ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Probes for the cocaine receptor. Potentially irreversible ligands for the dopamine transporter

Cite this: J. Med. Chem. 1992, 35, 10, 1813–1817
Publication Date (Print):May 1, 1992
https://doi.org/10.1021/jm00088a017
    ACS Legacy Archive

    Article Views

    193

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    PDF (660 KB)

    Note: In lieu of an abstract, this is the article's first page.

    Free first page

    Cited By

    This article is cited by 48 publications.

    1. Vivek Kumar, Nageswari Yarravarapu, David J. Lapinsky, Danielle Perley, Bruce Felts, Michael J. Tomlinson, Roxanne A. Vaughan, L. Keith Henry, John R. Lever, and Amy Hauck Newman . Novel Azido-Iodo Photoaffinity Ligands for the Human Serotonin Transporter Based on the Selective Serotonin Reuptake Inhibitor (S)-Citalopram. Journal of Medicinal Chemistry 2015, 58 (14) , 5609-5619. https://doi.org/10.1021/acs.jmedchem.5b00682
    2. David J. Lapinsky, Nageswari Yarravarapu, Tammy L. Nolan, Christopher K. Surratt, John R. Lever, Michael Tomlinson, Roxanne A. Vaughan, and Howard M. Deutsch . Evolution of a Compact Photoprobe for the Dopamine Transporter Based on (±)-threo-Methylphenidate. ACS Medicinal Chemistry Letters 2012, 3 (5) , 378-382. https://doi.org/10.1021/ml3000098
    3. Chunyang Jin, Hernán A. Navarro and F. Ivy Carroll. Development of 3-Phenyltropane Analogues with High Affinity for the Dopamine and Serotonin Transporters and Low Affinity for the Norepinephrine Transporter. Journal of Medicinal Chemistry 2008, 51 (24) , 8048-8056. https://doi.org/10.1021/jm801162z
    4. Jianjing Cao,, John R. Lever,, Theresa Kopajtic,, Jonathan L. Katz,, Anh T. Pham,, Muhsinah L. Holmes,, Joseph B. Justice, and, Amy Hauck Newman. Novel Azido and Isothiocyanato Analogues of [3-(4-Phenylalkylpiperazin-1-yl)propyl]bis(4-fluorophenyl)amines as Potential Irreversible Ligands for the Dopamine Transporter. Journal of Medicinal Chemistry 2004, 47 (25) , 6128-6136. https://doi.org/10.1021/jm049670w
    5. F. Ivy Carroll. 2002 Medicinal Chemistry Division Award Address:  Monoamine Transporters and Opioid Receptors. Targets for Addiction Therapy. Journal of Medicinal Chemistry 2003, 46 (10) , 1775-1794. https://doi.org/10.1021/jm030092d
    6. Mu-Fa Zou,, Theresa Kopajtic,, Jonathan L. Katz,, Sara Wirtz,, Joseph B. Justice, Jr., and, Amy Hauck Newman. Novel Tropane-Based Irreversible Ligands for the Dopamine Transporter. Journal of Medicinal Chemistry 2001, 44 (25) , 4453-4461. https://doi.org/10.1021/jm0101904
    7. Satendra Singh. Chemistry, Design, and Structure−Activity Relationship of Cocaine Antagonists. Chemical Reviews 2000, 100 (3) , 925-1024. https://doi.org/10.1021/cr9700538
    8. Aloke K. Dutta,, Cen Xu, and, Maarten E. A. Reith. Tolerance in the Replacement of the Benzhydrylic O Atom in 4-[2-(Diphenylmethoxy)ethyl]-1-benzylpiperidine Derivatives by an N Atom:  Development of New-Generation Potent and Selective N-Analogue Molecules for the Dopamine Transporter. Journal of Medicinal Chemistry 1998, 41 (17) , 3293-3297. https://doi.org/10.1021/jm980066t
    9. Ronghui Lin,, Josep Castells, and, Henry Rapoport. Enantiospecific Synthesis of Natural (−)-Cocaine and Unnatural (+)-Cocaine from d- and l-Glutamic Acid. The Journal of Organic Chemistry 1998, 63 (12) , 4069-4078. https://doi.org/10.1021/jo980153t
    10. Shaili Aggarwal, Ole Valente Mortensen. Discovery and Development of Monoamine Transporter Ligands. 2023, 101-129. https://doi.org/10.1007/978-3-031-21054-9_4
    11. Benjamin G. Chavez, Prashanth Srinivasan, Kayla Glockzin, Neill Kim, Olga Montero Estrada, Jan Jirschitzka, Gage Rowden, Jonathan Shao, Lyndel Meinhardt, Christina D. Smolke, John C. D’Auria. Elucidation of tropane alkaloid biosynthesis in Erythroxylum coca using a microbial pathway discovery platform. Proceedings of the National Academy of Sciences 2022, 119 (49) https://doi.org/10.1073/pnas.2215372119
    12. Neill Kim, Benjamin Chavez, Charles Stewart, John C. D’Auria. Structure and Function of Enzymes Involved in the Biosynthesis of Tropane Alkaloids. 2021, 21-50. https://doi.org/10.1007/978-981-33-4535-5_2
    13. Danielle Krout, Akula Bala Pramod, Rejwi Acharya Dahal, Michael J. Tomlinson, Babita Sharma, James D. Foster, Mu-Fa Zou, Comfort Boatang, Amy Hauck Newman, John R. Lever, Roxanne A. Vaughan, L. Keith Henry. Inhibitor mechanisms in the S1 binding site of the dopamine transporter defined by multi-site molecular tethering of photoactive cocaine analogs. Biochemical Pharmacology 2017, 142 , 204-215. https://doi.org/10.1016/j.bcp.2017.07.015
    14. Neill Kim, Olga Estrada, Benjamin Chavez, Charles Stewart, John D’Auria. Tropane and Granatane Alkaloid Biosynthesis: A Systematic Analysis. Molecules 2016, 21 (11) , 1510. https://doi.org/10.3390/molecules21111510
    15. Gregor Wolfgang Schmidt, Jan Jirschitzka, Tiffany Porta, Michael Reichelt, Katrin Luck, José Carlos Pardo Torre, Franziska Dolke, Emmanuel Varesio, Gérard Hopfgartner, Jonathan Gershenzon, John Charles D’Auria. The Last Step in Cocaine Biosynthesis Is Catalyzed by a BAHD Acyltransferase. Plant Physiology 2015, 167 (1) , 89-101. https://doi.org/10.1104/pp.114.248187
    16. Rejwi Acharya Dahal, Akula Bala Pramod, Babita Sharma, Danielle Krout, James D. Foster, Joo Hwan Cha, Jianjing Cao, Amy Hauck Newman, John R. Lever, Roxanne A. Vaughan, L. Keith Henry. Computational and Biochemical Docking of the Irreversible Cocaine Analog RTI 82 Directly Demonstrates Ligand Positioning in the Dopamine Transporter Central Substrate-binding Site. Journal of Biological Chemistry 2014, 289 (43) , 29712-29727. https://doi.org/10.1074/jbc.M114.571521
    17. David J. Lapinsky, Ranganadh Velagaleti, Nageswari Yarravarapu, Yi Liu, Yurong Huang, Christopher K. Surratt, John R. Lever, James D. Foster, Rejwi Acharya, Roxanne A. Vaughan, Howard M. Deutsch. Azido-iodo-N-benzyl derivatives of threo-methylphenidate (Ritalin, Concerta): Rational design, synthesis, pharmacological evaluation, and dopamine transporter photoaffinity labeling. Bioorganic & Medicinal Chemistry 2011, 19 (1) , 504-512. https://doi.org/10.1016/j.bmc.2010.11.002
    18. Jamshed H. Shah, Gregory E. Agoston, Lita Suwandi, Kimberly Hunsucker, Victor Pribluda, Xiaoguo H. Zhan, Glenn M. Swartz, Theresa M. LaVallee, Anthony M. Treston. Synthesis of 2- and 17-substituted estrone analogs and their antiproliferative structure–activity relationships compared to 2-methoxyestradiol. Bioorganic & Medicinal Chemistry 2009, 17 (20) , 7344-7352. https://doi.org/10.1016/j.bmc.2009.08.038
    19. Chunyang Jin, Hernán A. Navarro, F. Ivy Carroll. Synthesis and structure–activity relationship of 3β-(4-alkylthio, -methylsulfinyl, and -methylsulfonylphenyl)tropane and 3β-(4-alkylthiophenyl)nortropane derivatives for monoamine transporters. Bioorganic & Medicinal Chemistry 2009, 17 (14) , 5126-5132. https://doi.org/10.1016/j.bmc.2009.05.052
    20. David J. Lapinsky, Shaili Aggarwal, Yurong Huang, Christopher K. Surratt, John R. Lever, James D. Foster, Roxanne A. Vaughan. A novel photoaffinity ligand for the dopamine transporter based on pyrovalerone. Bioorganic & Medicinal Chemistry 2009, 17 (11) , 3770-3774. https://doi.org/10.1016/j.bmc.2009.04.057
    21. Berma M Kinsey, David C Jackson, Frank M Orson. Anti‐drug vaccines to treat substance abuse. Immunology & Cell Biology 2009, 87 (4) , 309-314. https://doi.org/10.1038/icb.2009.17
    22. Aleksej Krunić, Dahua Pan, William J. Dunn, S.V. Santhana Mariappan. The stereochemistry of N-methyl and aryl substituents determine the biological activities of 3-aryl-8-methyl-8-azabicyclo[3.2.1]oct-2,3-enes. Bioorganic & Medicinal Chemistry 2009, 17 (2) , 811-819. https://doi.org/10.1016/j.bmc.2008.11.038
    23. Seong-Yeol Nah, Kamal S. Bhatia, Johnnie Lyles, Everett H. Ellinwood, Tong H. Lee. Effects of ginseng saponin on acute cocaine-induced alterations in evoked dopamine release and uptake in rat brain nucleus accumbens. Brain Research 2009, 1248 , 184-190. https://doi.org/10.1016/j.brainres.2008.10.064
    24. James D. Foster, Steven D. Adkins, John R. Lever, Roxanne A. Vaughan. Phorbol ester induced trafficking‐independent regulation and enhanced phosphorylation of the dopamine transporter associated with membrane rafts and cholesterol. Journal of Neurochemistry 2008, 105 (5) , 1683-1699. https://doi.org/10.1111/j.1471-4159.2008.05262.x
    25. M. Laura Parnas, Jon D. Gaffaney, Mu Fa Zou, John R. Lever, Amy Hauck Newman, Roxanne A. Vaughan. Labeling of Dopamine Transporter Transmembrane Domain 1 with the Tropane Ligand N -[4-(4-Azido-3-[ 125 I]iodophenyl)butyl]-2β-carbomethoxy-3β-(4-chlorophenyl)tropane Implicates Proximity of Cocaine and Substrate Active Sites. Molecular Pharmacology 2008, 73 (4) , 1141-1150. https://doi.org/10.1124/mol.107.043679
    26. Vishakantha Murthy, Huw M.L. Davies, Simon J. Hedley, Steven R. Childers. Irreversible binding of a novel phenylisothiocyanate tropane analog to monoamine transporters in rat brain. Biochemical Pharmacology 2007, 74 (2) , 336-344. https://doi.org/10.1016/j.bcp.2007.04.019
    27. Birte Drewes, Wiebke Sihver, Sabine Willbold, Ray A. Olsson, Heinz H. Coenen. New 2α-tropane amides as potential PET ligands for the dopamine transporter. Nuclear Medicine and Biology 2007, 34 (5) , 531-539. https://doi.org/10.1016/j.nucmedbio.2007.04.007
    28. Roxanne A. Vaughan, Dhananjay S. Sakrikar, M. Laura Parnas, Steven Adkins, James D. Foster, Romain A. Duval, John R. Lever, Santosh S. Kulkarni, Amy Hauck-Newman. Localization of Cocaine Analog [125I]RTI 82 Irreversible Binding to Transmembrane Domain 6 of the Dopamine Transporter. Journal of Biological Chemistry 2007, 282 (12) , 8915-8925. https://doi.org/10.1074/jbc.M610633200
    29. M.Rocı́o A. Carrera, Michael M. Meijler, Kim D. Janda. Cocaine pharmacology and current pharmacotherapies for its abuse. Bioorganic & Medicinal Chemistry 2004, 12 (19) , 5019-5030. https://doi.org/10.1016/j.bmc.2004.06.018
    30. Heather L. Kimmel, F. Ivy Carroll, Michael J. Kuhar. Withdrawal from Repeated Cocaine Alters Dopamine Transporter Protein Turnover in the Rat Striatum. Journal of Pharmacology and Experimental Therapeutics 2003, 304 (1) , 15-21. https://doi.org/10.1124/jpet.102.038018
    31. Tong H. Lee, Ramani Balu, Colin Davidson, Everett H. Ellinwood. Differential time‐course profiles of dopamine release and uptake changes induced by three dopamine uptake inhibitors. Synapse 2001, 41 (4) , 301-310. https://doi.org/10.1002/syn.1087
    32. Heather L Kimmel, F.Ivy Carroll, Michael J Kuhar. RTI-76, an irreversible inhibitor of dopamine transporter binding, increases locomotor activity in the rat at high doses. Brain Research 2001, 897 (1-2) , 157-163. https://doi.org/10.1016/S0006-8993(01)02118-7
    33. Willard M Freeman, George J Yohrling, James B Daunais, Lynda Gioia, Stephanie L Hart, Linda J Porrino, Huw M.L Davies, Kent E Vrana. A cocaine analog, 2β-propanoyl-3β-(4-tolyl)-tropane (PTT), reduces tyrosine hydroxylase in the mesolimbic dopamine pathway. Drug and Alcohol Dependence 2000, 61 (1) , 15-21. https://doi.org/10.1016/S0376-8716(00)00119-8
    34. Cory S Freedland, Hilary R Smith, Stephanie L Hart, James B Daunais, Huw M.L Davies, Linda J Porrino. A comparison of the behavioral effects of the repeated administration of PTT, 2β-propanoyl-3β-(4-tolyl)tropane and cocaine. Brain Research 2000, 869 (1-2) , 98-104. https://doi.org/10.1016/S0006-8993(00)02356-8
    35. Heather L Kimmel, F.Ivy Carroll, Michael J Kuhar. Dopamine transporter synthesis and degradation rate in rat striatum and nucleus accumbens using RTI-76. Neuropharmacology 2000, 39 (4) , 578-585. https://doi.org/10.1016/S0028-3908(99)00160-4
    36. David Stout, Andrej Petric, N. Satyamurthy, Quan Nguyen, Sung-Cheng Huang, Mohammad Namavari, Jorge R. Barrio. 2β-carbomethoxy-3β-(4- and 2-[18F]fluoromethylphenyl)tropanes: specific probes for in vivo quantification of central dopamine transporter sites. Nuclear Medicine and Biology 1999, 26 (8) , 897-903. https://doi.org/10.1016/S0969-8051(99)00073-6
    37. Aleksandra Vicentic, George Battaglia, F Ivy Carroll, Michael J Kuhar. Serotonin transporter production and degradation rates: studies with RTI-76. Brain Research 1999, 841 (1-2) , 1-10. https://doi.org/10.1016/S0006-8993(99)01761-8
    38. Jean‐Claude Do Régo, Maria Syringas, Bertrand Leblond, Jean Costentin, Jean‐Jacques Bonnet. Recovery of dopamine neuronal transporter but lack of change of its mRNA in substantia nigra after inactivation by a new irreversible inhibitor characterized in vitro and ex vivo in the rat. British Journal of Pharmacology 1999, 128 (1) , 51-60. https://doi.org/10.1038/sj.bjp.0702784
    39. Roxanne A. Vaughan, Gregory E. Agoston, John R. Lever, Amy Hauck Newman. Differential Binding of Tropane-Based Photoaffinity Ligands on the Dopamine Transporter. The Journal of Neuroscience 1999, 19 (2) , 630-636. https://doi.org/10.1523/JNEUROSCI.19-02-00630.1999
    40. Gregory E. Agoston, Roxanne Vaughan, John R. Lever, Sari Izenwasser, Phyllis D. Terry, Amy Hauck Newman. A novel photoaffinity label for the dopamine transporter based on N-substituted 3α-[bis(4′-fluorophenyl)methoxy]tropane. Bioorganic & Medicinal Chemistry Letters 1997, 7 (23) , 3027-3032. https://doi.org/10.1016/S0960-894X(97)10139-1
    41. James B. Daunais, Stephanie L. Hart, Ashlee Hedgecock-Rowe, Julius J. Matasi, Craig Thornley, Huw M.L. Davies, Linda J. Porrino. Alterations in behavior and opioid gene expression induced by the novel tropane analog WF-31. Molecular Brain Research 1997, 50 (1-2) , 293-304. https://doi.org/10.1016/S0169-328X(97)00203-9
    42. Linda J. Porrino, Mack Miller, Ashlee A. Hedgecock, Craig Thornley, Julius J. Matasi, Huw M.L. Davies. Local cerebral metabolic effects of the novel cocaine analog, WF-31: Comparisons to fluoxetine. Synapse 1997, 27 (1) , 26-35. https://doi.org/10.1002/(SICI)1098-2396(199709)27:1<26::AID-SYN3>3.0.CO;2-F
    43. Yougen Zhan, Amit M. Saindane, Ursula Scheffel, F. Ivy Carroll, Christopher R. Holmquist, John A. Kepler, George F. Taylor, Michael J. Kuhar. RTI-352: A 3? analogue of RTI-55 as an in vivo dopamine transporter binding ligand. Synapse 1997, 25 (4) , 389-392. https://doi.org/10.1002/(SICI)1098-2396(199704)25:4<389::AID-SYN10>3.0.CO;2-Q
    44. Amrat P. Patel, F. Ivy Carroll, Michael J. Kuhar. Turnover of Rat Dopamine Transporter Protein in rDAT-LLC-PK1 Cells. 1997, 231-236. https://doi.org/10.1007/978-3-642-60704-2_17
    45. Susan P. Hume, Sajinder K. Luthra, David J. Brown, Jolanta Opacka-Juffry, Safiye Osman, Sharon Ashworth, Ralph Myers, Frank Brady, F.Ivy Carroll, Michael J. Kuhar, David J. Brooks. Evaluation of [11C]RTI-121 as a selective radioligand for PET studies of the dopamine transporter. Nuclear Medicine and Biology 1996, 23 (3) , 377-384. https://doi.org/10.1016/0969-8051(96)00019-4
    46. John R. Lever, F. Ivy Carroll, Amrat Patel, Philip Abraham, John Boja, Anita Lewin, Robert Lew. Radiosynthesis of a photoaffinity probe for the cocaine receptor of the dopamine transporter: 3β‐( p ‐chlorophenyl)tropan‐2β‐carboxylic acid m ‐([ 125 I]‐iodo)‐ p ‐azidophenethyl ester ([ 125 I]‐RTI‐82). Journal of Labelled Compounds and Radiopharmaceuticals 1993, 33 (12) , 1131-1137. https://doi.org/10.1002/jlcr.2580331207
    47. Ganesh Pandey, G. Lakshmaiah, Anjan Ghatak. Efficient generation and [3+2] cycloaddition of cyclic azomethine ylides: A general synthetic route to x-azabicyclo (m.2.1) alkane framework. Tetrahedron Letters 1993, 34 (45) , 7301-7304. https://doi.org/10.1016/S0040-4039(00)79314-2
    48. Huw M.L. Davies, Elie Saikali, Tammy Sexton, Steven R. Childers. Novel 2-substituted cocaine analogs: binding properties at dopamine transport sites in rat striatum. European Journal of Pharmacology: Molecular Pharmacology 1993, 244 (1) , 93-97. https://doi.org/10.1016/0922-4106(93)90063-F

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect