Inhibitory effects of quercetin derivatives on phosphodiesterase isozymes and high-affinity [3H]-rolipram binding in guinea pig tissues

Investigational New Drugs

Volumn 26, Issue 5, 2008, Pages 417-424

  Chan, Agnes L F ^a   Huang, Hui Lin ^b   Chien, Hui Chi ^b   Chen, Chi Ming ^c   Lin, Chun Nan ^d   Ko, Wun Chang ^b  

^a CHI MEI MEDICAL CENTER   (Taiwan)

^b TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^c TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^d KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

5 cyclic monophosphate (cyclic AMP); Adenosine 3 ; Asthma; Chronic obstructive pulmonary disease (COPD); High affinity rolipram binding sites (HARBSs); Phosphodiesterase isozymes 1 5 (PDE1 5); Quercetin derivatives

Indexed keywords

4 (3 BUTOXY 4 METHOXYBENZYL) 2 IMIDAZOLIDINONE; 9 (2 HYDROXY 3 NONYL)ADENINE; CYCLIC AMP; CYCLIC GMP; MILRINONE; N (3,5 DICHLORO 4 PYRIDYL) [1 (4 FLUOROBENZYL) 5 HYDROXY 3 INDOLYL]GLYOXYLIC ACID AMIDE; PHOSPHODIESTERASE I; PHOSPHODIESTERASE III; PHOSPHODIESTERASE IV; PHOSPHODIESTERASE V; QUERCETIN 3 O METHYL 5,7,3',4' O TETRAACETATE; QUERCETIN 3 O METHYL ETHER; QUERCETIN 3,5,7,3',4' O PENTAACETATE; QUERCETIN 3,7,3',4' O TETRAMETHYL ETHER; QUERCETIN 3,7,4' O TRIMETHYL ETHER; QUERCETIN DERIVATIVE; ROLIPRAM; SPLEEN EXONUCLEASE; TRITIUM; UNCLASSIFIED DRUG; VINPOCETINE; ZAPRINAST;

ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BRAIN CELL; CELL MEMBRANE; CONTROLLED STUDY; DRUG BINDING SITE; ENZYME INHIBITION; GUINEA PIG; HEART; IC 50; ISOTOPE LABELING; LUNG HOMOGENATE; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; GUINEA PIGS; ISOENZYMES; MALE; PHOSPHODIESTERASE INHIBITORS; PHOSPHORIC DIESTER HYDROLASES; QUERCETIN; ROLIPRAM;

EID: 50249116131     PISSN: 01676997     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10637-008-9114-7     Document Type: Article

References (38)

1. CK Fan 2006 Phosphodiesterase inhibitors in airways disease Eur J Pharmacol 533 110 117
2. TJ Torphy 1988 Phosphodiesterase isozymes: molecular targets for novel antiasthma agents Am J Respir Crit Care Med 157 351 370
3. SD Rybalkin C Yan KE Bornfeldt JA Beavo 2003 Cyclic GMP phosphodiesterases and regulation of smooth muscle function Circ Res 93 280 291
4. MA Giembycz 2000 Phosphodiesterase 4 inhibitors and the treatment of asthma: Where are we now and where do we go from here? Drugs 59 193 212
5. Yen KY (1971) Houttuyniae Herba. Pharmacology of commonly used chinese medicine III. National Research Institute of Chinese Medicine, Taipei, Taiwan, pp 34-35
6. P Knekt J Kumpulainen R Jarvinen H Rissanen M Heliovaara A Reunanen T Hakulinen A Aromaa 2002 Flavonoid intake and risk of chronic diseases Am J Clin Nutr 76 560 568
7. CN Lin CM Lu HC Lin FN Ko CM Teng 1995 Novel antiplatelet naphthalene from Rhamnus nakaharai J Nat Prod 58 1934 1940
8. AS Gomm M Nierenstein 1931 The exhaustive O-methylation of quercetin J Am Chem Soc 53 4408 4411
9. SM Kupchan E Bauerschmidt 1971 Cytotoxic flavonols from Baccharis sarothroides Phytochemistry 10 664 666
10. J Ferte JM Kuhnel G Chapuis Y Rolland G Lewin MA Schwaller 1999 Flavonoid-related modulators of multidrug resistance: synthesis, pharmacological activity, and structure-activity relationships J Med Chem 42 478 489
11. WC Ko MC Chen SH Wang YH Lai JH Chen CN Lin 2003 3-O-Methylquercetin more selectively inhibits phosphodiesterase subtype 3 Planta Med 69 310 315
12. WJ Thompson MM Appleman 1971 Multiple cyclic nucleotide phosphodiesterase activities from rat brain Biochemistry 10 311 316
13. HS Ahn W Crim M Romano E Sybertz B Pitts 1989 Effects of selective inhibitors on cyclic nucleotide phosphodiesterases of rabbit aorta Biochem Pharmacol 38 3331 3339
14. T Podzuweit P Nennstiel A Muller 1995 Isozyme selective inhibition of cGMP-stimulated cyclic nucleotide phosphodiesterases by erythro-9-(2-hydroxy-3- nonyl) adenine Cell Signal 7 733 738
15. SA Harrison DH Reifsnyder B Gallis GG Cadd JA Beavo 1986 Isolation and characterization of bovine cardiac muscle cGMP-inhibited phosphodiesterase: a receptor for new cardiotonic drugs Mol Pharmacol 29 506 514
16. JM O'Donnell 1993 Antidepressant-like effects of rolipram and other inhibitors of cyclic adenosine monophosphate phosphodiesterase on behavior maintained by differential reinforcement of low response rate J Pharmacol Exp Ther 264 1168 1178
17. ML Reeves BK Leigh PJ England 1987 The identification of a new cyclic nucleotide phosphodiesterase activity in human and guinea-pig cardiac ventricle. Implications for the mechanism of action of selective phosphodiesterase inhibitors Biochem J 241 535 541
18. PG Gillespie JA Beavo 1989 Inhibition and stimulation of photoreceptor phosphodiesterases by dipyridamole and M&B 22,948 Mol Pharmacol 36 773 781
19. HH Schneider R Schmiechen M Brezinski J Seidler 1986 Stereospecific binding of the antidepressant rolipram to brain protein structures Eur J Pharmacol 127 105 115
20. 3H]rolipram J Pharmacol Exp Ther 305 565 572
21. WC Ko CM Shih YH Lai JH Chen HL Huang 2004 Inhibitory effects of flavonoids on phosphodiesterase isozymes from guinea pig and their structure-activity relationships Biochem Pharmacol 68 2087 2094
22. JS Jiang HC Chien CM Chen CN Lin WC Ko 2007 Potent suppressive effects of 3-O-methylquercetin 5,7,3',4'-O-tetraacetate on ovalbumin-induced airway hyperresponsiveness Planta Med 73 1156 1162
23. 3H]-rolipram binding Biochem Pharmacol 51 949 956
24. H Masuoka M Ito M Sugioka H Kozeki T Konishi T Tanaka T Nakano 1993 Two isoforms of cGMP-inhibited cyclic nucleotide phosphodiesterases in human tissues distinguished by their responses to vesnarinone, a new cardiotonic agent Biochem Biophys Res Commun 190 412 417
25. E Moon R Lee R Near L Weintraub S Wolda A Lerner 2002 Inhibition of PDE3B augments PDE4 inhibitor-induced apoptosis in a subset of patients with chronic lymphocytic leukemia Clin Cancer Res 8 589 595
26. WH Zhu A Majluf-Cruz GA Omburo 1998 Cyclic AMP-specific phosphodiesterase inhibitor rolipram and RO-20-1724 promoted apoptosis in HL60 promyelocytic leukemic cells via cyclic AMP-independent mechanism Life Sci 63 265 274
27. D Marko K Romanakis H Zankl G Furstenberger B Steinbauer G Eisenbrand 1998 Induction of apoptosis by an inhibitor of cAMP-specific PDE in malignant murine carcinoma cells overexpressing PDE activity in comparison to their nonmalignant counterparts Cell Biochem Biophys 28 75 101
28. DH Kim A Lerner 1998 Type 4 cyclic adenosine monophosphate phosphodiesterase as a therapeutic target in chronic lymphocytic leukemia Blood 92 2484 2494
29. B Siegmund J Welsch F Loher G Meinhardt B Emmerich S Endres A Eigler 2001 Phosphodiesterase type 4 inhibitor suppresses expression of anti-apoptotic members of the Bcl-2 family in B-CLL cells and induces caspase-dependent apoptosis Leukemia 15 1564 1571
30. M Aklilu HL Kindler RC Donehower S Mani EE Vokes 2003 Phase II study of flavopiridol in patients with advanced colorectal cancer Ann Oncol 14 1270 1273
31. JE Karp DD Ross W Yang ML Tidwell Y Wei J Greer T Nakanishi JJ Wright AD Colevas 2003 Timed sequential therapy of acute leukemia with flavopiridol: in vitro model for a phase I clinical trial Clin Cancer Res 9 307 315
32. AM Senderowicz EA Sausville 2000 Preclinical and clinical development of cyclin-dependent kinase modulators J Natl Cancer Inst 92 376 387
33. AM Senderowicz 2003 Small-molecule cyclin-dependent kinase modulators Oncogene 22 6609 6620
34. BJ Lipworth 2005 Phosphodiesterase-4 inhibitors for asthma and chronic obstructive pulmonary disease Lancet 365 167 175
35. A Hatzelmann C Schudt 2001 Anti-inflammatory and immunomodulatory potential of the novel PDE4 inhibitor roflumilast in vitro J Pharmacol Exp Ther 297 267 279
36. R Draheim U Egerland C Rundfeldt 2004 Anti-inflammatory potential of the selective phosphodiesterase 4 inhibitor N-(3,5-dichloro-pyrid-4-yl)-[1-(4- fluorobenzyl)-5-hydroxy-indole-3-yl]-glyoxylic acid amide (AWD 12-281), in human cell preparations J Pharmacol Exp Ther 308 555 563
37. H Kuss N Hoefgen S Johanssen T Kronbach C Rundfeldt 2003 In vivo efficacy in airway disease models of N-(3,5-dichloropyrid-4-yl)-[1-(4-fluorobenzyl)-5- hydroxy-indole-3-yl]-glyoxylic acid amide (AWD 12-281), a selective phosphodiesterase 4 inhibitor for inhaled administration J Pharmacol Exp Ther 307 373 385
38. J Hoppmann W Baumer C Galetzka N Hofgen M Kietzmann C Rundfeldt 2005 The phosphodiesterase 4 inhibitor AWD 12-281 is active in a new guinea-pig model of allergic skin inflammation predictive of human skin penetration and suppresses both Th1 and Th2 cytokines in mice J Pharm Pharmacol 57 1609 1617