A three-dimensional pharmacophore modelling of ITK inhibitors and virtual screening for novel inhibitors

References

• Smith , CIE , Islam , TC , Mattsson , PT , Mohamed , AJ , Nore , BF and Vihinen , M . 2001 . The Tec family of cytoplasmic tyrosine kinases: Mammalian Btk, Bmx, Itk, Txk and homologs in other species . Bioessays , 23 : 436 – 446 .
   PubMed Web of Science ®Google Scholar
• Liao , XC and Littman , DR . 1995 . Altered T cell receptor signaling and disrupted T cell development in mice lacking Itk . Immunity , 3 : 757 – 769 .
   PubMed Web of Science ®Google Scholar
• Kanner , SB and Perez-Villar , JJ . 2003 . Altering T-cell activation by targeting the multidomain tyrosine kinase Itk . Trends Immunol. , 24 : 249 – 253 .
   PubMedGoogle Scholar
• Cheetham , GMT . 2004 . Novel protein kinases and molecular mechanisms of autoinhibition . Curr. Opin. Struc. Biol. , 14 : 700 – 705 .
   PubMed Web of Science ®Google Scholar
• Ohashi , PS . 2002 . T-cell signaling and autoimmunity: Molecular mechanisms of disease . Nat. Rev. Immunol. , 2 : 427 – 438 .
   PubMed Web of Science ®Google Scholar
• Lin , TA , McIntyre , KW , Das , J , Liu , C , O’Day , KD , Penhallow , B , Hung , CY , Whitney , GS , Shuster , DJ , Yang , X , Townsend , R , Postelnek , J , Spergel , SH , Lin , J , Moquin , RV , Furch , JA , Kamath , AV , Zhang , H , Marathe , PH , Perez-Villar , JJ , Doweyko , A , Killar , L , Dodd , JH , Barrish , JC , Wityak , J and Kanner , SB . 2004 . Selective Itk inhibitors block T-cell activation and murine lung inflammation . Biochemistry , 43 : 11056 – 11062 .
   PubMed Web of Science ®Google Scholar
• Schaeffer , E , Yap , G , Lewis , C , Czar , M , McVicar , D , Cheever , A , Sher , A and Schwartzberg , P . 2001 . Mutation of Tec family kinases alters T helper cell differentiation . Nat. Immunol. , 2 : 1183 – 1188 .
   PubMed Web of Science ®Google Scholar
• Schaeffer , E . 1999 . Requirement for Tec kinases Rlk and Itk in T cell receptor signaling and immunity . Science , 284 : 638 – 641 .
   PubMed Web of Science ®Google Scholar
• Fowell , D , Shinkai , K , Liao , X , Beebe , A , Coffman , R , Littman , D and Locksley , R . 1999 . Impaired NFATc translocation and failure of Th2 development in Itk deficient CD4 T cells . Immunity , 11 : 399 – 409 .
   PubMed Web of Science ®Google Scholar
• Mueller , C and August , A . 2003 . Attenuation of immunological symptoms of allergic asthma in mice lacking the tyrosine kinase ITK . J. Immunol. , 170 : 5056 – 5063 .
   PubMed Web of Science ®Google Scholar
• Liu , K , Bunnell , S , Gurniak , C and Berg , L . 1998 . T cell receptor-initiated calcium release is uncoupled from capacitative calcium entry in Itk-deficient T cells . J. Exp. Med. , 18 : 1721 – 1727 .
   Google Scholar
• Miller , A , Wilcox , H , Lai , Z and Berg , L . 2004 . Signaling through Itk promotes T helper 2 differentiation via negative regulation of T-bet . Immunity , 21 : 67 – 80 .
   PubMed Web of Science ®Google Scholar
• Uckun , FM and Mao , C . 2004 . Tyrosine kinases as new molecular targets in treatment of inflammatory disorders and leukemia . Curr. Pharm. Design , 10 : 1083 – 1091 .
   PubMed Web of Science ®Google Scholar
• Kanner , SB and Perez-Villar , JJ . 2003 . Altering T-cell activation by targeting the multidomain tyrosine kinase Itk . Trends Immunol. , 24 : 249 – 253 .
   PubMedGoogle Scholar
• August , A , Fischer , A , Hao , S , Mueller , C and Ragi , M . 2002 . The Tec family of tyrosine kinases in T cells, amplifiers of T cell receptor signals . Int. J. Biochem. Cell B. , 34 : 1184 – 1189 .
   Google Scholar
• Accelrys discovery studio 2.5. Accelrys, San Diego, CA, USA, software available at http://accelrys.com
   Google Scholar
• Das , J , Liu , C , Moquin , RV , Lin , J , Furch , JA , Spergel , SH , McIntyre , KW , Shuster , DJ , O’Day , KD , Penhallow , B , Hung , CY , Kanner , SB , Lin , TA , Dodd , JH , Barrish , JC and Wityak , J . 2006 . Discovery and SAR of 2-amino-5-[(thiomethyl)aryl]thiazoles as potent and selective Itk inhibitors . Bioorg. Med. Chem. Lett. , 16 : 2411 – 2415 .
   PubMed Web of Science ®Google Scholar
• Das , J , Furch , JA , Liu , C , Moquin , RV , Lin , J , Spergel , SH , McIntyre , KW , Shuster , DJ , O’Day , KD , Penhallow , B , Hung , CY , Doweyko , AM , Kamath , A , Zhang , H , Marathe , P , Kanner , SB , Lin , TA , Dodd , JH , Barrish , JC and Wityak , J . 2006 . Discovery and SAR of 2-amino-5-(thioaryl)thiazoles as potent and selective Itk inhibitors . Bioorg. Med. Chem. Lett. , 16 : 3706 – 3712 .
   PubMed Web of Science ®Google Scholar
• Snow , RJ , Abeywardane , A , Campbell , S , Lord , J , Kashem , MA , Khine , HH , King , J , Kowalski , JA , Pullen , SS , Roma , T , Roth , GP , Sarko , CR , Wilson , NS , Winters , MP , Wolak , JP and Cywin , CL . 2007 . Hit-to-lead studies on benzimidazole inhibitors of ITK: Discovery of a novel class of kinase inhibitors . Bioorg. Med. Chem. Lett. , 17 : 3660 – 3665 .
   PubMed Web of Science ®Google Scholar
• Moriarty , KJ , Takahashi , H , Pullen , SS , Khine , HH , Sallati , RH , Raymond , EL , Woska , JR Jr , Jeanfavre , DD , Roth , GP , Winters , MP , Qiao , L , Ryan , D , DesJarlais , R , Robinson , D , Wilson , M , Bobko , M , Cook , BN , Lo , HY , Nemoto , PA , Kashem , MA , Wolak , JP , White , A , Magolda , RL and Tomczuk , B . 2008 . Discovery, SAR and X-ray structure of 1H-benzimidazole-5-carboxylic acid cyclohexyl-methyl-amides as inhibitors of inducible T-cell kinase (Itk) . Bioorg. Med. Chem. Lett. , 18 : 5545 – 5549 .
   PubMed Web of Science ®Google Scholar
• Moriarty , KJ , Winters , M , Qiao , L , Ryan , D , DesJarlis , R , Robinson , D , Cook , BN , Kashem , MA , Kaplita , PV , Liu , LH , Farrell , TM , Khine , HH , King , J , Pullen , SS , Roth , GP , Magolda , R and Takahashi , H . 2008 . Itk kinase inhibitors: Initial efforts to improve the metabolical stability and the cell activity of the benzimidazole lead . Bioorg. Med. Chem. Lett. , 18 : 5537 – 5540 .
   PubMed Web of Science ®Google Scholar
• Winters , MP , Robinson , DJ , Khine , HH , Pullen , SS , Woska , JR Jr , Raymond , EL , Sellati , R , Cywin , CL , Snow , RJ , Kashem , MA , Wolak , JP , King , J , Kaplita , PV , Liu , LH , Farrell , TM , DesJarlais , R , Roth , GP , Takahashi , H and Moriarty , KJ . 2008 . 5-Aminomethyl-1H-benzimidazoles as orally active inhibitors of inducible T-cell kinase (Itk) . Bioorg. Med. Chem. Lett. , 18 : 5541 – 5544 .
   PubMed Web of Science ®Google Scholar
• Cook , BN , Bentzien , J , White , A , Nemoto , PA , Wang , J , Man , CC , Soleymanzadeh , F , Khine , HH , Kashem , MA , Kugler , SZ Jr , Wolak , JP , Roth , GP , Lombaert , SD , Pullen , SS and Takahashi , H . 2009 . Discovery of potent inhibitors of interleukin-2 inducible T-cell kinase (ITK) through structure-based drug design . Bioorg. Med. Chem. Lett. , 19 : 773 – 777 .
   PubMed Web of Science ®Google Scholar
• Lo , HY , Bentzien , J , Fleck , RW , Pullen , SS , Khine , HH , Woska , JR Jr , Kugler , SZ , Kashem , MA and Takahashi , H . 2008 . 2-Aminobenzimidazoles as potent ITK antagonists: Trans-stilbene-like moieties targeting the kinase specificity pocket . Bioorg. Med. Chem. Lett. , 18 : 6218 – 6221 .
   PubMed Web of Science ®Google Scholar
• Riether , D , Zindell , R , Kowalski , JA , Cook , BN , Bentzien , J , Lombaert , SD , Thomson , D , Kugler , SZ Jr , Skow , D , Martin , LS , Raymond , EL , Khine , HH , O’Shea , K , Woska , JR Jr , Jeanfavre , D , Sellati , R , Ralph , KLM , Ahlberg , J , Labissiere , G , Kashem , MA , Pullen , SS and Takahashi , H . 2009 . 5-Aminomethylbenzimdazoles as potent ITK antagonists . Bioorg. Med. Chem. Lett. , 19 : 1588 – 1591 .
   PubMed Web of Science ®Google Scholar
• Lo , HY , Bentzien , J , White , A , Man , CC , Fleck , RW , Pullen , SS , Khine , HH , King , J , Woska , JR Jr , Wolak , JP , Kashem , MA , Roth , GP and Takahashi , H . 2008 . 2-Aminobenzimidazoles as potent ITK antagonists: De novo design of a pyrrole system targeting additional hydrogen bonding interaction . Tetrahedron Lett. , 49 : 7337 – 7340 .
   Web of Science ®Google Scholar
• Chen , CY . 2009 . Pharmacoinformatics approach for mPGES-1 in anti-inflammation by 3D-QSAR pharmacophore mapping . J. Taiwan Inst. Chem. Eng. , 40 : 155 – 161 .
   Web of Science ®Google Scholar
• Smellie , A , Teig , S and Towbin , P . 1995 . Poling: Promoting conformational coverage . J. Comput. Chem. , 16 : 171 – 187 .
   Web of Science ®Google Scholar
• Güner , OF . 2000 . Pharmacophore Perception, Development, and Use in Drug Design , 173 – 188 . La Jolla, California : International University Line .
   Google Scholar
• Debnath , AK . 2002 . Pharmacophore mapping of a series of 2,4-diamino-5-deazapteridine inhibitors of mycobacterium avium complex dihydrofolate reductase . J. Med. Chem. , 45 : 41 – 53 .
   PubMed Web of Science ®Google Scholar
• Macdougall , IJ and Griffith , R . 2008 . Pharmacophore design and database searching for selective monoamine neurotransmitter transporter ligands . J. Mol. Graph. Model. , 26 : 1113 – 1124 .
   PubMed Web of Science ®Google Scholar
• Bharatham , N , Bharatham , K and Lee , KW . 2007 . Pharmacophore identification and virtual screening for methionyl-tRNA synthetase inhibitors . J. Mol. Graph. Model. , 25 : 813 – 823 .
   PubMed Web of Science ®Google Scholar
• Brown , K , Long , JM , Vial , SC , Dedi , N , Dunster , NJ , Renwick , SB , Tanner , AJ , Frantz , JD , Fleming , MA and Cheetham. , GM . 2004 . Crystal structures of interleukin-2 tyrosine kinase and their implications for the design of selective inhibitor . J. Biol. Chem. , 279 : 18727 – 18732 .
   PubMed Web of Science ®Google Scholar
• Li , HF , Lu , T , Zhu , T , Jiang , YJ , Rao , SS , Hu , LY , Xin , BT and Chen , YD . 2009 . Virtual screening for Raf-1 kinase inhibitors based on pharmacophore model of substituted ureas . Eur. J. Med. Chem. , 44 : 1240 – 1249 .
   PubMed Web of Science ®Google Scholar