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

Lipophilic cations: a group of model substrates for the multidrug-resistance transporter

Cite this: Biochemistry 1992, 31, 7, 1992–1998
Publication Date (Print):February 1, 1992
    ACS Legacy Archive

    Article Views





    Other access options

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

    Free first page

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.


    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Cited By

    This article is cited by 63 publications.

    1. Oliver J. Klein, Brijesh Bhayana, Yong Jin Park, and Conor L. Evans . In Vitro Optimization of EtNBS-PDT against Hypoxic Tumor Environments with a Tiered, High-Content, 3D Model Optical Screening Platform. Molecular Pharmaceutics 2012, 9 (11) , 3171-3182.
    2. Avi Swed, Sara Eyal, Igal Madar, Hila Zohar-Kontante, Lola Weiss and Amnon Hoffman . The Role of P-Glycoprotein in Intestinal Transport versus the BBB Transport of Tetraphenylphosphonium. Molecular Pharmaceutics 2009, 6 (6) , 1883-1890.
    3. Anthony R. Ball, Gabriele Casadei, Siritron Samosorn, John B. Bremner, Frederick M. Ausubel, Terence I. Moy and Kim Lewis . Conjugating Berberine to a Multidrug Resistance Pump Inhibitor Creates an Effective Antimicrobial. ACS Chemical Biology 2006, 1 (9) , 594-600.
    4. Jane P. F. Bai,, Andrey Utis,, Gordon Crippen,, Han-Dan He,, Volker Fischer,, Robert Tullman,, He-Qun Yin,, Cheng-Pang Hsu,, Lan Jiang, and, Kin-Kai Hwang. Use of Classification Regression Tree in Predicting Oral Absorption in Humans. Journal of Chemical Information and Computer Sciences 2004, 44 (6) , 2061-2069.
    5. Jacques Ferté,, Jean-Marc Kühnel,, Geneviève Chapuis,, Yves Rolland,, Guy Lewin, and, Marc A. Schwaller. Flavonoid-Related Modulators of Multidrug Resistance:  Synthesis, Pharmacological Activity, and Structure−Activity Relationships. Journal of Medicinal Chemistry 1999, 42 (3) , 478-489.
    6. Svyatoslav S. Sokolov, Ekaterina A. Smirnova, Tatyana I. Rokitskaya, Fedor F. Severin. The Imidazolium Ionic Liquids Toxicity is Due to Their Effect on the Plasma Membrane. Biochemistry (Moscow) 2024, 89 (3) , 451-461.
    7. Raimonda Kubiliute, Indre Januskeviciene, Ruta Urbanaviciute, Kristina Daniunaite, Monika Drobniene, Valerijus Ostapenko, Rimantas Daugelavicius, Sonata Jarmalaite. Nongenotoxic ABCB1 activator tetraphenylphosphonium can contribute to doxorubicin resistance in MX-1 breast cancer cell line. Scientific Reports 2021, 11 (1)
    8. Madeline S. A. Windsor, Madleen Busse, Daniel E. Morrison, Robert W. Baker, Leila R. Hill, Louis M. Rendina. Selective delivery of remarkably high levels of gadolinium to tumour cells using an arsonium salt. Chemical Communications 2021, 57 (70) , 8806-8809.
    9. Sandra Sakalauskaitė, Valeryia Mikalayeva, Rimantas Daugelavičius. Ethidium Binding to Salmonella enterica ser. Typhimurium Cells and Salmon Sperm DNA. Molecules 2021, 26 (11) , 3386.
    10. Douglas B. Kell. A protet-based, protonic charge transfer model of energy coupling in oxidative and photosynthetic phosphorylation. 2021, 1-177.
    11. Kseniia V. Galkina, Elizaveta G. Besedina, Roman A. Zinovkin, Fedor F. Severin, Dmitry A. Knorre. Penetrating cations induce pleiotropic drug resistance in yeast. Scientific Reports 2018, 8 (1)
    12. Madleen Busse, Madeline S.A. Windsor, Alexander J. Tefay, Mingyue Kardashinsky, Jacob M. Fenton, Daniel E. Morrison, Hugh H. Harris, Louis M. Rendina. Tumor cell uptake and selectivity of gadolinium(III)-phosphonium complexes: The role of delocalisation at the phosphonium centre. Journal of Inorganic Biochemistry 2017, 177 , 313-321.
    13. Valeryia Mikalayeva, Sandra Sakalauskaitė, Rimantas Daugelavičius. Interaction of ethidium and tetraphenylphosphonium cations with Salmonella enterica cells. Medicina 2017, 53 (2) , 122-130.
    14. Dmitry A. Knorre, Elizaveta Besedina, Iuliia E. Karavaeva, Ekaterina A. Smirnova, Olga V. Markova, Fedor F. Severin, . Alkylrhodamines enhance the toxicity of clotrimazole and benzalkonium chloride by interfering with yeast pleiotropic ABC-transporters. FEMS Yeast Research 2016, 16 (4) , fow030.
    15. Dmitry A. Knorre, Olga V. Markova, Ekaterina A. Smirnova, Iuliia E. Karavaeva, Svyatoslav S. Sokolov, Fedor F. Severin. Dodecyltriphenylphosphonium inhibits multiple drug resistance in the yeast Saccharomyces cerevisiae. Biochemical and Biophysical Research Communications 2014, 450 (4) , 1481-1484.
    16. Simona Sutkuvienė, Valeryia Mikalayeva, Silvia Pavan, Federico Berti, Rimantas Daugelavičius. Evaluation of the Efficiency of Synthesized Efflux Pump Inhibitors on S almonella enterica ser. Typhimurium Cells. Chemical Biology & Drug Design 2013, 82 (4) , 438-445.
    17. Toshimitsu Okamura, Tatsuya Kikuchi, Maki Okada, Hidekatsu Wakizaka, Ming-Rong Zhang. Imaging of Activity of Multidrug Resistance–Associated Protein 1 in the Lungs. American Journal of Respiratory Cell and Molecular Biology 2013, 49 (3) , 335-340.
    18. Rimantas Daugelavičius, Andrius Buivydas, Ana Senčilo, Dennis H. Bamford. Assessment of the activity of RND-type multidrug efflux pumps in Pseudomonas aeruginosa using tetraphenylphosphonium ions. International Journal of Antimicrobial Agents 2010, 36 (3) , 234-238.
    19. Zhongming Ma, Jun Kong, Roland G. Kallen, . Studies of α-Helicity and Intersegmental Interactions in Voltage-Gated Na+ Channels: S2D4. PLoS ONE 2009, 4 (11) , e7674.
    20. Igal Madar, Yi Huang, Hayden Ravert, Susan L. Dalrymple, Nancy E. Davidson, John T. Isaacs, Robert F. Dannals, J. James Frost. Detection and Quantification of the Evolution Dynamics of Apoptosis Using the PET Voltage Sensor 18 F-Fluorobenzyl Triphenyl Phosphonium. Journal of Nuclear Medicine 2009, 50 (5) , 774-780.
    21. Michael P. Murphy. Targeting Antioxidants to Mitochondria by Conjugation to Lipophilic Cations. 2008, 575-587.
    22. Igal Madar, Hayden Ravert, Barry Nelkin, Masroor Abro, Martin Pomper, Robert Dannals, James J. Frost. Characterization of membrane potential-dependent uptake of the novel PET tracer 18F-fluorobenzyl triphenylphosphonium cation. European Journal of Nuclear Medicine and Molecular Imaging 2007, 34 (12) , 2057-2065.
    23. Michael P. Murphy, Robin A.J. Smith. Targeting Antioxidants to Mitochondria by Conjugation to Lipophilic Cations. Annual Review of Pharmacology and Toxicology 2007, 47 (1) , 629-656.
    24. Sandra Turcotte, Michel Demeule, Anthony Régina, Chantal Fournier, Julie Jodoin, Albert Moghrabi, Richard Béliveau. The Blood‐Brain Barrier: Roles of the Multidrug Resistance Transporter P‐Glycoprotein. 2006, 429-461.
    25. Zhonglin Liu, Gail D. Stevenson, Harrison H. Barrett, Lars R. Furenlid, Donald W. Wilson, George A. Kastis, Michael Bettan, James M. Woolfenden. Imaging recognition of inhibition of multidrug resistance in human breast cancer xenografts using 99mTc-labeled sestamibi and tetrofosmin. Nuclear Medicine and Biology 2005, 32 (6) , 573-583.
    26. Angela Koehler, Tilmann Alpermann, Bjarne Lauritzen, Cornelis J.F Van Noorden. Clonal xenobiotic resistance during pollution-induced toxic injury and hepatocellular carcinogenesis in liver of female flounder ( Platichthys flesus (L.)). Acta Histochemica 2004, 106 (2) , 155-170.
    27. Remigijus Didziapetris, Pranas Japertas, Alex Avdeef, Alanas Petrauskas. Classification Analysis of P-Glycoprotein Substrate Specificity. Journal of Drug Targeting 2003, 11 (7) , 391-406.
    28. Eman M El-Masry, Mohamed B Abou-Donia. Reversal of P-glycoprotein expressed in Escherichia coli leaky mutant by ascorbic acid. Life Sciences 2003, 73 (8) , 981-991.
    29. J.A. Vargas, R. Castejón, A. Varela, C. Salas, Y. Cajal, A. Durántez, M.J. Tabuenca, S. Ramón, J. Ortiz-Berrocal. Estudio de las lesiones pulmonares con 99mTc-Tetrofosmin y SPECT de tórax. Determinación de los factores que intervienen en la captación, valor diagnóstico y pronóstico. Revista Española de Medicina Nuclear 2002, 21 (2) , 99-108.
    30. D. FUSTER, M. MUÑOZ, J. PAVIA, A. PALACÍN, N. BELLET, J. J. MATEOS, F. MARTÍN, M. ORTEGA, F. J. SETOAIN, F. PONS. Quantified 99mTc-MIBI scintigraphy for predicting chemotherapy response in breast cancer patients: factors that influence the level of 99mTc-MIBI uptake. Nuclear Medicine Communications 2002, 23 (1) , 31-38.
    31. James R. Ballinger. 99m Tc‐Tetrofosmin for Functional Imaging of P‐glycoprotein Modulation In Vivo. The Journal of Clinical Pharmacology 2001, 41 (S7)
    32. Katarzyna Tkaczyk-Gobis, Jolanta Tarasiuk, Olivier Seksek, Barbara Stefanska, Edward Borowski, Arlette Garnier-Suillerot. Transport of new non-cross-resistant antitumor compounds of the benzoperimidine family in multidrug resistant cells. European Journal of Pharmacology 2001, 413 (2-3) , 131-141.
    33. Lale Kostakoglu, Stanley J. Goldsmith. Imaging Multidrug Resistance in Hematological Malignancies. Hematology 2001, 6 (2) , 111-124.
    34. Kim Lewis. Multidrug resistance: Versatile drug sensors of bacterial cells. Current Biology 1999, 9 (11) , R403-R407.
    35. David E. Reichert, Jason S. Lewis, Carolyn J. Anderson. Metal complexes as diagnostic tools. Coordination Chemistry Reviews 1999, 184 (1) , 3-66.
    36. Junmei Wang, Tingjun Hou, Lirong Chen, Xiaojie Xu. Automated docking of peptides and proteins by genetic algorithm. Chemometrics and Intelligent Laboratory Systems 1999, 45 (1-2) , 281-286.
    37. WEI-JEN SHIH, AMITA RASTOGI, VICKI STIPP, KELLY K. GROSS, JOHN J. COUPAL, SYLVIA MAGOUN. Tc-99m MIBI Thoracic SPECT for the Detection of Intrathoracic Tumor Masses. Clinical Nuclear Medicine 1998, 23 (9) , 594-600.
    38. Zsolt Szabo. Membrane Transporters. 1998, 117-131.
    39. Eitan Bibi, Rotem Edgar, Oded Béjà. [27] Functional expression of mdr and mdr-like cDNAs in Escherichia coli. 1998, 370-382.
    40. Randy M. Wadkins, Paul D. Roepe. Biophysical Aspects of P-Glycoprotein-Mediated Multidrug Resistance. 1997, 121-165.
    41. Younggil Kwon, Amrita V. Kamath, Marilyn E. Morris. Inhibitors of P-Glycoprotein-Mediated Daunomycin Transport in Rat Liver Canalicular Membrane Vesicles. Journal of Pharmaceutical Sciences 1996, 85 (9) , 935-939.
    42. B. Kurelec, S. Krča, D. Lucić. Expression of multixenobiotic resistance mechanism in a marine mussel Mytilus galloprovincialis as a biomarker of exposure to polluted environments. Comparative Biochemistry and Physiology Part C: Pharmacology, Toxicology and Endocrinology 1996, 113 (2) , 283-289.
    43. Susan E. Kane. Multidrug resistance of cancer cells. 1996, 181-252.
    44. Rodrigo Yelin, Shimon Schuldiner. The pharmacological profile of the vesicular monoamine transporter resembles that of multidrug transporters. FEBS Letters 1995, 377 (2) , 201-207.
    45. Alan E. Senior, Marwan K. Al-Shawi, Ina L. Urbatsch. ATP hydrolysis by multidrug-resistance protein from Chinese hamster ovary cells. Journal of Bioenergetics and Biomembranes 1995, 27 (1) , 31-36.
    46. Gregory L. Evans, Baofu Ni, Christine A. Hrycyna, David Chen, Suresh V. Ambudkar, Ira Pastan, Ursula A. Germann, Michael M. Gottesman. Heterologous expression systems for P-glycoprotein:E. coli, yeast, and baculovirus. Journal of Bioenergetics and Biomembranes 1995, 27 (1) , 43-52.
    47. Jm. Kühnel, J. Ferte, F. Sureau, MA. Schwaller. Spectrofluorimetric Investigation of Multidrug Resistant Versus Sensitive Cells Using JC-1. 1995, 527-530.
    48. Helmuth H.G. van Es, Herma Renkema, Hans Aerts, Erwin Schurr. Enhanced lysosomal acidification leads to increased chloroquine accumulation in CHO cells expressing the pfmdr1 gene. Molecular and Biochemical Parasitology 1994, 68 (2) , 209-219.
    49. L L Grinius, E B Goldberg. Bacterial multidrug resistance is due to a single membrane protein which functions as a drug pump.. Journal of Biological Chemistry 1994, 269 (47) , 29998-30004.
    50. H Bolhuis, D Molenaar, G Poelarends, H W van Veen, B Poolman, A J Driessen, W N Konings. Proton motive force-driven and ATP-dependent drug extrusion systems in multidrug-resistant Lactococcus lactis. Journal of Bacteriology 1994, 176 (22) , 6957-6964.
    51. SHIMON SCHULDINER, ANAT SHIRVAN, YAEL STERN‐BACH, SONIA STEINER‐MORDOCH, RODRIGO YELIN, ORLY LASKAR. From Bacterial Antibiotic Resistance to Neurotransmitter Uptake. Annals of the New York Academy of Sciences 1994, 733 (1) , 174-184.
    52. Shimon Schuldiner. A Molecular Glimpse of Vesicular Monoamine Transporters. Journal of Neurochemistry 1994, 62 (6) , 2067-2078.
    53. S. Ruetz, P. Gros. Functional expression of P-glycoproteins in secretory vesicles.. Journal of Biological Chemistry 1994, 269 (16) , 12277-12284.
    54. Helmuth H. G. van Es, Steve Karcz, Fan Chu, Alan F. Cowman, Silvia Vidal, Philippe Gros, Erwin Schurr. Expression of the Plasmodial pfmdr1 Gene in Mammalian Cells Is Associated with Increased Susceptibility to Chloroquine. Molecular and Cellular Biology 1994, 14 (4) , 2419-2428.
    55. Reinhard Krämer. Functional principles of solute transport systems: concepts and perspectives. Biochimica et Biophysica Acta (BBA) - Bioenergetics 1994, 1185 (1) , 1-34.
    56. M.K. al-Shawi, I.L. Urbatsch, A.E. Senior. Covalent inhibitors of P-glycoprotein ATPase activity.. Journal of Biological Chemistry 1994, 269 (12) , 8986-8992.
    57. J.C. Gutheil, S.R. Hart, C.P. Belani, P.W. Melera, A. Hussain. Alterations in Ca2+ transport ATPase and P-glycoprotein expression can mediate resistance to thapsigargin.. Journal of Biological Chemistry 1994, 269 (11) , 7976-7981.
    58. Doug W. Loe, Frances J. Sharom. Interaction of multidrug-resistant Chinese hamster ovary cells with the peptide ionophore gramicidin D. Biochimica et Biophysica Acta (BBA) - Biomembranes 1994, 1190 (1) , 72-84.
    59. Allan Y. Chen, Leroy F. Liu. Design of Topoisomerase Inhibitors to Overcome MDR1-Mediated Drug Resistance. 1994, 245-256.
    60. C. Minier, F. Akcha, F. Galgani. expression in Crassostrea gigas and Mytilus edulis in polluted seawater. Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 1993, 106 (4) , 1029-1036.
    61. Lynnette R. Ferguson, Bruce C. Baguley. Multidrug resistance and mutagenesis. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis 1993, 285 (1) , 79-90.
    62. J. Antoinette Killian. Gramicidin and gramicidin-lipid interactions. Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes 1992, 1113 (3-4) , 391-425.
    63. H. Grunicke, J. Hofmann. Cytotoxic and cytostatic effects of antitumor agents induced at the plasma membrane level. Pharmacology & Therapeutics 1992, 55 (1) , 1-30.

    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.

    Your Mendeley pairing has expired. Please reconnect