza Fattahi · 2023 · Journal of Physical Organic Chemistry
  54. In Vivo Studies of Receptors and Ion Channels with Unnatural Amino Acids
    Dennis A. Dougherty · 2009 · Nucleic acids and molecular biology
  55. Phosphatidylcholine with C26:0 moiety, a precursor of a diagnostic marker for X-ALD, is synthesized by LPLAT10/LPEAT2
    Kotaro Hama, Yuko Fujiwara, Koko Imai, Yoshio Kusakabe, Yasuhiro Hayashi, Shigeo Takashima, Shohei Azuma, Masaru Kondo, Atsushi Yamashita, Ryo Takita et al. · 2025 · Journal of Lipid Research
  56. Interplay of Noncovalent Interactions in Phase Separation Mediated by Tyrosine-Rich and Arginine-Rich Polypeptides
    Ruiwen Xu, Rui Wang, Cindy Qiu, Jiani Niu, Desiree M. Bates, Nicholas Lawrence Abbott, Samuel H. Gellman · 2026 · Journal of the American Chemical Society
  57. Genetic code expansion, an emerging tool in the Ca2+ ion channel field
    Julia Söllner, Isabella Derler · 2024 · The Journal of Physiology
  58. Molecular Structure, Gating, and Regulation
    Steen E. Pedersen · 2014 · The Receptors
  59. Protein Engineering Using Noncanonical Amino Acids
    Deniz Yüksel, Yulia Ivanova, Diren Pamuk, Krishna Kumar · 2009 · CRC Press eBooks
  60. Toxic plants
    Kevin D. Welch, Benedict T. Green, Dale R. Gardner, Clinton A. Stonecipher, Daniel Cook · 2022 · Elsevier eBooks
  61. Electron Transfers and Holographic Molecules: Why Neuroscientists Should Take Quantum Phenomena into Consideration
    Philippe Anglade, Yamina Larabi, Shigeru Tsuji · 2014 · NeuroQuantology
  62. STRUCTURE ACTIVITY RELATIONSHIPS OF NICOTINE ANALOGS AND Erythrina ALKALOIDS ON THE ALPHA 4 BETA 2 NICOTINIC ACETYLCHOLINE RECEPTOR
    Kristin M. Wildeboer · 2005
  63. 5-HT3 Receptors
    Li Zhang, Sarah C. R. Lummis · 2006 · Informa Healthcare eBooks
  64. Conformational dynamics of a nicotinic receptor neurotransmitter binding site
    Mrityunjay Singh, Dinesh C. Indurthi, Lovika Mittal, Anthony L. Auerbach, Shailendra Asthana · 2024 · eLife
  65. Expression and purification of fluorinated proteins from mammalian suspension culture
    Miranda E. Schene, Daniel T. Infield, Christopher A. Ahern · 2024 · Methods in enzymology on CD-ROM/Methods in enzymology
  66. Chemical tuning reveals a cation–π gating bridge between the voltage-sensor and pore domains in the K v 7.1 potassium channel
    Miranda E. Schene, Christopher A. Ahern · 2026 · Proceedings of the National Academy of Sciences
  67. An Improved Commercial Method for Determination of Nicotine in Tobacco
    Md. Wasim Aktar, M. Paramasivam, Dwaipayan Sengupta · 2010 · Journal of Herbs Spices & Medicinal Plants
  68. First-principles study on MRh12 (M = Rh, Fe, Co, AND Ni) clusters
    Xiang Jun Kuang, Xiang Wang, Gang Liu · 2011 · Journal of Structural Chemistry
  69. Effects of 5-hydroxytryptamine on Rocuronium-induced Neuromuscular Blockade in a Rat Phrenic Nerve-hemidiaphragm Preparation
    Woo-Jong Choi, Hye Jin Kim, Yoon Kyung Lee, Hong Seuk Yang · 2007 · Korean Journal of Anesthesiology
  70. Computational studies of biologically active alkaloids of plant origin: an overview
    Mireille Kabuyi Bilonda, Лилиана Маммино · 2020 · Physical Sciences Reviews
  71. Structure-Function Studies of Nicotinic Acetylcholine Receptors Using Unnatural Amino Acids
    Nyssa L. Puskar · 2012 · CaltechTHESIS (California Institute of Technology)
  72. Cation–π interactions modulate the NMDA receptor inhibitory potencies of inhaled aromatic anesthetics
    Douglas E. Raines · 2005 · International Congress Series
  73. The role of biotransformation in the estrogenicity of xenobiotics
    Jelle Reinen · 2010 · Digital Academic REpository of VU University Amsterdam (Vrije Universiteit Amsterdam)
  74. A Chemical-Scale Study on the Ligand-Binding Site of a Serotonin-Gated Ion Channel
    Ting‐Wei Mu · 2006
  75. Interaction of a G protein-coupled receptor (Ste2p) of Saccharomyces cerevisiae with its ligand and its G-protein alpha subunit
    Li-Yin Huang · 2011
  76. Mutational-kinetic Analysis Reveals the Roles of Arginines and Aromatics in the Core of the GABAA Receptor Ligand-binding Pocket
    Phu N. Tran · 2011 · e-Publications@Marquette (Marquette University)
  77. Single-Molecule Studies of Ion Channels Expressing Unnatural Amino Acids
    Jai A. P. Shanata · 2011 · CaltechTHESIS (California Institute of Technology)
  78. Ligand Binding Studies in R67 Dihydrofolate Reductase and the Evaluation of the Anion-Quadrupole Interaction at a Quantum Mechanical Level
    Michael R. Jackson · 2005
  79. A theoretical study of the interaction between [HB≡CH]−, [H2B=CH2]−, and boratabenzene anions with alkali and alkaline earth metals: properties and structures
    Reza Ghiasi, Ali Moghimi · 2011 · Journal of Structural Chemistry
  80. In vivo protein labeling for structural and functional investigation of the 5-HT3A neurotransmitter receptor
    Erwin Ilegems · 2004 · reroDoc Digital Library
  81. Applications of Computational Protein Design
    Jessica Mao · 2006 · CaltechTHESIS (California Institute of Technology)
  82. Effects of Ondansetron and Granisetron on Rocuronium-induced Neuromuscular Blockade in a Rat Phrenic Nerve-hemidiaphragm Preparation
    Chong Wha Baek, Hyun Kang, Yong Hun Jung, Jung‐Won Park, Hwa Sung Jung, Yoon Kyung Lee, Hong Seuk Yang · 2006 · Korean Journal of Anesthesiology
  83. MECHANISMS OF GATING AND MODULATION IN THE FAMILY OF CYS-LOOP RECEPTORS
    Nicolaus Schmandt · 2016 · OhioLink ETD Center (Ohio Library and Information Network)
  84. A CATION- INTERACTION AT A PHENYLALANINE RESIDUE IN THE
    Stephan Alexander Pless, Ariele P. Hanek, Joseph W. Lynch, Alistair J. Henry, Dennis A. Dougherty, Sarah C. R. Lummis · 2011
  85. TOWARDS AN UNDERSTANDING OF PHARMACOLOGICALLY INDUCED INTRACELLULAR CHANGES IN NICOTINIC ACETYLCHOLINE RECEPTORS
    Ashley M. Fox-Loe · 2016 · UKnowledge (University of Kentucky)
  86. Chemical scale investigations of ligand-gated ion channels using unnatural amino acids
    Darren L. Beene · 2005 · CaltechTHESIS (California Institute of Technology)
  87. Comparison of Cation-π and Anion-π Interactions by Way of Antiaromaticity
    Pouya Karimi · 2018 · Russian Journal of Physical Chemistry A
  88. Isolation and partial characterization of three members of the GGR-1 family in the parasitic nematode Haemonchus contortus
    Kristen Nazareth · 2019 · e-scholar@UOIT (University of Ontario Institute of Technology)
  89. Exploring the Structures and Properties of Cationic Aromatic Clusters
    Weiqiang Fu · 2020 · UWSpace (University of Waterloo)
  90. Conclusions and Future Directions
    Kieran L. Hudson · 2018 · Springer theses
  91. Cation–π Interactions
    Dennis A. Dougherty · 2004 · CRC Press eBooks
  92. Conformational dynamics of a nicotinic receptor neurotransmitter site
    Mrityunjay Singh, Dinesh C. Indurthi, Lovika Mittal, Anthony L. Auerbach, Shailendra Asthana · 2024 · eLife
  93. Reviewer #4 (Public Review): Conformational dynamics of a nicotinic receptor neurotransmitter binding site
    2024 · eLife
  94. Conformational dynamics of a nicotinic receptor neurotransmitter binding site
    Mrityunjay Singh, Dinesh C. Indurthi, Lovika Mittal, Anthony L. Auerbach, Shailendra Asthana · 2024 · eLife
  95. Reviewer #3 (Public Review): Conformational dynamics of a nicotinic receptor neurotransmitter binding site
    2024 · eLife
  96. Conformational dynamics of a nicotinic receptor neurotransmitter site
    Mrityunjay Singh, Dinesh C. Indurthi, Lovika Mittal, Anthony L. Auerbach, Shailendra Asthana · 2024 · eLife
  97. Reviewer #4 (Public Review): Conformational dynamics of a nicotinic receptor neurotransmitter site
    2024 · eLife
  98. eLife Assessment: Conformational dynamics of a nicotinic receptor neurotransmitter site
    Marcel P Goldschen-Ohm · 2024 · eLife
  99. Reviewer #2 (Public Review): Conformational dynamics of a nicotinic receptor neurotransmitter site
    2024 · eLife
  100. Progress in the understanding of traditional and nontraditional molecular interactions
    Robin Taylor, Jason C. Cole · 2025 · Elsevier eBooks