메뉴 건너뛰기




Volumn 46, Issue 14, 2003, Pages 2917-2931

Development of natural product-derived receptor tyrosine kinase inhibitors based on conservation of protein domain fold

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOPOIETIN RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR; NAKIJIQUINONE C; NAKIJIQUINONE D; NATURAL PRODUCT; PROTEIN TYROSINE KINASE INHIBITOR; SOMATOMEDIN C RECEPTOR; UNCLASSIFIED DRUG; VASCULOTROPIN RECEPTOR 1; VASCULOTROPIN RECEPTOR 2; VASCULOTROPIN RECEPTOR 3;

EID: 0038798615     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0307943     Document Type: Article
Times cited : (77)

References (52)
  • 1
    • 0033786922 scopus 로고    scopus 로고
    • Protein tyrosine kinases: Structure and function
    • Hubbard, S. R.; Till, J. H. Protein Tyrosine Kinases: Structure and Function. Annu. Rev. Biochem. 2000, 69, 373-98.
    • (2000) Annu. Rev. Biochem. , vol.69 , pp. 373-398
    • Hubbard, S.R.1    Till, J.H.2
  • 3
    • 0035114105 scopus 로고    scopus 로고
    • Involvement of Flt-1 tyrosine kinase (vascular endothelial growth factor receptor-1) in pathological angiogenesis
    • Hiratsuka, S.; Maru, Y.; Okada, A.; Seiki, M.; Noda, T.; Shibuya, M. Involvement of Flt-1 tyrosine kinase (vascular endothelial growth factor receptor-1) in pathological angiogenesis. Cancer Res. 2001, 61, 1207-1213.
    • (2001) Cancer Res. , vol.61 , pp. 1207-1213
    • Hiratsuka, S.1    Maru, Y.2    Okada, A.3    Seiki, M.4    Noda, T.5    Shibuya, M.6
  • 5
    • 0035255001 scopus 로고    scopus 로고
    • Differential inhibition of tumor angiogenesis by TIE2 and vascular endothelial growth factor receptor-2 dominant-negative receptor mutants
    • Stratmann, A.; Acker, T.; Burger, A. M.; Amann, K.; Risau, W.; Plate, K. H. Differential inhibition of tumor angiogenesis by TIE2 and vascular endothelial growth factor receptor-2 dominant-negative receptor mutants. Int. J. Cancer 2001, 91, 273-282.
    • (2001) Int. J. Cancer , vol.91 , pp. 273-282
    • Stratmann, A.1    Acker, T.2    Burger, A.M.3    Amann, K.4    Risau, W.5    Plate, K.H.6
  • 8
    • 0000945738 scopus 로고    scopus 로고
    • Integrin antagonists and other low molecular weight compounds as inhibitors of angiogenesis: New drugs in cancer therapy
    • Giannis, A.; Rübsam, F. Integrin antagonists and other low molecular weight compounds as inhibitors of angiogenesis: New drugs in cancer therapy. Angew. Chem. 1997, 109, 606-609; Angew. Chem., Int. Ed. Engl. 1997, 36, 588-590 and refs therein.
    • (1997) Angew. Chem. , vol.109 , pp. 606-609
    • Giannis, A.1    Rübsam, F.2
  • 9
    • 0030893498 scopus 로고    scopus 로고
    • and refs therein
    • Giannis, A.; Rübsam, F. Integrin antagonists and other low molecular weight compounds as inhibitors of angiogenesis: New drugs in cancer therapy. Angew. Chem. 1997, 109, 606-609; Angew. Chem., Int. Ed. Engl. 1997, 36, 588-590 and refs therein.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 588-590
  • 10
    • 0034648765 scopus 로고    scopus 로고
    • Angiogenesis in cancer and other diseases
    • and refs therein
    • Carmeliet, P.; Jain, R. K. Angiogenesis in cancer and other diseases. Nature 2000, 407, 249-257 and refs therein.
    • (2000) Nature , vol.407 , pp. 249-257
    • Carmeliet, P.1    Jain, R.K.2
  • 11
    • 0033961671 scopus 로고    scopus 로고
    • Regulation of survival signals from the insulin-like growth factor-I receptor
    • O'Connor, R.; Fennely, C.; Krause, D. Regulation of survival signals from the insulin-like growth factor-I receptor. Biochem. Soc. Trans. 2000, 28, 47-51.
    • (2000) Biochem. Soc. Trans. , vol.28 , pp. 47-51
    • O'Connor, R.1    Fennely, C.2    Krause, D.3
  • 12
    • 0026354476 scopus 로고
    • Cell transformation potential of a HER2 transmembrane domain deletion mutant retained in the endoplasmic reticulum
    • Hudziak, R. M.; Ullrich, A. Cell transformation potential of a HER2 transmembrane domain deletion mutant retained in the endoplasmic reticulum. J. Biol. Chem. 1991, 266, 24109-14115.
    • (1991) J. Biol. Chem. , vol.266 , pp. 24109-14115
    • Hudziak, R.M.1    Ullrich, A.2
  • 13
    • 0002608471 scopus 로고    scopus 로고
    • Growth factor receptor in cell transformation
    • Peters, G., Vousden, K., Eds.; Oxford University Press, Cary, NC
    • Heldin, C.-H.; Rönnstrand, L. Growth factor receptor in cell transformation. In Oncogenes and Tumor Suppressors; Peters, G., Vousden, K., Eds.; Oxford University Press, Cary, NC, 1997; pp 55-85.
    • (1997) Oncogenes and Tumor Suppressors , pp. 55-85
    • Heldin, C.-H.1    Rönnstrand, L.2
  • 14
    • 0036527429 scopus 로고    scopus 로고
    • Protein kinases - The major drug targets of the twenty-first century?
    • Cohen, P. Protein kinases- the major drug targets of the twenty-first century? Nat. Rev. Cancer 2002, 1, 309-315.
    • (2002) Nat. Rev. Cancer , vol.1 , pp. 309-315
    • Cohen, P.1
  • 15
    • 0035413617 scopus 로고    scopus 로고
    • Chemical inhibitors of protein kinases
    • Bridges, A. J. Chemical Inhibitors of Protein Kinases. Chem. Rev. 2001, 101, 2541-2571.
    • (2001) Chem. Rev. , vol.101 , pp. 2541-2571
    • Bridges, A.J.1
  • 16
    • 0037119336 scopus 로고    scopus 로고
    • From protein domains to drug candidates - Natural products as guiding principles in the design and synthesis of compound libraries
    • Breinbauer, R.; Vetter, I.; Waldmann, H. From Protein Domains to Drug Candidates - Natural Products as Guiding Principles in the Design and Synthesis of Compound Libraries. Angew. Chem., Int. Ed. 2002, 41, 2878-2890.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2878-2890
    • Breinbauer, R.1    Vetter, I.2    Waldmann, H.3
  • 17
    • 0037006785 scopus 로고    scopus 로고
    • Natural product derived receptor tyrosine kinase inhibitors: Identification of IGF1R, Tie-2 and VEGFR-3 inhibitors
    • Part of this work was published in preliminary form: Stahl, P.; Kissau, L.; Mazitschek, R.; Giannis, A.; Waldmann, H. Natural Product Derived Receptor Tyrosine Kinase Inhibitors: Identification of IGF1R, Tie-2 and VEGFR-3 Inhibitors. Angew. Chem., Int. Ed. 2002, 41,1174-1178.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1174-1178
    • Stahl, P.1    Kissau, L.2    Mazitschek, R.3    Giannis, A.4    Waldmann, H.5
  • 18
    • 0029142486 scopus 로고
    • Nakijiquinones C and D, new sesquiterpenoid quinones with a hydroxy amino acid residue from a marine sponge inhibiting c-erbB-2 kinase
    • Kobayashi, J.; Madono, T.; Shigemori, H. Nakijiquinones C and D, New Sesquiterpenoid Quinones with a Hydroxy Amino Acid Residue from a Marine Sponge Inhibiting c-erbB-2 Kinase. Tetrahedron 1995, 51, 10867-10874.
    • (1995) Tetrahedron , vol.51 , pp. 10867-10874
    • Kobayashi, J.1    Madono, T.2    Shigemori, H.3
  • 21
    • 0027194711 scopus 로고
    • Synthetic approaches toward spiro[2,3-dihydro-4H-1-benzopyran-4,1′-cyclohexan]-2-one derivatives via radical reactions: Total synthesis of (±)-lycoramine. O
    • Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T. Hoshino, Synthetic approaches toward spiro[2,3-dihydro-4H-1-benzopyran-4,1′-cyclohexan]-2-one derivatives via radical reactions: total synthesis of (±)-lycoramine. O. J. Org. Chem. 1993, 58, 3877-3885.
    • (1993) J. Org. Chem. , vol.58 , pp. 3877-3885
    • Ishizaki, M.1    Ozaki, K.2    Kanematsu, A.3    Isoda, T.4    Hoshino5
  • 22
    • 0000711831 scopus 로고
    • A convenient synthesis of juglone via neutral salcomine oxidation
    • Wakamatsu, T.; Nishi, T.; Ohnuma, T.; Ban, Y. A convenient synthesis of juglone via neutral salcomine oxidation. Synth. Commun. 1984, 14, 1167-1173.
    • (1984) Synth. Commun. , vol.14 , pp. 1167-1173
    • Wakamatsu, T.1    Nishi, T.2    Ohnuma, T.3    Ban, Y.4
  • 23
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross-coupling reactions of organoboron compounds
    • Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457-2483.
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 24
    • 37049105775 scopus 로고
    • A new method for the deoxygenation of tertiary and secondary alcohols
    • Dolan, S. C.; Millan, J. M. A New Method for the Deoxygenation of Tertiary and Secondary Alcohols. J. Chem. Soc., Chem. Commun. 1985, 22, 1588-1589.
    • (1985) J. Chem. Soc., Chem. Commun. , vol.22 , pp. 1588-1589
    • Dolan, S.C.1    Millan, J.M.2
  • 25
    • 0013231355 scopus 로고
    • Anthracyclinone. 3. Chiral pool synthesis of anthracyclinones via tetralin intermediates
    • Genot, A.; Florent, J.-C.; Monneret, C. Anthracyclinone. 3. Chiral pool synthesis of anthracyclinones via tetralin intermediates. J. Org. Chem. 1987, 52, 1057-1063.
    • (1987) J. Org. Chem. , vol.52 , pp. 1057-1063
    • Genot, A.1    Florent, J.-C.2    Monneret, C.3
  • 26
    • 33845373603 scopus 로고
    • Simple and selective method for aldehydes (RCHO) fwdarw. (E)-haloalkenes (RCH: CHX) conversion by means of a haloform-chromous chloride system
    • Takai, K.; Nitta, K.; Utimoto, K. Simple and selective method for aldehydes (RCHO) fwdarw. (E)-haloalkenes (RCH: CHX) conversion by means of a haloform-chromous chloride system. J. Am. Chem. Soc. 1986, 108, 7408-7410.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7408-7410
    • Takai, K.1    Nitta, K.2    Utimoto, K.3
  • 27
    • 0028290720 scopus 로고
    • Stereochemistry in carbenoid formation by bromine/lithium and bromine/zinc exchange reactions of gem-dibromo compounds
    • Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. Stereochemistry in carbenoid formation by bromine/lithium and bromine/zinc exchange reactions of gem-dibromo compounds. Tetrahedron 1994, 50, 7987-8002.
    • (1994) Tetrahedron , vol.50 , pp. 7987-8002
    • Harada, T.1    Katsuhira, T.2    Hattori, K.3    Oku, A.4
  • 28
    • 0028900262 scopus 로고
    • Synthesis and mass spectral data of four potential biomarkers related to the C19 tricyclanes found Australian oils and puget sound sediments
    • Kaufman, T. S. Synthesis and mass spectral data of four potential biomarkers related to the C19 tricyclanes found Australian oils and puget sound sediments. Synth. Commun. 1995, 25, 1205-1221.
    • (1995) Synth. Commun. , vol.25 , pp. 1205-1221
    • Kaufman, T.S.1
  • 29
    • 0037598934 scopus 로고    scopus 로고
    • See ref 1 and refs cited therein
    • See ref 1 and refs cited therein.
  • 31
    • 0038274218 scopus 로고    scopus 로고
    • note
    • A homology model of the ATP binding site of KDR has been used to evaluate the anilinophthalazine-class of RTK Inhibitors. See ref 18.
  • 32
    • 0038274217 scopus 로고    scopus 로고
    • note
    • PDB entries 1FGI and 2FGI
  • 34
    • 0038274221 scopus 로고    scopus 로고
    • note
    • This assumption would have also permitted the choice of the IGF1R or IRK structure as a templates. Indeed, this possibility was exploited, and the resulting 3D models were also used in the evaluation of the nakijiquinone analogues. However, the sequence homology to the VEGFs and Tie-2 is lower.
  • 35
    • 0033559918 scopus 로고    scopus 로고
    • Hydrogen bonding, hydrophobic interactions, and failure of the rigid receptor hypothesis
    • Davis, A. M.; Teague, S. J. Hydrogen Bonding, Hydrophobic Interactions, and Failure of the Rigid Receptor Hypothesis. Angew. Chem., Int. Ed. 1999, 38, 736-749.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 736-749
    • Davis, A.M.1    Teague, S.J.2
  • 36
    • 0030945871 scopus 로고    scopus 로고
    • Structure of the tyrosine kinase domain of fibroblast growth receptor in complex with inhibitors
    • Mohammadi, M.; McMahon, G.; Sun, L.; Tang, C.; Hirth, P.; Yeh, B. K.; Hubbard, S. R.; Schlessinger, J. Structure of the Tyrosine Kinase Domain of Fibroblast Growth Receptor in Complex with Inhibitors. Science 1997, 276, 955-960.
    • (1997) Science , vol.276 , pp. 955-960
    • Mohammadi, M.1    McMahon, G.2    Sun, L.3    Tang, C.4    Hirth, P.5    Yeh, B.K.6    Hubbard, S.R.7    Schlessinger, J.8
  • 37
    • 0032945593 scopus 로고    scopus 로고
    • Improvement of the segment-to-segment approach to multiple sequence alignment
    • Morgenstern, B. Improvement of the segment-to-segment approach to multiple sequence alignment. Bioinformatics 1999, 15, 211-218.
    • (1999) Bioinformatics , vol.15 , pp. 211-218
    • Morgenstern, B.1
  • 39
    • 0037598933 scopus 로고    scopus 로고
    • For additional references and information please refer to Sali@rockvax.rockefeller.edu
    • Modeller 4.0 Manual. For additional references and information please refer to Sali@rockvax.rockefeller.edu.
    • Modeller 4.0 Manual
  • 41
    • 0038274220 scopus 로고    scopus 로고
    • note
    • WitnotP is a molecular modeling software developed by and licensed from Novartis AG, Basel, Switzerland. For further information and licensing conditions please contact Dr. Armin Widmer at Novartis AG.
  • 43
    • 0038613152 scopus 로고    scopus 로고
    • note
    • For a detailed description of how this figure was created, see Experimental Section.
  • 44
    • 0026342401 scopus 로고
    • Crystal structure of the catalytic subunit of cyclic adenosine monophosphate-dependent protein kinase
    • Knighton, D. R.; Zheng, J. H.; Ten Eyck, L. F.; Ashford, V. A.; Xuong, N. H.; Taylor; S. S.; Sowadski, J. M. Crystal Structure of the Catalytic Subunit of Cyclic Adenosine Monophosphate-Dependent Protein Kinase. Science 1991, 253, 407-414.
    • (1991) Science , vol.253 , pp. 407-414
    • Knighton, D.R.1    Zheng, J.H.2    Ten Eyck, L.F.3    Ashford, V.A.4    Xuong, N.H.5    Taylor, S.S.6    Sowadski, J.M.7
  • 47
    • 0037124205 scopus 로고    scopus 로고
    • Pyrrolo[2,3-d]pyrimidines containing diverse N-7 substituents as potent inhibitors of Lck
    • Calderwood, D. J.; Johnston, D. N.; Munschauer, R.; Rafferty, P. Pyrrolo[2,3-d]pyrimidines Containing Diverse N-7 Substituents as Potent Inhibitors of Lck. Bioorg. Med. Chem. Lett. 2002, 12, 1683-1686.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1683-1686
    • Calderwood, D.J.1    Johnston, D.N.2    Munschauer, R.3    Rafferty, P.4
  • 49
    • 0038480375 scopus 로고    scopus 로고
    • Traceless solid-phase synthesis of 2-aminothiazoles: Receptor tyrosine kinase inhibitors with dual selectivity for Tie-2 and VEGFR-2
    • Stieber, F.; Mazitschek, R.; Soric, N.; Giannis, A.; Waldmann, H. Traceless Solid-Phase Synthesis of 2-Aminothiazoles: Receptor Tyrosine Kinase Inhibitors with Dual Selectivity for Tie-2 and VEGFR-2. Angew. Chem., Int. Ed. 2002, 41, 4757-4761.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 4757-4761
    • Stieber, F.1    Mazitschek, R.2    Soric, N.3    Giannis, A.4    Waldmann, H.5
  • 51
    • 0038613151 scopus 로고    scopus 로고
    • note
    • A homology model of the IGF1R kinase domain was also created. The conclusions drawn with respect to the binding modes of the nakijiquinone analogues were essentially the same as those derived from the available crystal structures.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.