Five amino acids in the innermost cavity of the substrate binding cleft of organic cation transporter 1 interact with extracellular and intracellular corticosterone

Molecular Pharmacology

Volumn 76, Issue 2, 2009, Pages 275-289

  Volk, Christopher ^a   Gorboulev, Valentin ^a   Kotzsch, Alexander ^a   Müller, Thomas D ^a   Koepsell, Hermann ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE; ASPARTIC ACID; CORTICOSTERONE; GLUTAMIC ACID; LEUCINE; MUTANT PROTEIN; ORGANIC CATION TRANSPORTER 1; PHENYLALANINE; TETRYLAMMONIUM; TRYPTOPHAN;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ANIMAL CELL; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG PROTEIN BINDING; EPITHELIUM CELL; HORMONE ACTION; HORMONE PROTEIN COMPLEX; HUMAN; HUMAN CELL; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; OOCYTE; PRIORITY JOURNAL; PROTEIN CONFORMATION; SIMULATION; XENOPUS LAEVIS;

ALANINE; AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; AMINO ACIDS; ANIMALS; CORTICOSTERONE; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; HYDROGEN BONDING; HYDROPHOBICITY; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; OOCYTES; ORGANIC CATION TRANSPORTER 1; PATCH-CLAMP TECHNIQUES; PHENYLALANINE; POINT MUTATION; PROTEIN STRUCTURE, SECONDARY; RATS; SEQUENCE HOMOLOGY, AMINO ACID; SUBSTRATE SPECIFICITY; TYROSINE; XENOPUS LAEVIS;

EID: 67650786266     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.109.054783     Document Type: Article

References (24)

1. Abramson J, Smirnova I, Kasho V, Verner G, Kaback HR, and Iwata S (2003) Structure and mechanism of the lactose permease of Escherichia coli. Science 301:610-615. (Pubitemid 36927939)
2. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, et al. (2001) Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol 281:F454-F468. (Pubitemid 32885130)
3. Ermolova N, Madhvani RV, and Kaback HR (2006) Site-directed alkylation of cysteine replacements in the lactose permease of Escherichia coli: helices I, III, VI, and XI. Biochemistry 45:4182-4189.
4. Gorboulev V, Shatskaya N, Volk C, and Koepsell H (2005) Subtype-specific affinity for corticosterone of rat organic cation transporters rOCT1 and rOCT2 depends on three amino acids within the substrate binding region. Mol Pharmacol 67:1612-1619. (Pubitemid 40594160)
5. Gorboulev V, Volk C, Arndt P, Akhoundova A, and Koepsell H (1999) Selectivity of the polyspecific cation transporter rOCT1 is changed by mutation of aspartate 475 to glutamate. Mol Pharmacol 56:1254-1261.
6. Gorbunov D, Gorboulev V, Shatskaya N, Mueller T, Bamberg E, Friedrich T, and Koepsell H (2008) High-affinity cation binding to organic cation transporter 1 induces movement of helix 11 and blocks transport after mutations in a modeled interaction domain between two helices. Mol Pharmacol 73:50-61. (Pubitemid 350294196)
7. Ho SN, Hunt HD, Horton RM, Pullen JK, and Pease LR (1989) Site-directed mutagenesis by overlap extension using the polymerase chain reaction. Gene 77:51-59. (Pubitemid 19125653)
8. Holyoake J and Sansom MSP (2007) Conformational change in an MFS protein: MD simulations of LacY. Structure 15:873-884. (Pubitemid 47042433)
9. Kaback HR, Dunten R, Frillingos S, Venkatesan P, Kwaw I, Zhang W, and Ermolova N (2007) Site-directed alkylation and the alternating access model for LacY. Proc Natl Acad Sci U S A 104:491-494. (Pubitemid 46123053)
10. Koepsell H, Lips K, and Volk C (2007) Polyspecific organic cation transporters: structure, function, physiological roles, and biopharmaceutical implications. Pharm Res 24:1227-1251. (Pubitemid 46876495)
11. Lips KS, Volk C, Schmitt BM, Pfeil U, Arndt P, Miska D, Ermert L, Kummer W, and Koepsell H (2005) Polyspecific cation transporters mediate luminal release of acetylcholine from bronchial epithelium. Am J Respir Cell Mol Biol 33:79-88. (Pubitemid 40961017)
12. Majumdar DS, Smirnova I, Kasho V, Nir E, Kong X, Weiss S, and Kaback HR (2007) Single-molecule FRET reveals sugar-induced conformational dynamics in LacY. Proc Natl Acad Sci U S A 104:12640-12645. (Pubitemid 47255207)
13. Mehrens T, Lelleck S, Cetinkaya I, Knollmann M, Hohage H, Gorboulev V, Bokník P, Koepsell H, and Schlatter E (2000) The affinity of the organic cation transporter rOCT1 is increased by protein kinase C-dependent phosphorylation. J Am Soc Nephrol 11:1216-1224. (Pubitemid 30416217)
14. Minuesa G, Volk C, Molina-Arcas M, Gorboulev V, Erkizia I, Arndt P, Clotet B, Pastor-Anglada M, Koepsell H, and Martinez-Picado J (2009) Transport of lamivudine [(-)-β-L-2′,3′-dideoxy-3′-thiacytidine] and high-affinity interaction of nucleoside reverse transcriptase inhibitors with human organic cation transporters 1, 2, and 3. J Pharmacol Exp Ther 329:252-261.
15. Nagel G, Volk C, Friedrich T, Ulzheimer JC, Bamberg E, and Koepsell H (1997) A reevaluation of substrate specificity of the rat cation transporter rOCT1. J Biol Chem 272:31953-31956. (Pubitemid 28011860)
16. Popp C, Gorboulev V, Müller TD, Gorbunov D, Shatskaya N, and Koepsell H (2005) Amino acids critical for substrate affinity of rat organic cation transporter 1 line the substrate binding region in a model derived from the tertiary structure of lactose permease. Mol Pharmacol 67:1600-1611. (Pubitemid 40594159)
17. Rarey M, Kramer B, and Lengauer T (1999) The particle concept: placing discrete water molecules during protein-ligand docking predictions. Proteins 34:17-28. (Pubitemid 29019529)
18. Rarey M, Kramer B, Lengauer T, and Klebe G (1996) A fast flexible docking method using an incremental construction algorithm. J Mol Biol 261:470-489. (Pubitemid 26335901)
19. Reitman ML and Schadt EE (2007) Pharmacogenetics of metformin response: a step in the path toward personalized medicine. J Clin Invest 117:1226-1229. (Pubitemid 46718410)
20. Schmitt BM, Gorbunov D, Schlachtbauer P, Egenberger B, Gorboulev V, Wischmeyer E, Müller T, and Koepsell H (2009) Charge-to-substrate ratio during organic cation uptake by rat OCT2 is voltage dependent and altered by exchange of glutamate 448 by glutamine. Am J Physiol Renal Physiol 296:F709-F722.
21. Smirnova I, Kasho V, Choe JY, Altenbach C, Hubbell WL, and Kaback HR (2007) Sugar binding induces an outward facing conformation of LacY. Proc Natl Acad Sci U S A 104:16504-16509. (Pubitemid 350211048)
22. Smirnova IN, Kasho VN, and Kaback HR (2006) Direct sugar binding to LacY measured by resonance energy transfer. Biochemistry 45:15279-15287.
23. Sturm A, Gorboulev V, Gorbunov D, Keller T, Volk C, Schmitt BM, Schlachtbauer P, Ciarimboli G, and Koepsell H (2007) Identification of cysteines in rat organic cation transporters rOCT1 (C322, C451) and rOCT2 (C451) critical for transport activity and substrate affinity. Am J Physiol Renal Physiol 293:F767-F779. (Pubitemid 47403347)
24. Volk C, Gorboulev V, Budiman T, Nagel G, and Koepsell H (2003) Different affinities of inhibitors to the outwardly and inwardly directed substrate binding site of organic cation transporter 2. Mol Pharmacol 64:1037-1047. (Pubitemid 37310736)