Erratum: Antiallergic activity profile in vitro RBL-2H3 and in vivo passive cutaneous anaphylaxis mouse model of new sila-substituted 1,3,4-oxadiazoles (Journal of Medicinal Chemistry (2012) 55 (6438-6444) DOI:10.1021/jm300421h);Antiallergic activity profile in vitro RBL-2H3 and in vivo passive cutaneous anaphylaxis mouse model of new sila-substituted 1,3,4-oxadiazoles

Journal of Medicinal Chemistry

Volumn 55, Issue 14, 2012, Pages 6438-6444

  Dinneswara Reddy, Guda ^a   Park, Sae Jin ^a   Cho, Hyeon Mo ^a   Kim, Tack Joong ^a   Lee, Myong Euy ^a  

^a Yonsei University Wonju   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; 2 (4 CHLOROPHENYL) 5 (NEOPENTYLSULFONYLMETHYL)1,3,4 OXADIAZOLE; 2 (4 CHLOROPHENYL) 5 [[(TRIMETHYLSILYL)METHYLSULFONYL]METHYL] 1,3,4 OXADIAZOLE; 2,4 DINITROPHENOL; ANTIALLERGIC AGENT; BETA N ACETYLHEXOSAMINIDASE; DIPHENHYDRAMINE; HUMAN SERUM ALBUMIN; MESSENGER RNA; PROTEIN KINASE B; SILICON DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; DRUG SYNTHESIS; IN VITRO STUDY; IN VIVO STUDY; MALE; MAST CELL DEGRANULATION; MOUSE; NONHUMAN; PASSIVE SKIN ANAPHYLAXIS; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION; RAT;

EID: 84864240189     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3011367     Document Type: Erratum

References (39)

1. Grammatikos, A. P. The genetic and environmental basis of atopic diseases Ann. Med. 2008, 40 (7) 482-495
2. Bindslev-Jensen, C. Changing Definitions of Allergy. In Allergic Diseases and the Environment; Isolauri, E.; Walker, W. A., Eds.; Karger, AG: Basel, Switzerland, 2004; Vol 53, pp 27-32.
3. Lee, H. S.; Hong, K. H.; Yoon, C. H.; Kim, J. M.; Kim, S. M. Effect of Korean turbid rice wine (Takju) lees extract on blood glucose in the db/db mouse Korean J. Food Culture 2009, 24, 219-223
4. Nishida, K.; Yamasaki, S.; Ito, Y.; Kabu, K.; Hattori, K.; Tezuka, T.; Nishizumi, H.; Kitamura, D.; Goitsuka, R.; Geha, R. S.; Yamamoto, T.; Yagi, T.; Hirano, T. FcepsilonRI-mediated mast cell degranulation requires calcium independent microtubule-dependent translocation of granules to the plasma membrane J. Cell Biol. 2005, 170, 115-126
5. Rivera, J.; Gilfillan, A. M. Molecular regulation of mast cell activation J. Allergy Clin. Immunol. 2006, 117, 1214-1225
6. Gilfillan, A. M.; Tkaczyk, C. Integrated signalling pathways for mast-cell activation Nat. Rev. Immunol. 2006, 6, 218-230
7. Kambayashi, T.; Koretzky, G. A. Proximal signaling events in FcεRI-mediated mast cell activation J. Allergy Clin. Immunol. 2007, 119, 544-552
8. Kraft, S.; Kinet, J. P. New developments in FcεRI regulation, function and inhibition Nat. Rev. Immunol. 2007, 7, 365-378
9. Rivera, J.; Olivera, A. Src family kinases and lipid mediators in control of allergic inflammation Immunol. Rev. 2007, 217, 255-268
10. Granberg, M.; Fowler, C. J.; Jacobsson, S. O. Effects of the cannabimimetic fatty acid derivatives 2-arachidonoylglycerol, anandamide, palmitoylethanolamide and methanandamide upon IgE-dependent antigen-induced betahexosaminidase, serotonin and TNF alpha release from rat RBL-2H3 basophilic leukaemic cells Naunyn-Schmiedeberg's Arch. Pharmacol 2001, 364, 66-73
11. Musser, J. H.; Brown, R. E.; Loev, B.; Bailey, K.; Jones, H.; Kahen, R.; Huang, F.; Khandwala, A.; Leibowitz, M.; Sonnino-Goldman, P.; Donigi-Ruzza, D. Synthesis of 2-(2,3-dihydro-2-oxo-1,3,4-oxadiazol-5-yl)benzo heterocycles. A novel series of orally active antiallergic agents J. Med. Chem. 1984, 27, 121-125
12. Tan, T. M. C.; Chena, Y.; Kong, K. H.; Bai, J.; Li, Y.; Lim, S. G.; Ang, T. H.; Lam, Y. Synthesis and the biological evaluation of 2- benzenesulfonylalkyl-5-substituted-sulfanyl-[1,3,4]-oxadiazoles as potential anti-hepatitis B virus agents Antiviral Res. 2006, 71, 7-14
13. Akhter, M.; Husain, A.; Azad, B.; Ajmal, M. Aroylpropionic acid based 2,5-disubstituted-1,3,4-oxadiazoles: synthesis and their anti-inflammatory and analgesic activities Eur. J. Med. Chem. 2009, 44, 2372-2378
14. Aboraia, A. S.; Abdel-Rahman, H. M.; Mahfouz, N. M.; EL-Gendy, M. A. Novel 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives: promising anticancer agents Bioorg. Med. Chem. 2006, 14, 1236-1246
15. Kumar, D.; Sundaree, S.; Johnson, E. O.; Shah, K. An efficient synthesis and biological study of novel indolyl-1,3,4-oxadiazoles as potent anticancer agents Bioorg. Med. Chem. Lett. 2009, 19, 4492-4494
16. Prakash, O.; Kumar, M.; Kumar, R.; Sharma, C.; Aneja, K. R. Hypervalent iodine(III) mediated synthesis of novel unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles as antibacterial and antifungal agents Eur. J. Med. Chem. 2010, 45, 4252-4257
17. Arkles, B. Look what you can make out of silicones CHEMTECH 1983, 13, 542-555
18. Tacke, R.; Reichel, D.; Kropfgans, M.; Jones, P. G.; Mutschler, E.; Gross, J.; Hou, X.; Waelbroeck, M.; Lambrecht, G. Biological recognition of enantiomeric silanes: syntheses and antimuscarinic properties of optically active (2-aminoethyl)cyclohexyl(hydroxymethy1)phenylsilanes and related quaternary ammonium derivatives Organometallics 1995, 14, 251-262
19. Lambrecht, G.; Feifel, R.; Wagner-Röder, M.; Strohmann, C.; Zilch, H.; Tacke, R.; Waelbroeck, M.; Christophe, J.; Boddeke, H.; Mutschler, E. Affinity profiles of hexahydro-sila-difenidol analogues at muscarinic receptor subtypes Eur. J. Pharmacol. 1989, 168 (1) 71-80
20. Lambrecht, G.; Feifel, R.; Moser, U.; Wagner-Roder, M.; Choo, L. K.; Camus, J.; Tastenoy, M.; Waelbroeck, M.; Strohmann, C.; Tacke, R.; Rodrigues de Miranda, J. F.; Christophe, J.; Mutschler, E. Pharmacology of hexahydro-difenidol, hexahydro-sila-difenidol and related selective muscarinic antagonist Trends Pharmacol. Sci., Suppl. 1989, 10, 60-64
21. Kenney, M. E.; Oleinich, N. L.; Rihter, B. D.; Li, Y.-S. Phthalocyanine Photosensitizers for Photodynamic Therapy and Methods for Their Synthesis and Use. U.S. Patent 5484778, 1996.
22. Li, Y. S.; Kenney, M. E. Novel Methods of Synthesis of Phthalocyanine Compounds. U.S. Patent 5763602, 1998.
23. Cheng, G.; Hao, G.; Wu, H.; Li, Y.-S.; Kenney, M. E. Methods for Inserting Silicon into Phthalocyanines. U.S. Patent 5872248, 1999.
24. Farkas, S. Silperisone: a centrally acting muscle relaxant CNS Drug Rev. 2006, 12, 218-235
25. Rizvi, N. A.; Marshall, J. L.; Ness, E.; Hawkins, M. J.; Kessler, C.; Jacobs, H.; Brenckman, W. D., Jr.; Lee, J. S.; Petros, W.; Hong, W. K.; Kurie, J. M. Initial clinical trial of oral TAC-101, a novel retinoic acid receptor alpha selective retinoid, in patients with advanced cancer J. Clin. Oncol. 2002, 20, 3522-3532
26. Daud, A.; Valkov, N.; Centeno, B.; Derderian, J.; Sullivan, P.; Munster, P.; Urbas, P.; Deconti, R. C.; Berghorn, E.; Liu, Z.; Hausheer, F.; Sullivan, D. Phase II trial of karenitecin in patients with malignant melanoma: clinical and translational study Clin. Cancer Res. 2005, 11, 3009-3016
27. Reddy, M. V. R.; Reddy, S. Synthesis of α, β-unsaturated suflones Acta Chim. Hung. 1984, 115, 269-271
28. Reddy, D. B.; Reddy, N. S.; Reddy, M. V. R.; Balasubramanyam, S. Preparation of styryl benzyl sulfones and 1,2-bis-(styrylsulfonyl-methyl)-4,5- dimethylbenzenes Org. Prep. Proced. Int. 1988, 20, 205-212
29. Padmavathi, V.; Dinneswara Reddy, G.; Nagi Reddy, S.; Mahesh, K. Synthesis and biological activity of 2-(bis((1,3,4-oxadiazolyl/1,3,4- thiadiazolyl)methylthio)methylene)-malononitriles Eur. J. Med. Chem. 2011, 46, 1367-1373
30. Weidmann, B. (Trimethylsilyl)alanine: a metabolically stable bio-isostere for phenylalanine Chimia 1992, 46, 312-313
31. Kalesnikoff, J. S.; Galli, J. New developments in mast cell biology Nat. Immunol. 2008, 9, 1215-1223
32. Kayvan, H. R.; Martin, M.; Marcus, M. Mast cells: makers and breakers of allergic inflammation Curr. Opin. Allergy Clin. Immunol. 2009, 9, 427-430
33. Passante, E.; Frankish, N. The RBL-2H3 cell line: its provenance and suitability as a model for the mast cell Inflammation Res. 2009, 58, 737-745
34. Sho, Y.; Takashi, S. Progress in allergy signal research on mast cells: signal regulation of multiple mast cell responses through FcεRI J. Pharmacol. Sci 2008, 106, 336-340
35. Metcalf, D. The molecular control of cell division, differentiation, commitment and maturation in hematopoietic cells Nature 1989, 339, 27-30
36. Mills, J. S.; Showell, G. A. Exploitation of silicon medicinal chemistry in drug discovery Expert Opin. Invst. Drugs 2004, 13 (9) 1149-1157
37. Gately, S.; West, W. Novel therapeutics with enhanced biological activity generated by the strategic introduction of silicon isosteres into known drug scaffolds Drug. Dev. Res 2007, 68, 156-163
38. Andrade, M. V.; Hiragun., T.; Beaven, M. A. Dexamethasone suppresses antigen-induced activation of phosphatidylinositol 3-kinase and downstream responses in mast cells J. Immunol. 2004, 172, 7254-7262
39. Kim, J. W.; Lee, J. H.; Hwang, B. Y.; Mun, S. H.; Ko, N. Y.; Kim, D. K.; Kim, B.; Kim, H. S.; Kim, Y. M.; Choi, W. S. Morin inhibits Fyn kinase in mast cells and IgE-mediated type I hypersensitivity response in vivo Biochem. Pharmacol. 2009, 77, 1506-1512