Comparative studies of anthraquinone- and anthracene-tetraamines as blockers of N-methyl-D-aspartate receptors

Journal of Pharmacology and Experimental Therapeutics

Volumn 320, Issue 1, 2007, Pages 47-55

  Jin, Lihua ^a   Sugiyama, Hiromi ^a   Takigawa, Miki ^a   Katagiri, Daisuke ^a   Tomitori, Hideyuki ^b   Nishimura, Kazuhiro ^a   Kaur, Navneet ^c   Phanstiel IV, Otto ^c   Kitajima, Mariko ^a   Takayama, Hiromitsu ^a   Okawara, Tadashi ^d   Williams, Keith ^e   Kashiwagi, Keiko ^b   Igarashi, Kazuei ^a  

^a CHIBA UNIVERSITY   (Japan)

^b CHIBA INSTITUTE OF SCIENCE   (Japan)

^c UNIVERSITY OF CENTRAL FLORIDA   (United States)

^d KUMAMOTO UNIVERSITY   (Japan)

^e SUNY DOWNSTATE MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANT 343; ANT 444; ANTHRACENE DERIVATIVE; ANTHRAQUINONE DERIVATIVE; AQ 343; AQ 444; N 1 (9 ANTHRACENYLMETHYL)HOMOSPERMINE; N 1 (9 ANTHRACENYLMETHYL)SPERMINE; N 1 (ANTHRAQUINONE 2 CARBONYL)SPERMINE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; POLYAMINE; SPERMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHANNEL GATING; CONTROLLED STUDY; ELECTRIC POTENTIAL; GENE MUTATION; MEMBRANE POTENTIAL; NONHUMAN; PRIORITY JOURNAL; WILD TYPE;

ANIMALS; ANTHRACENES; ANTHRAQUINONES; DIZOCILPINE MALEATE; EXCITATORY AMINO ACID ANTAGONISTS; FEMALE; MICE; MUTAGENESIS, SITE-DIRECTED; POLYAMINES; RECEPTORS, N-METHYL-D-ASPARTATE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33845873922     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.106.110528     Document Type: Article

References (40)

1. Benveniste M and Mayer ML (1993) Multiple effects of spermine on N-methyl-D-aspartic acid receptor responses of rat cultured hippocampal neurons. J Physiol (Lond) 464:131-163.
2. 1-(n- octanesulfonyl)-spermine, novel glutamate receptor antagonists: block and permeation of N-methyl-D-aspartate receptors. Mol Pharmacol 51:861-871.
3. Chen H-SV and Lipton SA (2005) Pharmacological implications of two distinct mechanisms of interaction of memantine with N-methyl-D- aspartate-gated channels. J Pharmacol Exp Ther 314:961-971.
4. Choi DW (1988) Glutamate neurotoxicity and diseases of the nervous system. Neuron 1:623-634.
5. Cox RA, Druet LM, Klansner AE, Modro TA, Wan P, and Yates K (1981) Protonation acidity constants for some benzyamides, acetamides, and lactams. Can J Chem/Rev Can Chim 59:1568-1573.
6. Dingledine R, Borges K, Bowie D, and Traynelis SF (1999) The glutamate receptor ion channels. Pharmacol Rev 51:7-61.
7. + conduction and selectivity. Science (Wash DC) 280:69-77.
8. Hidai Y, Kan T, and Fukuyama T (2000) Total synthesis of polyamine toxin H0-416b and Agel-489 using a 2-nitrobenzenesulfonamide strategy. Chem Pharm Bull 48:1570-1576.
9. Ho SN, Hunt HD, Horton RM, Pullen JK, and Pease LR (1989) Site-directed mutagenesis by overlap extension using the polymerase chain reaction. Gene (Amst) 77:51-59.
10. Hollmann M and Heinemann S (1994) Cloned glutamate receptors. Annu Rev Neurosci 17:31-108.
11. Huettner JE and Bean BP (1988) Block of N-methyl-D- aspartate-activated current by the anticonvalsant MK-801: selective binding to open channels. Proc Natl Acad Sci USA 85:1307-1311.
12. Igarashi K, Shirahata A, Pahk AJ, Kashiwagi K, and Williams K (1997) Benzylpolyamines: novel, potent N-methyl-D-aspartate receptor antagonists. J Pharmacol Exp Ther 283:533-540.
13. Igarashi K and Williams K (1995) Antagonist properties of polyamines and bis(ethyl) polyamines at N-methyl-D-aspartate receptors. J Pharmacol Exp Ther 272:1101-1109.
14. Ikeda K, Nagasawa M, Mori H, Araki K, Sakimura K, Watanabe M, Inoue Y, and Mishina M (1992) Cloning and expression of the 4 subunit of the NMDA receptor channel. FEBS Lett 313:34-38.
15. Kashiwagi K, Masuko T, Nguyen CD, Kuno T, Tanaka I, Igarashi K, and Williams K (2002) Channel blockers acting at N-methyl-D- aspartate receptors: differential effects of mutations in the vestibule and ion channel pore. Mol Pharmacol 61:533-545.
16. Kashiwagi K, Pahk AJ, Masuko T, Igarashi K, and Williams K (1997) Block and modulation of N-methyl-D-aspartate receptors by polyamines and protons: role of amino acid residues in the transmembrane and pore-forming regions of NR1 and NR2 subunits. Mol Pharmacol 52:701-713.
17. Kashiwagi K, Tanaka I, Tamura M, Sugiyama H, Okawara T, Otsuka M, Sabado TN, Williams K, and Igarashi K (2004) Anthraquinone polyamines: novel channel blockers to study N-methyl-D-aspartate receptors. J Pharmacol Exp Ther 309:884-893.
18. Kuner T, Wollmuth LP, Karlin A, Seeburg PH, and Sakmann B (1996) Structure of the NMDA receptor channel M2 segment inferred from the accessibility of substituted cysteines. Neuron 17:343-352.
19. Kutsuwada T, Kashiwabuchi N, Mori H, Sakimura K, Kushiya E, Araki K, Meguro H, Masaki H, Kumanishi T, Arakawa M, et al. (1992) Molecular diversity of the NMDA receptor channel. Nature (Lond) 358:36-41.
20. Lipton SA (2005) The molecular basis of memantine action in Alzheimer's disease and other neurologic disorders: low-affinity, uncompetitive antagonism. Curr Alzheimer Res 2:155-165.
21. Masuko T, Kashiwagi K, Kuno T, Nguyen ND, Pahk AJ, Fukuchi J, Igarashi K, and Williams K (1999) A regulatory domain (R1-R2) in the amino terminus of the N-methyl-D-aspartate receptor: effects of spermine, protons, and ifenprodil, and structural similarity to bacterial leucine/isoleucine/valine binding protein. Mol Pharmacol 55:957-969.
22. Monyer H, Sprengel R, Schoepfer R, Herb A, Higuchi M, Lomeli H, Burnashev N, Sakmann B, and Seeburg PH (1992) Heteromeric NMDA receptors: molecular and functional distinction of subtypes. Science (Wash DC) 256:1217-1221.
23. Moriyoshi K, Masu M, Ishii T, Shigemoto R, Mizuno N, and Nakanishi S (1991) Molecular cloning and characterization of the rat NMDA receptor. Nature (Lond) 354:31-37.
24. Parsons CG, Danysz W, Bartmann A, Spielmanns P, Frankiewicz T, Hesselink M, Eilbacher B, and Quack G (1999) Amino-alkyl-cyclohexanes are novel uncompetitive NMDA receptor antagonists with strong voltage-dependency and fast blocking kinetics: in vitro and in vivo characterization. Neuropharmacology 38:85-108.
25. Reisberg B, Doody R, Stoffler A, Schmitt F, Ferris S, and Mobius HJ, for the memantine study group (2003) Memantine in moderate-to-severe Alzheimer's disease. N Engl J Med 348:1333-1341.
26. Rodríguez-Paz JM, Anantharam V, and Treistman SN (1995) Block of the N-methyl-D-aspartate receptor by phencyclidine-like drugs is influenced by alternative splicing. Neurosci Lett 190:147-150.
27. Rogawski MA (1992) The NMDA receptor, NMDA antagonists and epilepsy therapy. A status report. Drugs 44:279-292.
28. Sakimura K, Bujo H, Kushiya E, Araki K, Yamazaki M, Yamazaki M, Meguro H, Warashina A, Numa S, and Mishina M (1990) Functional expression from cloned cDNAs of glutamate receptor species responsive to kainate and quisqualate. FEBS Lett 272:73-80.
29. 2+ and channel blockers by a single amino acid substitution in the N-methyl-D-aspartate receptor. J Biol Chem 268:410-415.
30. Sobolevsky AI, Rooney L, and Wollmuth LP (2002) Staggering of subunits in NMDAR channels. Biophys J 83:3304-3314.
31. Tai K-K, Blondelle SE, Ostresh JM, Houghten RA, and Montal M (2001) An Nmethyl-D-aspartate receptor channel blocker with neuroprotective activity. Proc Natl Acad Sci USA 98:3519-3524.
32. Wang C, Delcros J-G, Biggerstaff J, and Phanstiel OIV (2003) Molecular requirements for targeting the polyamine transport system. Synthesis and biological evaluation of polyamine-anthracene conjugates. J Med Chem 46:2672-2682.
33. Wang J, Wolf RM, Caldwell JW, Kollamn PA, and Case DA (2004) Development and testing of a general amber force field. J Comput Chem 25:1157-1174.
34. Watanabe M, Inoue Y, Sakimura K, and Mishina M (1992) Developmental changes in distribution of NMDA receptor channel subunit mRNAs. Neuroreport 3:1138-1140.
35. Williams K (1993) Ifenprodil discriminates subtypes of the N-methyl-D-aspartate receptor: selectivity and mechanisms at recombinant heteromeric receptors. Mol Pharmacol 44:851-859.
36. Williams K (1997) Interactions of polyamines with ion channels. Biochem J 325: 289-297.
37. 2+. Mol Pharmacol 53:933-941.
38. Wollmuth LP, Kuner T, Seeburg PH, and Sakmann B (1996) Differential contribution of the NR1- and NR2A-subunits to the selectivity filter of recombinant NMDA receptor channels. J Physiol (Lond) 491:779-797.
39. Yuan H, Erreger K, Dravid SM, and Traynelis SF (2005) Conserved structural and functional control of N-methyl-D-aspartate receptor gating by transmembrane domain M3. J Biol Chem 280:29708-29716.
40. Zhang D-D, Huang N-J, Xue L, and Huang Y-M (1987) β-Cyclodextrin- catalyzed effects on the hydrolysis of esters of aromatic acids. J Inclusion Phenomena Macrocyclic Chem 5:443-447.