메뉴 건너뛰기




Volumn 72, Issue 10, 2008, Pages 2623-2631

Hydroxamic acid derivatives of mycophenolic acid inhibit histone deacetylase at the cellular level

Author keywords

tubulin deacetylase (TDAC); HDAC inhibitors synthesis; Histone deacetylase (HDAC); Inosine monophosphate dehydrogenase (IMPDH); Mycophenolic acid (MPA)

Indexed keywords

BINDING ENERGY; BINDING SITES; CELL PROLIFERATION; ENZYMES; ORGANIC ACIDS;

EID: 55049101683     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.80303     Document Type: Article
Times cited : (12)

References (36)
  • 1
    • 0000190025 scopus 로고
    • The molecular constitution of mycophenolic acid, a metabolite of Penicillium brevi-compactum DIERCKX. III. Further observations on the structural formula for mycophenolic acid
    • Birkinshaw, J. H., Raistrick, H., and Ross, D. J., The molecular constitution of mycophenolic acid, a metabolite of Penicillium brevi-compactum DIERCKX. III. Further observations on the structural formula for mycophenolic acid. Biochem. J., 50, 630-634 (1952).
    • (1952) Biochem. J , vol.50 , pp. 630-634
    • Birkinshaw, J.H.1    Raistrick, H.2    Ross, D.J.3
  • 2
    • 33750293642 scopus 로고    scopus 로고
    • Therapeutic drug monitoring of mycophenolic acid in solid organ transplant patients treated with mycophenolate mofetil: Review of the literature
    • Arns, W., Cibrik, D. M., Walker, R. G., Mourad, G., Budde, K., Mueller, E. A., and Vincenti, F., Therapeutic drug monitoring of mycophenolic acid in solid organ transplant patients treated with mycophenolate mofetil: review of the literature. Transplantation, 82, 1004-1012 (2006).
    • (2006) Transplantation , vol.82 , pp. 1004-1012
    • Arns, W.1    Cibrik, D.M.2    Walker, R.G.3    Mourad, G.4    Budde, K.5    Mueller, E.A.6    Vincenti, F.7
  • 3
    • 0025961794 scopus 로고
    • Expression of human IMP dehydrogenase types I and II in Escherichia coli and distribution in human normal lymphocytes and leukemia cell lines
    • Konno, Y., Natsumeda, Y., Nagai, M., Yamaji, Y., Ohno, S., Suzuki, K., and Weber, G., Expression of human IMP dehydrogenase types I and II in Escherichia coli and distribution in human normal lymphocytes and leukemia cell lines. J. Biol. Chem., 266, 506-509 (1991).
    • (1991) J. Biol. Chem , vol.266 , pp. 506-509
    • Konno, Y.1    Natsumeda, Y.2    Nagai, M.3    Yamaji, Y.4    Ohno, S.5    Suzuki, K.6    Weber, G.7
  • 4
    • 0026378294 scopus 로고
    • Selective up-regulation of type II inosine 5′-monophosphate dehydrogenase messenger RNA expression in human leukemias
    • Nagai, M., Natsumeda, Y., Konno, Y., Hoffman, R., Irino, S., and Weber, G., Selective up-regulation of type II inosine 5′-monophosphate dehydrogenase messenger RNA expression in human leukemias. Cancer Res., 51, 3886-3890 (1991).
    • (1991) Cancer Res , vol.51 , pp. 3886-3890
    • Nagai, M.1    Natsumeda, Y.2    Konno, Y.3    Hoffman, R.4    Irino, S.5    Weber, G.6
  • 7
    • 10844264316 scopus 로고    scopus 로고
    • Differentiation of human prostate cancer PC-3 cells induced by inhibitors of inosine 5′-monophosphate dehydrogenase
    • Floryk, D., Tollaksen, S. L., Giometti, C. S., and Huberman, E., Differentiation of human prostate cancer PC-3 cells induced by inhibitors of inosine 5′-monophosphate dehydrogenase. Cancer Res., 64, 9049-9056 (2004).
    • (2004) Cancer Res , vol.64 , pp. 9049-9056
    • Floryk, D.1    Tollaksen, S.L.2    Giometti, C.S.3    Huberman, E.4
  • 8
    • 29244450493 scopus 로고    scopus 로고
    • Differentiation of androgen-independent prostate cancer PC-3 cells is associated with increased nuclear factor-kappaB activity
    • Floryk, D., and Huberman, E., Differentiation of androgen-independent prostate cancer PC-3 cells is associated with increased nuclear factor-kappaB activity. Cancer Res., 65, 11588-11596 (2005).
    • (2005) Cancer Res , vol.65 , pp. 11588-11596
    • Floryk, D.1    Huberman, E.2
  • 9
    • 28844473202 scopus 로고    scopus 로고
    • Mycophenolic acid-induced replication arrest, differentiation markers and cell death of androgen-independent prostate cancer cells DU145
    • Floryk, D., and Huberman, E., Mycophenolic acid-induced replication arrest, differentiation markers and cell death of androgen-independent prostate cancer cells DU145. Cancer Lett., 231, 20-29 (2006).
    • (2006) Cancer Lett , vol.231 , pp. 20-29
    • Floryk, D.1    Huberman, E.2
  • 10
    • 33646439982 scopus 로고    scopus 로고
    • Identification of type I inosine monophosphate dehydrogenase as an antiangiogenic drug target
    • Chong, C. R., Qian, D. Z., Pan, F., Wei, Y., Pili, R., Sullivan Jr., D. J., and Liu, J. O., Identification of type I inosine monophosphate dehydrogenase as an antiangiogenic drug target. J. Med. Chem., 49, 2677-2680 (2006).
    • (2006) J. Med. Chem , vol.49 , pp. 2677-2680
    • Chong, C.R.1    Qian, D.Z.2    Pan, F.3    Wei, Y.4    Pili, R.5    Sullivan Jr., D.J.6    Liu, J.O.7
  • 12
    • 33644983882 scopus 로고    scopus 로고
    • IMP dehydrogenase inhibitor mycophenolate mofetil induces caspase-dependent apoptosis and cell cycle inhibition in multiple myeloma cells
    • Takabe, N., Cheng, X., Fandy, T. E., Srivastava, R. K., Wu, S., Shankar, S., Bauer, K., Shaughnessy, J., and Tricot, G., IMP dehydrogenase inhibitor mycophenolate mofetil induces caspase-dependent apoptosis and cell cycle inhibition in multiple myeloma cells. Mol. Cancer Ther., 5, 457-466 (2006).
    • (2006) Mol. Cancer Ther , vol.5 , pp. 457-466
    • Takabe, N.1    Cheng, X.2    Fandy, T.E.3    Srivastava, R.K.4    Wu, S.5    Shankar, S.6    Bauer, K.7    Shaughnessy, J.8    Tricot, G.9
  • 13
    • 0034610814 scopus 로고    scopus 로고
    • The language of covalent histone modifications
    • Strahl, B. D., and Allis, C. D., The language of covalent histone modifications. Nature, 403, 41-45 (2000).
    • (2000) Nature , vol.403 , pp. 41-45
    • Strahl, B.D.1    Allis, C.D.2
  • 16
    • 33645950778 scopus 로고    scopus 로고
    • Histone deacetylase inhibitors: Multifunctional anticancer agents
    • Liu, T., Kuljaca, S., Tee, A., and Marshall, G. M., Histone deacetylase inhibitors: multifunctional anticancer agents. Cancer Treat. Rev., 32, 157-165 (2006).
    • (2006) Cancer Treat. Rev , vol.32 , pp. 157-165
    • Liu, T.1    Kuljaca, S.2    Tee, A.3    Marshall, G.M.4
  • 18
    • 10844248177 scopus 로고    scopus 로고
    • Phase I study of oral CI-994 in combination with carboplatin and paclitaxel in the treatment of patients with advanced solid tumors
    • Pauer, L., Olivares, J., Cunningham, C., Williams, A., Grove, W., Kraker, A., Olson, S., and Nemunaitis, J., Phase I study of oral CI-994 in combination with carboplatin and paclitaxel in the treatment of patients with advanced solid tumors. Cancer Invest., 22, 886-896 (2004).
    • (2004) Cancer Invest , vol.22 , pp. 886-896
    • Pauer, L.1    Olivares, J.2    Cunningham, C.3    Williams, A.4    Grove, W.5    Kraker, A.6    Olson, S.7    Nemunaitis, J.8
  • 19
    • 33745629366 scopus 로고    scopus 로고
    • results of a phase II randomized, double-blind, placebo-controlled, multicenter study
    • Gemcitabine plus CI-994 offers no advantage over gemcitabine alone in the treatment of patients with advanced pancreatic cancer
    • Richards, D. A., Boehm, K. A., Waterhouse, D. M., Wagener, D. J., Krishnamurthi, S. S., Rosemurgy, A., Grove, W., Mackonald, K., Gulyas, S., Clark, M., and Dasse, K. D., Gemcitabine plus CI-994 offers no advantage over gemcitabine alone in the treatment of patients with advanced pancreatic cancer: results of a phase II randomized, double-blind, placebo-controlled, multicenter study. Ann. Oncol., 17, 1096-1102 (2006).
    • (2006) Ann. Oncol , vol.17 , pp. 1096-1102
    • Richards, D.A.1    Boehm, K.A.2    Waterhouse, D.M.3    Wagener, D.J.4    Krishnamurthi, S.S.5    Rosemurgy, A.6    Grove, W.7    Mackonald, K.8    Gulyas, S.9    Clark, M.10    Dasse, K.D.11
  • 21
    • 0024996768 scopus 로고
    • Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A
    • Yoshida, M., Kijima, M., Akita, M., and Beppu, T., Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A. J. Biol. Chem., 265, 17174-17179 (1990).
    • (1990) J. Biol. Chem , vol.265 , pp. 17174-17179
    • Yoshida, M.1    Kijima, M.2    Akita, M.3    Beppu, T.4
  • 22
    • 0038522853 scopus 로고    scopus 로고
    • Multidimensional chemical genetic analysis of diversity-oriented synthesis-derived deacetylase inhibitors using cell-based assays
    • Haggarty, S. J., Koeller, K. M., Wong, J. C., Butcher, R. A., and Schreiber, S. L., Multidimensional chemical genetic analysis of diversity-oriented synthesis-derived deacetylase inhibitors using cell-based assays. Chem. Biol., 10, 383-396 (2003).
    • (2003) Chem. Biol , vol.10 , pp. 383-396
    • Haggarty, S.J.1    Koeller, K.M.2    Wong, J.C.3    Butcher, R.A.4    Schreiber, S.L.5
  • 25
    • 37349017604 scopus 로고    scopus 로고
    • Dual inhibitors of inosine monophosphate dehydrogenase and histone deacetylases for cancer treatment
    • Cheng, L., Wilson, D., Jayaram, H. N., and Pankiewicz, K. W., Dual inhibitors of inosine monophosphate dehydrogenase and histone deacetylases for cancer treatment. J. Med. Chem., 50, 6685-6691 (2007).
    • (2007) J. Med. Chem , vol.50 , pp. 6685-6691
    • Cheng, L.1    Wilson, D.2    Jayaram, H.N.3    Pankiewicz, K.W.4
  • 26
    • 33847657556 scopus 로고    scopus 로고
    • Psammaplin A is a natural prodrug that inhibits class I histone deacetylase
    • Kim, D. H., Shin, J., and Kwon, H. J., Psammaplin A is a natural prodrug that inhibits class I histone deacetylase. Exp. Mol. Med., 39, 47-55 (2007).
    • (2007) Exp. Mol. Med , vol.39 , pp. 47-55
    • Kim, D.H.1    Shin, J.2    Kwon, H.J.3
  • 27
    • 0034641457 scopus 로고    scopus 로고
    • A convenient method for the preparation of hydroxamic acids
    • Reddy, A. S., Kumar, S., and Reddy, R., A convenient method for the preparation of hydroxamic acids. Tetrahedron Lett., 41, 6285-6288 (2000).
    • (2000) Tetrahedron Lett , vol.41 , pp. 6285-6288
    • Reddy, A.S.1    Kumar, S.2    Reddy, R.3
  • 28
    • 0025281073 scopus 로고
    • Bioavailability improvement of mycophenolic acid through amino ester derivatization
    • Lee, W. A., Gu, L., Miksztal, A. R., Chu, N., Leung, K., and Nelson, P. H., Bioavailability improvement of mycophenolic acid through amino ester derivatization. Pharm. Res., 7, 161-166 (1990).
    • (1990) Pharm. Res , vol.7 , pp. 161-166
    • Lee, W.A.1    Gu, L.2    Miksztal, A.R.3    Chu, N.4    Leung, K.5    Nelson, P.H.6
  • 30
    • 0036651788 scopus 로고    scopus 로고
    • Recent advances in the discovery of small molecule histone deacetylase inhibitors
    • Remiszewski, S. W., Recent advances in the discovery of small molecule histone deacetylase inhibitors. Curr. Opin. Drug Discov. Devel., 5, 487-499 (2002).
    • (2002) Curr. Opin. Drug Discov. Devel , vol.5 , pp. 487-499
    • Remiszewski, S.W.1
  • 31
    • 4344656352 scopus 로고    scopus 로고
    • Detection of the mycophenolate-inhibited form of IMP dehydrogenase in vivo
    • McPhillips, C. C., Hyle, J. W., and Reines, D., Detection of the mycophenolate-inhibited form of IMP dehydrogenase in vivo. Proc. Natl. Acad. Sci. USA, 101, 12171-12176 (2004).
    • (2004) Proc. Natl. Acad. Sci. USA , vol.101 , pp. 12171-12176
    • McPhillips, C.C.1    Hyle, J.W.2    Reines, D.3
  • 32
    • 33644872520 scopus 로고    scopus 로고
    • Regulation of the interaction of inosine monophosphate dehydrogenase with mycophenolic acid by GTP
    • Ji, Y., Gu, J., Makhov, A. M., Griffith, J. D., and Mitchell, B. S., Regulation of the interaction of inosine monophosphate dehydrogenase with mycophenolic acid by GTP. J. Biol. Chem., 281, 206-212 (2006).
    • (2006) J. Biol. Chem , vol.281 , pp. 206-212
    • Ji, Y.1    Gu, J.2    Makhov, A.M.3    Griffith, J.D.4    Mitchell, B.S.5
  • 33
    • 33748519900 scopus 로고    scopus 로고
    • structural schizophrenia and an unusual base
    • IMP dehydrogenase
    • Hedstrom, L., and Gan, L., IMP dehydrogenase: structural schizophrenia and an unusual base. Curr. Opin. Chem. Biol., 10, 520-526 (2006).
    • (2006) Curr. Opin. Chem. Biol , vol.10 , pp. 520-526
    • Hedstrom, L.1    Gan, L.2
  • 35
    • 55049119252 scopus 로고
    • U.S. Patent, 5380879 Jan. 10
    • Sjogrren, E. B., U.S. Patent, 5380879 (Jan. 10, 1995).
    • (1995)
    • Sjogrren, E.B.1
  • 36
    • 33847258674 scopus 로고    scopus 로고
    • Discovery and development of SAHA as an anticancer agent
    • Marks, P. A., Discovery and development of SAHA as an anticancer agent. Oncogene, 26, 1351-1356 (2007).
    • (2007) Oncogene , vol.26 , pp. 1351-1356
    • Marks, P.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.