메뉴 건너뛰기




Volumn 48, Issue 11, 2005, Pages 3776-3783

Synthesis, modeling, and in vitro activity of (3′S)-epi-K-252a analogues. Elucidating the stereochemical requirements of the 3′-sugar alcohol on trkA tyrosine kinase activity

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE; GLUTAMIC ACID; K 252A; PROTEIN TYROSINE KINASE A; SUGAR ALCOHOL;

EID: 20144381281     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040178m     Document Type: Article
Times cited : (22)

References (52)
  • 1
    • 0027177678 scopus 로고
    • The neurotrophins and their receptors
    • (a) Glass, D. J.; Yancopoulos, G. D. The neurotrophins and their receptors. Trends Cell Biol. 1993, 3, 262-268.
    • (1993) Trends Cell Biol. , vol.3 , pp. 262-268
    • Glass, D.J.1    Yancopoulos, G.D.2
  • 2
    • 0026766860 scopus 로고
    • The nerve growth factor family of receptors
    • (b) Meakin, S. O.; Shooter, E. M. The nerve growth factor family of receptors. Trends Neurosci. 1992, 15, 323-331.
    • (1992) Trends Neurosci. , vol.15 , pp. 323-331
    • Meakin, S.O.1    Shooter, E.M.2
  • 4
    • 0026212441 scopus 로고
    • Identification of tyrosine kinase Trk as a nerve growth factor receptor
    • (d) Ross, A. H. Identification of tyrosine kinase Trk as a nerve growth factor receptor. Cell Regul. 1991, 2, 685-690.
    • (1991) Cell Regul. , vol.2 , pp. 685-690
    • Ross, A.H.1
  • 5
    • 0025343230 scopus 로고
    • Signal transduction by receptor with tyrosine kinase activity
    • (e) Ullrich, A.; Schlessinger, J. Signal transduction by receptor with tyrosine kinase activity. Cell 1990, 61, 203-212.
    • (1990) Cell , vol.61 , pp. 203-212
    • Ullrich, A.1    Schlessinger, J.2
  • 6
    • 0025735392 scopus 로고
    • The trk proto-oncogene product: A signal transducing receptor for nerve growth factor
    • (f) Kaplan, D. R.; Hempstead, B. L.; Martin-Zanca, D.; Chao, M. V.; Parada, L. F. The trk proto-oncogene product: a signal transducing receptor for nerve growth factor. Science 1991, 252, 554-558.
    • (1991) Science , vol.252 , pp. 554-558
    • Kaplan, D.R.1    Hempstead, B.L.2    Martin-Zanca, D.3    Chao, M.V.4    Parada, L.F.5
  • 7
    • 0028115022 scopus 로고
    • Neurotrophin signal transduction by the Trk receptor
    • Kaplan, D. R.; Stephens, M. R. Neurotrophin signal transduction by the Trk receptor. J. Neurobiol. 1994, 25, 1404-1417.
    • (1994) J. Neurobiol. , vol.25 , pp. 1404-1417
    • Kaplan, D.R.1    Stephens, M.R.2
  • 8
    • 0019071287 scopus 로고
    • Physiology of nerve growth factor
    • (a) Thoenen, H.; Barde, Y. A. Physiology of nerve growth factor. Physiol. Rev. 1980, 60, 1284-1335.
    • (1980) Physiol. Rev. , vol.60 , pp. 1284-1335
    • Thoenen, H.1    Barde, Y.A.2
  • 9
    • 0342288702 scopus 로고
    • Pharmacology of neurotrophic factors in models of neurodegenerative diseases
    • (b) DiStefano, P. S. Pharmacology of neurotrophic factors in models of neurodegenerative diseases. Annu. Rep. Med. Chem. 1993, 28, 11-17.
    • (1993) Annu. Rep. Med. Chem. , vol.28 , pp. 11-17
    • DiStefano, P.S.1
  • 10
    • 0642316039 scopus 로고    scopus 로고
    • Nerve growth factor: Structure, function and therapeutic implications for Alzheimer's disease
    • (c) Lad, S. P.; Neet, K. E.; Mufson, E. J. Nerve growth factor: structure, function and therapeutic implications for Alzheimer's disease. Current Drug Targets- CNS and Neurological Disorders 2003, 2, 315-334.
    • (2003) Current Drug Targets- CNS and Neurological Disorders , vol.2 , pp. 315-334
    • Lad, S.P.1    Neet, K.E.2    Mufson, E.J.3
  • 11
    • 0032877546 scopus 로고    scopus 로고
    • Role of Neurotrophin-Trk interactions in oncology: The antitumor efficacy of potent and selective trk tyrosine kinase inhibitors in pre-clinical tumor models
    • (a) Ruggeri, B. A.; Miknyoczki, S. J.; Singh, J.; Hudkins, R. L. Role of Neurotrophin-Trk interactions in oncology: the antitumor efficacy of potent and selective trk tyrosine kinase inhibitors in pre-clinical tumor models. Curr. Med. Chem. 1999, 6, 845-857.
    • (1999) Curr. Med. Chem. , vol.6 , pp. 845-857
    • Ruggeri, B.A.1    Miknyoczki, S.J.2    Singh, J.3    Hudkins, R.L.4
  • 12
    • 0030429531 scopus 로고    scopus 로고
    • Neurotrophin-trk receptor interactions in neoplasia: A possible role in interstitial and perineural invasion in ductal pancreatic cancer
    • (b) Miknyoczki, S. J.; Klein-Szanto, A. J. P.; Ruggeri, B. A. Neurotrophin-trk receptor interactions in neoplasia: a possible role in interstitial and perineural invasion in ductal pancreatic cancer. Crit. Rev. Oncog. 1996, 7, 89-100.
    • (1996) Crit. Rev. Oncog. , vol.7 , pp. 89-100
    • Miknyoczki, S.J.1    Klein-Szanto, A.J.P.2    Ruggeri, B.A.3
  • 13
    • 0032939723 scopus 로고    scopus 로고
    • Neurotrophins and trk receptors in human pancreatic ductal adrenocarcinoma: Expression patterns and effects on in vitro invasive behavior
    • (c) Miknyoczki, S. J.; Lang, L.; Klein-Szanto, A. J. P.; Dionne, C. A.; Ruggeri, B. A. Neurotrophins and trk receptors in human pancreatic ductal adrenocarcinoma: Expression patterns and effects on in vitro invasive behavior. Int. J. Cancer 1999, 81, 417-427.
    • (1999) Int. J. Cancer , vol.81 , pp. 417-427
    • Miknyoczki, S.J.1    Lang, L.2    Klein-Szanto, A.J.P.3    Dionne, C.A.4    Ruggeri, B.A.5
  • 14
    • 0036284490 scopus 로고    scopus 로고
    • The neurotrophin-trk receptor axes are critical for the growth and progression of human prostatic carcinoma and pancreatic ductal adenocarcinoma xenographs in nude mice
    • (d) Miknyoczki, S. J.; Wan, W.; Chang, H.; Dobrzanski, P.; Ruggeri, B. A.; Dionne, C. A.; Buchkovich, K. The neurotrophin-trk receptor axes are critical for the growth and progression of human prostatic carcinoma and pancreatic ductal adenocarcinoma xenographs in nude mice. Clin. Cancer Res. 2002, 8, 1924-1931.
    • (2002) Clin. Cancer Res. , vol.8 , pp. 1924-1931
    • Miknyoczki, S.J.1    Wan, W.2    Chang, H.3    Dobrzanski, P.4    Ruggeri, B.A.5    Dionne, C.A.6    Buchkovich, K.7
  • 15
    • 0028851242 scopus 로고
    • Expression of a high affinity nerve growth factor receptor in the human prostate
    • (e) Pflug, B. R.; Dionne, C.; Kaplan, D. R.; Lynch, J.; Djakiew, D. Expression of a high affinity nerve growth factor receptor in the human prostate. Endocrinology 1995, 136, 262-268.
    • (1995) Endocrinology , vol.136 , pp. 262-268
    • Pflug, B.R.1    Dionne, C.2    Kaplan, D.R.3    Lynch, J.4    Djakiew, D.5
  • 17
    • 0025895786 scopus 로고
    • Regulation of growth by a nerve growth factor-like protein which modulates paracrine interactions between a neoplastic epithelial cell line and stromal cells of the human prostate
    • (a) Djakiew, D.; Delsite, R.; Pflug, B.; Wrathall, J.; Lynch, J. H.; Onoda, M. Regulation of growth by a nerve growth factor-like protein which modulates paracrine interactions between a neoplastic epithelial cell line and stromal cells of the human prostate. Cancer Res. 1991, 51, 3304.
    • (1991) Cancer Res. , vol.51 , pp. 3304
    • Djakiew, D.1    Delsite, R.2    Pflug, B.3    Wrathall, J.4    Lynch, J.H.5    Onoda, M.6
  • 18
    • 0034881357 scopus 로고    scopus 로고
    • Pan-trk inhibition decreases metastasis and enhances host survival in experimental models due to its selective induction of apoptosis of prostate cancer cell
    • (b) Weeraratna, A. T.; Dalrymple, S. L.; Lamb, J. C.; Denmeade, S. R.; Miknyoczki, S.; Dionne, C. A.; Isaacs, J. T. Pan-trk inhibition decreases metastasis and enhances host survival in experimental models due to its selective induction of apoptosis of prostate cancer cell. Clin. Cancer Res. 2001, 7, 2237-2245.
    • (2001) Clin. Cancer Res. , vol.7 , pp. 2237-2245
    • Weeraratna, A.T.1    Dalrymple, S.L.2    Lamb, J.C.3    Denmeade, S.R.4    Miknyoczki, S.5    Dionne, C.A.6    Isaacs, J.T.7
  • 20
    • 0034881357 scopus 로고    scopus 로고
    • Pan-trk inhibition decreases metastasis and enhances host survival in experimental models due to its selective induction of apoptosis of prostate cancer cell
    • (d) Weeraratna, A. T.; Dalrymple, S. L.; Lamb, J. C.; Denmeade, S. R.; Miknyoczki, S.; Dionne, C. A.; Isaacs, J. T. Pan-trk inhibition decreases metastasis and enhances host survival in experimental models due to its selective induction of apoptosis of prostate cancer cell. Clin. Cancer Res. 2001, 7, 2237-2245.
    • (2001) Clin. Cancer Res. , vol.7 , pp. 2237-2245
    • Weeraratna, A.T.1    Dalrymple, S.L.2    Lamb, J.C.3    Denmeade, S.R.4    Miknyoczki, S.5    Dionne, C.A.6    Isaacs, J.T.7
  • 22
    • 0022500301 scopus 로고
    • K-252a, a potent inhibitor of protein kinase C from microbial origin
    • (b) Kase, H.; Iwahashi, K; Matsuda, Y. K-252a, a potent inhibitor of protein kinase C from microbial origin. J. Antibiot. 1986, 39, 1059-1065.
    • (1986) J. Antibiot. , vol.39 , pp. 1059-1065
    • Kase, H.1    Iwahashi, K.2    Matsuda, Y.3
  • 24
    • 0032518196 scopus 로고    scopus 로고
    • Kinetics of trkA tyrosine kinase activity and inhibition by K-252a
    • Angeles, T. S.; Yang, S. X.; Steffler, C.; Dionne, C. A.; Kinetics of trkA tyrosine kinase activity and inhibition by K-252a. Arch. Biochem. Biophys. 1998, 349, 267-274.
    • (1998) Arch. Biochem. Biophys. , vol.349 , pp. 267-274
    • Angeles, T.S.1    Yang, S.X.2    Steffler, C.3    Dionne, C.A.4
  • 26
    • 0026512998 scopus 로고
    • K-252a inhibits nerve growth factor-induced trk proto-oncogene tyrosine phosphorylation and kinase activity
    • (a) Berg, M. M.; Sternberg, D. W.; Parada, L. F.; Chao, M. V. K-252a inhibits nerve growth factor-induced trk proto-oncogene tyrosine phosphorylation and kinase activity. J. Biol. Chem. 1992, 267, 13-16.
    • (1992) J. Biol. Chem. , vol.267 , pp. 13-16
    • Berg, M.M.1    Sternberg, D.W.2    Parada, L.F.3    Chao, M.V.4
  • 27
    • 0026563244 scopus 로고
    • K-252a is a selective inhibitor of the tyrosine protein kinase activity of the trk family of oncogenes and neurotrophin receptors
    • (b) Tarpley, P. Lamballe, F., Barbacid, M. K-252a is a selective inhibitor of the tyrosine protein kinase activity of the trk family of oncogenes and neurotrophin receptors. Oncogene 1992, 7, 371-381.
    • (1992) Oncogene , vol.7 , pp. 371-381
    • Tarpley, P.1    Lamballe, F.2    Barbacid, M.3
  • 28
    • 0026684676 scopus 로고
    • Inhibition of the cellular actions of nerve growth factor by staurosporine and K-252a results from the attenuation of the activity of the trk tyrosine kinase
    • (c) Ohmichi, M.; Decker, S. J.; Pang, I.; Saltiel, A. R. Inhibition of the cellular actions of nerve growth factor by staurosporine and K-252a results from the attenuation of the activity of the trk tyrosine kinase. Biochemistry 1992, 31, 4034-4039.
    • (1992) Biochemistry , vol.31 , pp. 4034-4039
    • Ohmichi, M.1    Decker, S.J.2    Pang, I.3    Saltiel, A.R.4
  • 29
    • 0026648471 scopus 로고
    • Specific inhibition of NGF receptor tyrosine kinase activity by K-252a
    • (d) Muroya, K; Hashimoto, Y.; Hattori, S.; Nakamuru, S. Specific inhibition of NGF receptor tyrosine kinase activity by K-252a. Biochim. Biophys. Acta 1992, 1135, 353-356.
    • (1992) Biochim. Biophys. Acta , vol.1135 , pp. 353-356
    • Muroya, K.1    Hashimoto, Y.2    Hattori, S.3    Nakamuru, S.4
  • 31
    • 0026595294 scopus 로고
    • K-252 compounds: Modulators of neurotrophin signal transduction
    • Knusel, B.; Hefti, H. K-252 compounds: modulators of neurotrophin signal transduction. J. Neurochem. 1992, 59, 1987-1995.
    • (1992) J. Neurochem. , vol.59 , pp. 1987-1995
    • Knusel, B.1    Hefti, H.2
  • 35
    • 0032771840 scopus 로고
    • The Trk tyrosine kinase inhibitor CEP-701 (KT-5555) exhibits significant antitumor efficacy in preclinical xenograft models of human pancreatic ductal adenocarcinoma
    • Miknyoczki, S. J.; Chang, H.; Klein-Szanto, A.; Dionne, C. A.; Ruggeri, B. A. The Trk tyrosine kinase inhibitor CEP-701 (KT-5555) exhibits significant antitumor efficacy in preclinical xenograft models of human pancreatic ductal adenocarcinoma. Clin. Cancer Res. 1945, 5, 2205-2212.
    • (1945) Clin. Cancer Res. , vol.5 , pp. 2205-2212
    • Miknyoczki, S.J.1    Chang, H.2    Klein-Szanto, A.3    Dionne, C.A.4    Ruggeri, B.A.5
  • 36
    • 0033563119 scopus 로고    scopus 로고
    • Sustained in vivo regression of Dunning H rat prostate cancers treated with combinations of androgen ablation and trk tyrosine kinase inhibitors, CEP-751 (KT-6587) or CEP-701 (KT-5555)
    • George, D. J.; Dionne, C. A.; Jani, J.; Angeles, T.; Murakata, D.; Lamb, J.; Isaacs, J. T. Sustained in vivo regression of Dunning H rat prostate cancers treated with combinations of androgen ablation and trk tyrosine kinase inhibitors, CEP-751 (KT-6587) or CEP-701 (KT-5555). Cancer Res. 1999, 59, 2395-2401.
    • (1999) Cancer Res. , vol.59 , pp. 2395-2401
    • George, D.J.1    Dionne, C.A.2    Jani, J.3    Angeles, T.4    Murakata, D.5    Lamb, J.6    Isaacs, J.T.7
  • 39
    • 20144378708 scopus 로고    scopus 로고
    • Use of indolocarbazole derivatives to treat a pathological condition of the prostate. US 5516771
    • (c) Dionne, C. A.; Contreras, P. C.; Murakata, C. Use of indolocarbazole derivatives to treat a pathological condition of the prostate. US 5516771.
    • Dionne, C.A.1    Contreras, P.C.2    Murakata, C.3
  • 40
    • 0037152506 scopus 로고    scopus 로고
    • Synthesis and kinase inhibitory activity of 3′-(S)-epi-K-252a
    • Gingrich, D. E.; Hudkins, R. L. Synthesis and kinase inhibitory activity of 3′-(S)-epi-K-252a. Bioorg. Med. Chem. Lett. 2002, 12, 2829-2831.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 2829-2831
    • Gingrich, D.E.1    Hudkins, R.L.2
  • 41
    • 20144380907 scopus 로고    scopus 로고
    • 3′-epimeric K-252 derivatives. US 6093713
    • (a) Hudkins, R. L.; Gingrich, D. 3′-Epimeric K-252 derivatives. US 6093713.
    • Hudkins, R.L.1    Gingrich, D.2
  • 42
    • 20144386462 scopus 로고    scopus 로고
    • 3′-Epimeric K-252 derivatives for treating neurological disorders and cancer. US 6451786
    • (b) Hudkins, R. L.; Gingrich, D. 3′-Epimeric K-252 derivatives for treating neurological disorders and cancer. US 6451786.
    • Hudkins, R.L.1    Gingrich, D.2
  • 44
    • 33947483562 scopus 로고
    • A new stereospecific olefin synthesis from 1,3-diols
    • Corey, E. J.; Winter, R. A. E. A new stereospecific olefin synthesis from 1,3-diols. J. Am. Chem. Soc. 1963, 85, 2677-2680.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2677-2680
    • Corey, E.J.1    Winter, R.A.E.2
  • 45
    • 0032847677 scopus 로고    scopus 로고
    • Protein kinase C in the treatment of disease: Signal transduction pathways, inhibitors, and agents in development
    • Goekjian, P. G.; Jirousek, M. R. Protein kinase C in the treatment of disease: signal transduction pathways, inhibitors, and agents in development. Curr. Med. Chem. 1999, 6, 877-903.
    • (1999) Curr. Med. Chem. , vol.6 , pp. 877-903
    • Goekjian, P.G.1    Jirousek, M.R.2
  • 47
    • 0028870428 scopus 로고
    • K-252a induces tyrosine phosphorylation of the focal adhesion kinase and neurite outgrowth in human neuroblastoma SH-SY5Y cells
    • (b) Maroney, A. C.; Lipfert, L.; Forbes, M. E.; Glicksman, M. A.; Neff, N. T.; Siman, R.; Dionne, C. A. K-252a induces tyrosine phosphorylation of the focal adhesion kinase and neurite outgrowth in human neuroblastoma SH-SY5Y cells. J. Neurochem. 1995, 64, 540-549.
    • (1995) J. Neurochem. , vol.64 , pp. 540-549
    • Maroney, A.C.1    Lipfert, L.2    Forbes, M.E.3    Glicksman, M.A.4    Neff, N.T.5    Siman, R.6    Dionne, C.A.7
  • 48
    • 0242268455 scopus 로고    scopus 로고
    • Crystal structure of the tyrosine kinase domain of the hepatocyte growth factor receptor c-met and its complex with the microbial alkaloid K-252a
    • Schierling, N.; Knapp, S.; Marconi, M.; Flocco, M. M.; Cui, J.; Pergeo, R.; Rusconi, L.; Cristiani, C. Crystal structure of the tyrosine kinase domain of the hepatocyte growth factor receptor c-met and its complex with the microbial alkaloid K-252a. PNAS, 2003, 100, 12654-12659.
    • (2003) PNAS , vol.100 , pp. 12654-12659
    • Schierling, N.1    Knapp, S.2    Marconi, M.3    Flocco, M.M.4    Cui, J.5    Pergeo, R.6    Rusconi, L.7    Cristiani, C.8
  • 49
    • 0030945871 scopus 로고    scopus 로고
    • Structure of the tyrosine kinase domain of fibroblast growth factor 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 factor 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
  • 50
    • 0141521944 scopus 로고    scopus 로고
    • High throughput screening protein kinase assays optimized for reaction, binding, and detection totally within a 96-well plate
    • Pitt, A. M.; Lee, C. High throughput screening protein kinase assays optimized for reaction, binding, and detection totally within a 96-well plate. J. Biomol. Screening 1996, 1, 47-51.
    • (1996) J. Biomol. Screening , vol.1 , pp. 47-51
    • Pitt, A.M.1    Lee, C.2
  • 51
    • 0026567491 scopus 로고
    • SH2 domains prevent tyrosine dephosphorylation of the EGF receptor: Identification of Tyr992 as the high-affinity binding site for SH2 domains of phospholipase C gamma
    • Rotin, D.; Margolis, B.; Mohammadi, M.; Daly, R. J.; Daum, G.; Li, N.; Fischer, E. H.; Burgess, W. H.; Ullrich, A.; Schlessinger, J. SH2 domains prevent tyrosine dephosphorylation of the EGF receptor: identification of Tyr992 as the high-affinity binding site for SH2 domains of phospholipase C gamma. EMBO J. 1992, 11, 559-567.
    • (1992) EMBO J. , vol.11 , pp. 559-567
    • Rotin, D.1    Margolis, B.2    Mohammadi, M.3    Daly, R.J.4    Daum, G.5    Li, N.6    Fischer, E.H.7    Burgess, W.H.8    Ullrich, A.9    Schlessinger, J.10
  • 52
    • 10744227153 scopus 로고    scopus 로고
    • A new class of potent VEGF receptor tyrosine kinase inhibitors: Structure-activity relationships for a series of 9-alkoxymethyl-12-(3- hydroxypropyl)-indeno[2,1-a]pyrrolo[3,4-c]carbazole-5-ones and the identification of CEP-5214 and its dimethylglycine ester prodrug clinical candidate CEP-7055
    • Gingrich, D. E.; Reddy, D. R.; Iqbal, M. A.; Singh, J.; Aimone, L. D.; Angeles, T. S.; Albom, M.; Yang, S.; Meyer, S.; Robinson, C.; Ruggeri, B. A.;. Dionne, C. A.; Vaught, J. L.; Mallamo, J. P.; Hudkins, R. L. A new class of potent VEGF receptor tyrosine kinase inhibitors: structure-activity relationships for a series of 9-alkoxymethyl-12-(3-hydroxypropyl)-indeno[2,1-a] pyrrolo[3,4-c]carbazole-5-ones and the identification of CEP-5214 and its dimethylglycine ester prodrug clinical candidate CEP-7055. J. Med. Chem. 2003, 46, 5375-5388.
    • (2003) J. Med. Chem. , vol.46 , pp. 5375-5388
    • Gingrich, D.E.1    Reddy, D.R.2    Iqbal, M.A.3    Singh, J.4    Aimone, L.D.5    Angeles, T.S.6    Albom, M.7    Yang, S.8    Meyer, S.9    Robinson, C.10    Ruggeri, B.A.11    Dionne, C.A.12    Vaught, J.L.13    Mallamo, J.P.14    Hudkins, R.L.15


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.