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2. Synthesis and pharmacological evaluation of pyrazolo[4,3-c]quinolinones as high affinity GABA

Author

Marisa J, López Rivilli, Anahí V, Turina, Elena A, Bignante, Victor H, Molina, María A, Perillo, Margarita C, Briñon, and Elizabeth L, Moyano

Subjects
Male, Behavior, Animal, Dose-Response Relationship, Drug, Molecular Structure, Anxiety, Quinolones, Ligands, Receptors, GABA-A, Rats, Structure-Activity Relationship, Anti-Anxiety Agents, Animals, Rats, Wistar, Maze Learning
Abstract

The synthesis, in vitro ligand binding study and in vivo Elevated Plus Maze test (EPM) of a series of pyrazolo[4,3-c]quinolin-3-ones (PQs) are reported. Multistep synthesis of PQs started from anilines and diethyl 2-(ethoxymethylene)malonate to give the quinolin-4-one nucleus, via the Gould-Jacobs reaction. These quinolinones were transformed to 4-chloroquinolines, which react with aryl-hydrazines affording the final compounds. PQs exhibited different potency in displacing specific [

Published
2018

3. List of Contributors

Author

Renata Rigacci Abdalla, Tomohiro Abekawa, Przemysław Adamczyk, Wendy Adams, Peter H. Addy, Yukio Ago, María Álvaro-Bartolomé, Martina Andellini, Matthew E. Andrzejewski, Gustavo A. Angarita, Mariana Angoa-Pérez, John H. Anneken, Luís Antunes, Yalda Hosseinzadeh Ardakani, Mustafa Aydin, Nima Badri, Ram C. Bajpai, Daniel José Barbosa, Alfonso Barrós-Loscertales, Debasish Basu, Benjamin Becker, Jacob T. Beckley, Pablo García Bermejo, Laís F. Berro, Amanda L. Blaker, Ede Bodoki, Krzysztof Borowiak, Scott E. Bowen, Patricia A. Broderick, Berit Brogaard, Giovana Brolese, T.M. Brunt, T. Buchborn, Eduardo R. Butelman, Raul Caetano, Sónia Campos, Sofija V. Canavan, João Paulo Capela, Manolo Carta, Félix Carvalho, Lucia Carvelli, Briony J. Catlow, Young-Tae Chang, Himanshu K. Chaturvedi, Lela Chilachava, Aree Choodum, Shannon J. Clough, Vanessa Coelho-Santos, Ana Maria Coimbra, Stuart A. Collins, Bru Cormand, Albert Dahan, Elias Dakwar, Antonio Dávalos E., Cor de Jong, Maria de Lourdes Bastos, Marc R. Del Bigio, Teresa Dembińska, Ugur Deveci, D.C. Dieterich, Boukje Dijkstra, Dean E. Dluzen, Margarita L. Dubocovich, Carlos García Esperón, Chun-Kai Fang, Vahid Farnia, Luís Félix, Noelia Fernàndez-Castillo, Daniel Flack, Elisabeth Frauger, Joel Frohlich, Daniela F. Fukushiro, Daniel A. García, M. Julia García-Fuster, Jesús A. García-Sevilla, Eric L. Garland, Dimitria Electra Gatzia, Lia Gelazonia, Abhishek Ghosh, Roy Gigengack, Senobar Golshani, Joana Gonçalves, Javier González-Maeso, Ingmar Gorman, David K. Grandy, G. Grecksch, Alissa M. Greer, Gary A. Gudelsky, Casey Guillot, Joshua M. Gulley, Yoko Hagino, Robert M. Hallock, Emily R. Hankosky, James B. Hanks, Carl Hart, H.W.W. Hasselmann, Hirotake Hida, Sarah E. Hodges, Nicole Holder, André W. Hollais, V. Höllt, Jiri Horacek, Matthew O. Howard, Fleur Margaret Howells, Skye Hsin-Hsien Yeh, Mei Huang, Anthony J. Hutchinson, Jeng-Jong Hwang, Kazutaka Ikeda, Jennifer E. Iudicello, Ahmad Jalloh, Bardia Jamali, Nadezhda Japaridze, Eiichi Jodo, Chantele Joordens, Rasmon Kalayasiri, Rama Kamal, Etsuko Kamegaya, Tadahiro Katayama, Adam W. Keasling, Ruri Kikura-Hanajiri, Matthew Kirkpatrick, Béla Kiss, Rita Kočárová, Saurabh S. Kokane, Mary Jeanne Kreek, Peter R. Kufahl, Donald M. Kuhn, Takeshi Kumazawa, Snezana Kusljic, Krzysztof Łabuz, Maryse Lapeyre-Mestre, Ronaldo Ramos Laranjeira, Andrew J. Lawrence, Byung Dae Lee, Ricardo Alexandre Leitão, L. Stan Leung, Chiang-Shan R. Li, Meng Li, Qing Lin, Felicia Loghin, Elena López-Cancio M., Jennifer Lyke, Michael Lyvers, Scott Macdonald, Clarice Sandi Madruga, Michael Maes, Timothy J. Maher, Jingyi Ma, Chitra D. Mandyam, Claudia Mardones, Gina Martin, Luciana Massaro, Toshio Matsuda, M.T.B. McMaster, Richard H. Melloni, Herbert Y. Meltzer, Joëlle Micallef, Maria Mironidou-Tzouveleki, Masayoshi Mishina, Sandro Mitsuhiro, Christian Montag, Elisabeth Moore, Erin E. Morgan, Peter T. Morgan, Satoshi Morimoto, Thomas R. Morrison, Anna Moszczynska, Akihiro Mouri, Antonio Napolitano, Nichole M. Neugebauer, Niamh NicDaeid, Charles D. Nichols, Martin Nizama-Valladolid, Yukihiro Noda, Nicole A. Northrop, M. Foster Olive, Rory D. Ostrow, Linda C.J. Oudejans, Tomas Palenicek, Arvind Pandey, Mariusz Papp, Ioannis D. Passos, Madan Kumar Paudel, Maria A. Perillo, Christina J. Perry, Nataša Petronijević, Siripan Phattanarudee, Ilana Pinsky, Nino Pochkhidze, Anca Pop, Marianne Possa, Barbara Potocka-Banaś, Boris B. Quednow, Nevena V. Radonjić, Lakshmi Rajagopal, Marta Ribasés, Lesley A. Ricci, Carola Vergara Rosales, Mohammad-Reza Rouini, Juan Sanchez-Ramos, Renan Santos-Baldaia, Siddharth Sarkar, Kaori Sasaki-Tabata, Naomi Sato, Tomonori Sato, Wakako Sawada, Silvia Bassani Schuch, Setsuko Sekita, Eduardo Alvear Serrano, Behjat Sheikholeslami, Osamu Shirota, Ana Paula Silva, Nicola Simola, Derek P. Simon, Ichiro Sora, Anne Orgler Sordi, Mitchell G. Spring, Katarzyna Stebelska, Haruhiko Sugimura, Yoshiaki Suzuki, Kazuhiro Takuma, Hiroyuki Tanaka, Meshkat Torkamanian, Pasarapa Towiwat, Anahí V. Turina, Filip Tyls, J.G.C. van Amsterdam, W. van den Brink, Maarten van den Buuse, John Darrell Van Horn, Martijn van Noorden, Monique van Velzen, Carlos Venâncio, Dietrich von Baer, Lisia von Diemen, Martin Walter, Fang Wang, Erica Weber, Petr Winkler, Steven Paul Woods, John J. Woodward, Chun-Fu Wu, Raphael Wuo-Silva, Wang Xu, Bryan K. Yamamoto, Hideko Yamamoto, Toshifumi Yamamoto, Jing-Yu Yang, Duanting Zhai, Mzia Zhvania, and Jordan K. Zjawiony

Published
2016

4. Monoterpenes affect chlorodiazepoxide–micelle interaction through micellar dipole potential modifications

Author

Anahí V, Turina, Anahí V, del Turina, and María A, Perillo

Subjects
BENZODIAZEPINE, TRITON X-100, Octoxynol, Stereochemistry, Monoterpene, Otras Ciencias Biológicas, Static Electricity, ACID-BASE EQUILIBRIUM, Biophysics, DIELECTRIC CONSTANT, Pyrimidinones, CDX, Photochemistry, Micelle, Biochemistry, Acid–base equilibrium, Ciencias Biológicas, chemistry.chemical_compound, GABA, CHLORODIAZEPOXIDE, MEROCYANINE, Phase (matter), Merocyanine, DIPOLAR POTENTIAL, GAMMA-AMINOBUTYRIC ACID, Micelles, Acid-Base Equilibrium, Triton X-100, Dipolar potential, BZD, Chlordiazepoxide, Cell Biology, Dipole, Membrane, Monomer, MONOTERPENE, chemistry, GABA RECEPTOR, Chlorodiazepoxide, Monoterpenes, GABAA-R, CIENCIAS NATURALES Y EXACTAS
Abstract

The ability of several natural terpenes to affect benzodiazepine (BZD)-micelle interaction through the membrane dipolar organization was investigated. The acid-base equilibrium of chlorodiazepoxide (CDX) and the spectroscopic behavior of the electrochromic dye merocyanine were tested in the presence and in the absence of Triton X-100 micelles (used to mimic a membrane environment) containing or not cineole, menthol, geraniol or camphor. CDX's apparent pK increased in the environment of terpene-containing micelles compared with pure Triton X-100 micelles. Decrements in electric potentials (between -111 and -128 mV with respect to pure detergent) were calculated from Boltzmann equation. This result suggested, that in the presence of terpenes, the tendency of CDXH+ to remain in the membrane phase increased. The dielectric constant (D) of the microenvironment sensed by merocyanine within Triton X-100 micelles, determined from λmax,2 of merocyanine monomer, was D=9 and increased in the presence of all the terpenes assayed (D≅11). The decrease in merocyanine partitioning (Apeak1/A peak2 increased) also reflected an increment in the negative dipole potential. The present results suggest that terpenes contributed to the whole dipolar arrangement of the micelle with a dipole moment vector which had an intense component oriented parallel to the intrinsic dipole of the Triton X-100 molecules in the micelles. This led to a more negative environment of the interface region where CDX was located, and increased the net polarity of the deepest micelle regions sensed by merocyanine. © 2003 Elsevier B.V. All rights reserved. Fil: Turina, Anahi del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones Biológicas y Tecnológicas. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Instituto de Investigaciones Biológicas y Tecnológicas; Argentina Fil: Perillo, Maria Angelica. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones Biológicas y Tecnológicas. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Instituto de Investigaciones Biológicas y Tecnológicas; Argentina

Published
2003
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