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Volumn 42, Issue 6, 2012, Pages 2103-2110

Evaluation of functional groups on amino acids in cyclic tetrapeptides in histone deacetylase inhibition

Author keywords

Chlamydocin; Epoxyketone; Functional group design; Histone deacetylase inhibitor

Indexed keywords

1,2 PHENYLENEDIAMINE; 2 AMINO 2 METHYLPROPIONIC ACID; 2 AMINO 8 (OXIRAN 2 YL) 8 OXOOCTANOIC ACID; AMINO ACID; BORIC ACID; CHLAMYDOCIN; EPOXYKETONE; HISTONE DEACETYLASE; HISTONE DEACETYLASE INHIBITOR; HYDROXAMIC ACID; KETONE DERIVATIVE; METHOXYMETHYLKETONE DERIVATIVE; PHENYLALANINE; PROLINE; TETRAPEPTIDE; THIOL DERIVATIVE; TRIFLUOROMETHYLKETONE; UNCLASSIFIED DRUG; ZINC;

EID: 84862757536     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-011-0947-6     Document Type: Article
Times cited : (17)

References (27)
  • 1
    • 33645892015 scopus 로고    scopus 로고
    • Chlamydocin analogs bearing carbonyl group as possible ligand toward zinc atom in histone deacetylases
    • 10.1016/j.bmc.2005.12.063 16439135 10.1016/j.bmc.2005.12.063 1:CAS:528:DC%2BD28XjtFGjur0%3D
    • MPI Bhuiyan T Kato T Okauchi, et al. 2006 Chlamydocin analogs bearing carbonyl group as possible ligand toward zinc atom in histone deacetylases Bioorg Med Chem 14 3438 3446 10.1016/j.bmc.2005.12.063 16439135 10.1016/j.bmc.2005.12.063 1:CAS:528:DC%2BD28XjtFGjur0%3D
    • (2006) Bioorg Med Chem , vol.14 , pp. 3438-3446
    • Bhuiyan, M.P.I.1    Kato, T.2    Okauchi, T.3
  • 2
    • 77955355838 scopus 로고    scopus 로고
    • Rational design and simple chemistry yield a superior, neuroprotective HDAC6 inhibitor, tubastin A
    • 10.1021/ja102758v 20614936 10.1021/ja102758v 1:CAS:528: DC%2BC3cXos1ers7k%3D
    • KV Butler J Kalin C Brochier G Vistoli B Langley AP Kozikowski 2010 Rational design and simple chemistry yield a superior, neuroprotective HDAC6 inhibitor, tubastin A J Am Chem Soc 132 10842 10846 10.1021/ja102758v 20614936 10.1021/ja102758v 1:CAS:528:DC%2BC3cXos1ers7k%3D
    • (2010) J Am Chem Soc , vol.132 , pp. 10842-10846
    • Butler, K.V.1    Kalin, J.2    Brochier, C.3    Vistoli, G.4    Langley, B.5    Kozikowski, A.P.6
  • 3
    • 0016366116 scopus 로고
    • Isolierung und Strukturaufklärung von Chlamydocin
    • 10.1002/hlca.19740570306 4857466 10.1002/hlca.19740570306 1:STN:280:DyaE2c7ntFCgtw%3D%3D
    • A Closse R Hugenin 1974 Isolierung und Strukturaufklärung von Chlamydocin Helv Chim Acta 57 533 545 10.1002/hlca.19740570306 4857466 10.1002/hlca.19740570306 1:STN:280:DyaE2c7ntFCgtw%3D%3D
    • (1974) Helv Chim Acta , vol.57 , pp. 533-545
    • Closse, A.1    Hugenin, R.2
  • 4
    • 10544250252 scopus 로고    scopus 로고
    • Apicidin: A novel antiprotozoal agent that inhibits parasite histone deacetylase
    • 8917558 10.1073/pnas.93.23.13143 1:CAS:528:DyaK28XmvV2qtrk%3D
    • SJ Darkin-Rattray AM Gurnett RW Myers, et al. 1996 Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase Proc Natl Acad Sci USA 93 13143 13147 8917558 10.1073/pnas.93.23.13143 1:CAS:528: DyaK28XmvV2qtrk%3D
    • (1996) Proc Natl Acad Sci USA , vol.93 , pp. 13143-13147
    • Darkin-Rattray, S.J.1    Gurnett, A.M.2    Myers, R.W.3
  • 5
    • 0035793107 scopus 로고    scopus 로고
    • Potent histone deacetylase inhibitors built from trichostatin A and cyclic tetrapeptide antibiotics including trapoxin
    • 11134513 10.1073/pnas.011405598 1:CAS:528:DC%2BD3MXkslKltQ%3D%3D
    • R Furumai Y Komatsu N Nishino, et al. 2001 Potent histone deacetylase inhibitors built from trichostatin A and cyclic tetrapeptide antibiotics including trapoxin Proc Natl Acad Sci USA 98 87 92 11134513 10.1073/pnas. 011405598 1:CAS:528:DC%2BD3MXkslKltQ%3D%3D
    • (2001) Proc Natl Acad Sci USA , vol.98 , pp. 87-92
    • Furumai, R.1    Komatsu, Y.2    Nishino, N.3
  • 6
    • 0036735385 scopus 로고    scopus 로고
    • FK228 (depsipeptide) as a natural prodrug that inhibits class1 histone deacetylases1
    • 12208741 1:CAS:528:DC%2BD38Xmslylu78%3D
    • R Furumai A Matsuyama M Kobashi 2002 FK228 (depsipeptide) as a natural prodrug that inhibits class1 histone deacetylases1 Cancer Res 62 4916 4921 12208741 1:CAS:528:DC%2BD38Xmslylu78%3D
    • (2002) Cancer Res , vol.62 , pp. 4916-4921
    • Furumai, R.1    Matsuyama, A.2    Kobashi, M.3
  • 7
    • 0036008097 scopus 로고    scopus 로고
    • Deacetylase enzymes: Biological functions and the use of small-molecule inhibitors
    • 11841934 10.1016/S1074-5521(02)00092-3 1:CAS:528:DC%2BD38XhtF2isLo%3D
    • CM Grozinger SL Schreiber 2002 Deacetylase enzymes: biological functions and the use of small-molecule inhibitors Chem Biol 9 3 16 11841934 10.1016/S1074-5521(02)00092-3 1:CAS:528:DC%2BD38XhtF2isLo%3D
    • (2002) Chem Biol , vol.9 , pp. 3-16
    • Grozinger, C.M.1    Schreiber, S.L.2
  • 8
    • 0034326799 scopus 로고    scopus 로고
    • Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21waf1/cip1 and gelsolin1
    • 11085529 1:CAS:528:DC%2BD3cXotV2lsLs%3D
    • JW Han SH Ahn SH Park, et al. 2000 Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21waf1/cip1 and gelsolin1 Cancer Res 60 6068 6074 11085529 1:CAS:528:DC%2BD3cXotV2lsLs%3D
    • (2000) Cancer Res , vol.60 , pp. 6068-6074
    • Han, J.W.1    Ahn, S.H.2    Park, S.H.3
  • 9
    • 0031244521 scopus 로고    scopus 로고
    • Nuclear histone acetylases and deacetylases and transcriptional regulation: HATS off to HDACs
    • 9667866 10.1016/S1367-5931(97)80066-X 1:CAS:528:DyaK2sXnt12mtL4%3D
    • CA Hassig SL Schreiber 1997 Nuclear histone acetylases and deacetylases and transcriptional regulation: HATS off to HDACs Curr Opin Chem Biol 1 300 308 9667866 10.1016/S1367-5931(97)80066-X 1:CAS:528:DyaK2sXnt12mtL4%3D
    • (1997) Curr Opin Chem Biol , vol.1 , pp. 300-308
    • Hassig, C.A.1    Schreiber, S.L.2
  • 10
    • 0015897498 scopus 로고
    • Structure of Cyl-2, a novel cyclotetrapeptide from Cylindrocladium scoparium
    • 10.1271/bbb1961.37.955 1:CAS:528:DyaE3sXktlagsr4%3D
    • A Hirota A Suzuki K Aizawa S Tamura 1973 Structure of Cyl-2, a novel cyclotetrapeptide from Cylindrocladium scoparium Agric Biol Chem 37 955 956 10.1271/bbb1961.37.955 1:CAS:528:DyaE3sXktlagsr4%3D
    • (1973) Agric Biol Chem , vol.37 , pp. 955-956
    • Hirota, A.1    Suzuki, A.2    Aizawa, K.3    Tamura, S.4
  • 11
    • 0015792162 scopus 로고
    • Isolation and biological activity of cyl-2, a metabolite of Cylindrocladium scoparium
    • 10.1271/bbb1961.37.643 1:CAS:528:DyaE3sXhsFKgsbo%3D
    • A Hirota A Suzuki H Suzuki S Tamura 1973 Isolation and biological activity of cyl-2, a metabolite of Cylindrocladium scoparium Agric Biol Chem 37 643 647 10.1271/bbb1961.37.643 1:CAS:528:DyaE3sXhsFKgsbo%3D
    • (1973) Agric Biol Chem , vol.37 , pp. 643-647
    • Hirota, A.1    Suzuki, A.2    Suzuki, H.3    Tamura, S.4
  • 12
    • 0015786862 scopus 로고
    • Characterization of four amino acids constituting cyl-2, a metabolite from Cylindrocladium scoparium
    • 10.1271/bbb1961.37.1185 1:CAS:528:DyaE3sXks1arsbk%3D
    • A Hirota A Suzuki S Tamura 1973 Characterization of four amino acids constituting cyl-2, a metabolite from Cylindrocladium scoparium Agric Biol Chem 37 1185 1189 10.1271/bbb1961.37.1185 1:CAS:528:DyaE3sXks1arsbk%3D
    • (1973) Agric Biol Chem , vol.37 , pp. 1185-1189
    • Hirota, A.1    Suzuki, A.2    Tamura, S.3
  • 13
    • 5344281161 scopus 로고    scopus 로고
    • Novel histone deacetylase inhibitors: Cyclic tetrapeptide with trifluoromethyl and pentafluoroethyl ketones
    • 10.1016/j.bmcl.2004.08.016 15454224 10.1016/j.bmcl.2004.08.016 1:CAS:528:DC%2BD2cXnvFWqt7s%3D
    • B Jose Y Oniki T Kato, et al. 2004 Novel histone deacetylase inhibitors: cyclic tetrapeptide with trifluoromethyl and pentafluoroethyl ketones Bioorg Med Chem Lett 14 5343 5346 10.1016/j.bmcl.2004.08.016 15454224 10.1016/j.bmcl.2004. 08.016 1:CAS:528:DC%2BD2cXnvFWqt7s%3D
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 5343-5346
    • Jose, B.1    Oniki, Y.2    Kato, T.3
  • 14
    • 0141855403 scopus 로고    scopus 로고
    • Phosphorus-based SAHA analogues as histone deacetylase inhibitors
    • 10.1021/ol035056n 12916979 10.1021/ol035056n 1:CAS:528: DC%2BD3sXlvFaktrg%3D
    • GV Kapustin G Fejér L Jennifer JL Gronlund, et al. 2003 Phosphorus-based SAHA analogues as histone deacetylase inhibitors Org Lett 5 3053 3056 10.1021/ol035056n 12916979 10.1021/ol035056n 1:CAS:528: DC%2BD3sXlvFaktrg%3D
    • (2003) Org Lett , vol.5 , pp. 3053-3056
    • Kapustin, G.V.1    Fejér, G.2    Jennifer, L.3    Gronlund, J.L.4
  • 15
    • 0027378351 scopus 로고
    • Trapoxin, an antitumor cyclic tetrapeptide, is an irreversible inhibitor of mammalian histone deacetylase
    • M Kijima M Yoshida K Suguta, et al. 1993 Trapoxin, an antitumor cyclic tetrapeptide, is an irreversible inhibitor of mammalian histone deacetylase J Biol Chem 268 22249 22435
    • (1993) J Biol Chem , vol.268 , pp. 22249-22435
    • Kijima, M.1    Yoshida, M.2    Suguta, K.3
  • 16
    • 0033000990 scopus 로고    scopus 로고
    • Histone acetylases and deacetylases in cell proliferation
    • 10072350 10.1016/S0959-437X(99)80006-9 1:CAS:528:DyaK1MXhsFSntL8%3D
    • T Kouzarides 1999 Histone acetylases and deacetylases in cell proliferation Curr Opin Genet Dev 9 40 48 10072350 10.1016/S0959-437X(99)80006-9 1:CAS:528:DyaK1MXhsFSntL8%3D
    • (1999) Curr Opin Genet Dev , vol.9 , pp. 40-48
    • Kouzarides, T.1
  • 17
    • 0035024737 scopus 로고    scopus 로고
    • Histone deacetylase: A target for antiproliferative and antiprotozoal agents
    • 11172676 1:CAS:528:DC%2BD3MXhtVSgt74%3D
    • PT Meinke P Liberator 2001 Histone deacetylase: a target for antiproliferative and antiprotozoal agents Curr Med Chem 8 211 235 11172676 1:CAS:528:DC%2BD3MXhtVSgt74%3D
    • (2001) Curr Med Chem , vol.8 , pp. 211-235
    • Meinke, P.T.1    Liberator, P.2
  • 18
    • 0346025398 scopus 로고    scopus 로고
    • Cyclic tetrapeptides bearing a sulfhydryl group potently inhibit histone deacetylases
    • 10.1021/ol036098e 14682769 10.1021/ol036098e 1:CAS:528: DC%2BD3sXpsFOku7Y%3D
    • N Nishino B Jose S Okamura, et al. 2003 Cyclic tetrapeptides bearing a sulfhydryl group potently inhibit histone deacetylases Org Lett 5 5079 5082 10.1021/ol036098e 14682769 10.1021/ol036098e 1:CAS:528:DC%2BD3sXpsFOku7Y%3D
    • (2003) Org Lett , vol.5 , pp. 5079-5082
    • Nishino, N.1    Jose, B.2    Okamura, S.3
  • 19
    • 1942502754 scopus 로고    scopus 로고
    • Synthesis and histone deacetylase inhibitory activity of cyclic tetrapeptides containing a retrohydroxamate as zinc ligand
    • 10.1016/j.bmcl.2004.03.018 15109626 10.1016/j.bmcl.2004.03.018 1:CAS:528:DC%2BD2cXjsVKhsbg%3D
    • N Nishino D Yoshikawa LA Watanabe, et al. 2004 Synthesis and histone deacetylase inhibitory activity of cyclic tetrapeptides containing a retrohydroxamate as zinc ligand Bioorg Med Chem lett 14 2427 2431 10.1016/j.bmcl.2004.03.018 15109626 10.1016/j.bmcl.2004.03.018 1:CAS:528:DC%2BD2cXjsVKhsbg%3D
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 2427-2431
    • Nishino, N.1    Yoshikawa, D.2    Watanabe, L.A.3
  • 20
    • 0033551152 scopus 로고    scopus 로고
    • A synthetic inhibitor of histone deacetylase, MS-27-275, with marked in vivo antitumor activity against human tumors
    • 10200307 10.1073/pnas.96.8.4592 1:CAS:528:DyaK1MXjs1ylsbk%3D
    • A Saito T Yamashita Y Mariko 1999 A synthetic inhibitor of histone deacetylase, MS-27-275, with marked in vivo antitumor activity against human tumors Proc Natl Acad Sci USA 96 4592 4597 10200307 10.1073/pnas.96.8.4592 1:CAS:528:DyaK1MXjs1ylsbk%3D
    • (1999) Proc Natl Acad Sci USA , vol.96 , pp. 4592-4597
    • Saito, A.1    Yamashita, T.2    Mariko, Y.3
  • 21
    • 0033614993 scopus 로고    scopus 로고
    • Synthesis and histone deacetylase inhibitory activity of new benzamide derivatives
    • 10.1021/jm980565u 10425110 10.1021/jm980565u 1:CAS:528:DyaK1MXktVOrtr8%3D
    • T Suzuki T Ando K Tsuchiya, et al. 1999 Synthesis and histone deacetylase inhibitory activity of new benzamide derivatives J Med Chem 42 3001 3003 10.1021/jm980565u 10425110 10.1021/jm980565u 1:CAS:528:DyaK1MXktVOrtr8%3D
    • (1999) J Med Chem , vol.42 , pp. 3001-3003
    • Suzuki, T.1    Ando, T.2    Tsuchiya, K.3
  • 22
    • 2442597872 scopus 로고    scopus 로고
    • Thiol-based SAHA analogues as potent histone deacetylase Inhibitors
    • 10.1016/j.bmcl.2004.03.063 15149697 10.1016/j.bmcl.2004.03.063 1:CAS:528:DC%2BD2cXktVeqsrc%3D
    • T Suzuki A Kouketsu A Matsuura, et al. 2004 Thiol-based SAHA analogues as potent histone deacetylase Inhibitors Bioorg Med Chem Lett 14 3313 3317 10.1016/j.bmcl.2004.03.063 15149697 10.1016/j.bmcl.2004.03.063 1:CAS:528:DC%2BD2cXktVeqsrc%3D
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 3313-3317
    • Suzuki, T.1    Kouketsu, A.2    Matsuura, A.3
  • 23
    • 65649125951 scopus 로고    scopus 로고
    • Design, synthesis, and biological activity of boronic acid-based histone deacetylase inhibitors
    • 10.1021/jm900125m 19419205 10.1021/jm900125m 1:CAS:528: DC%2BD1MXksV2ju7Y%3D
    • N Suzuki T Suzuki Y Ota, et al. 2009 Design, synthesis, and biological activity of boronic acid-based histone deacetylase inhibitors J Med Chem 52 2909 2922 10.1021/jm900125m 19419205 10.1021/jm900125m 1:CAS:528: DC%2BD1MXksV2ju7Y%3D
    • (2009) J Med Chem , vol.52 , pp. 2909-2922
    • Suzuki, N.1    Suzuki, T.2    Ota, Y.3
  • 24
    • 25444469045 scopus 로고    scopus 로고
    • Total synthesis of cyclic tetrapeptide FR235222, a potent immunosuppressant that inhibits mammalian histone deacetylases
    • 10.1021/ol050991r 15957944 10.1021/ol050991r 1:CAS:528: DC%2BD2MXksVWqsL8%3D
    • W Xie B Zou D Pei D Ma 2005 Total synthesis of cyclic tetrapeptide FR235222, a potent immunosuppressant that inhibits mammalian histone deacetylases Org Lett 7 2775 2777 10.1021/ol050991r 15957944 10.1021/ol050991r 1:CAS:528:DC%2BD2MXksVWqsL8%3D
    • (2005) Org Lett , vol.7 , pp. 2775-2777
    • Xie, W.1    Zou, B.2    Pei, D.3    Ma, D.4
  • 25
    • 0024996768 scopus 로고
    • Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A
    • 2211619 1:CAS:528:DyaK3cXlvVyqsrY%3D
    • M Yoshida M Kijima M Akita T Beppu 1990 Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A J Biol Chem 265 17174 17179 2211619 1:CAS:528:DyaK3cXlvVyqsrY%3D
    • (1990) J Biol Chem , vol.265 , pp. 17174-17179
    • Yoshida, M.1    Kijima, M.2    Akita, M.3    Beppu, T.4
  • 26
    • 0141885037 scopus 로고    scopus 로고
    • From discovery to the coming generation of histone deacetylase inhibitors
    • 10.2174/092986708784049612 14529478 10.2174/0929867033456602 1:CAS:528:DC%2BD3sXotFKlsLc%3D
    • M Yoshida A Matsuayama Y Komatsu N Nishino 2003 From discovery to the coming generation of histone deacetylase inhibitors Curr Med Chem 10 2351 2358 10.2174/092986708784049612 14529478 10.2174/0929867033456602 1:CAS:528:DC%2BD3sXotFKlsLc%3D
    • (2003) Curr Med Chem , vol.10 , pp. 2351-2358
    • Yoshida, M.1    Matsuayama, A.2    Komatsu, Y.3    Nishino, N.4


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