메뉴 건너뛰기




Volumn 129, Issue 10, 2007, Pages 3007-3012

Molecular insights into azumamide E histone deacetylases inhibitory activity

Author keywords

[No Author keywords available]

Indexed keywords

ANTITUMOR AGENTS; AZUMAMIDES; HISTONE DEACETYLASE (HDAC); RECEPTORS;

EID: 33947239221     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0686256     Document Type: Article
Times cited : (89)

References (60)
  • 8
    • 20344392202 scopus 로고    scopus 로고
    • Angew. Chem., Int. Ed. 2005, 44, 3186-3216.
    • (2005) Chem., Int. Ed , vol.44 , pp. 3186-3216
    • Angew1
  • 11
    • 33845199114 scopus 로고    scopus 로고
    • Isolation: Nakao, Y.; Yoshida, S.; Matsunaga, S.; Shindoh, N.; Terada, Y.; Nagai, K.; Yamashita, J. K.; Ganesan, A.; van Soest, R. W. M.; Fusetani, N. Angew. Chem., Int. Ed. 2006, 45, 7553-7557.
    • (a) Isolation: Nakao, Y.; Yoshida, S.; Matsunaga, S.; Shindoh, N.; Terada, Y.; Nagai, K.; Yamashita, J. K.; Ganesan, A.; van Soest, R. W. M.; Fusetani, N. Angew. Chem., Int. Ed. 2006, 45, 7553-7557.
  • 12
    • 33845202563 scopus 로고    scopus 로고
    • Synthesis: Izzo, I.; Maulucci, N.; Bifulco, G.; De Riccardis, F. Angew. Chem., Int. Ed. 2006, 45, 7557-7560.
    • (b) Synthesis: Izzo, I.; Maulucci, N.; Bifulco, G.; De Riccardis, F. Angew. Chem., Int. Ed. 2006, 45, 7557-7560.
  • 24
    • 0014543875 scopus 로고    scopus 로고
    • Shemyakin, M. M.; Ovchinnikov, Yu, A.; Ivanov, V. T. Angew. Chem., Int. Ed. 1969, 8, 492-499.
    • (a) Shemyakin, M. M.; Ovchinnikov, Yu, A.; Ivanov, V. T. Angew. Chem., Int. Ed. 1969, 8, 492-499.
  • 34
    • 33947278082 scopus 로고    scopus 로고
    • 13C NMR spectrometry) measured on the synthetic sample were virtually indistinguishable from those reported for the natural product.
    • 13C NMR spectrometry) measured on the synthetic sample were virtually indistinguishable from those reported for the natural product.
  • 35
    • 33947253712 scopus 로고    scopus 로고
    • Since there is no X-ray structure of human HDAC1 available now, we have used the monomer form of the HDLP X-ray structure as receptor model. A sequence alignment shows a 35.2% sequence identity of HDLP and human HDAC1. The residues around the HDLP zinc-binding site are completely conservedjn human HDAC1 and all of the hydrophobic residues that make up the 11 Å channel in HDLP are identical in HDAC1. Most of the residues making up the 14 Å internal cavity are either identical or conservatively substituted in HDAC1 and, as can be expected from the high degree of sequence similarity, HDAC has the same structural features of HDLP described above.
    • Since there is no X-ray structure of human HDAC1 available now, we have used the monomer form of the HDLP X-ray structure as receptor model. A sequence alignment shows a 35.2% sequence identity of HDLP and human HDAC1. The residues around the HDLP zinc-binding site are completely conservedjn human HDAC1 and all of the hydrophobic residues that make up the 11 Å channel in HDLP are identical in HDAC1. Most of the residues making up the 14 Å internal cavity are either identical or conservatively substituted in HDAC1 and, as can be expected from the high degree of sequence similarity, HDAC has the same structural features of HDLP described above.
  • 36
    • 33947192740 scopus 로고    scopus 로고
    • Both the β-amino acid stereogenic centers were inverted to retain the same relative configuration of the 3-amino-2-methyl-5-nonendioic acid
    • Both the β-amino acid stereogenic centers were inverted to retain the same relative configuration of the 3-amino-2-methyl-5-nonendioic acid.
  • 39
    • 0035361402 scopus 로고    scopus 로고
    • In a recently reported SAR study on cyclic hydroxamic acid containing cyclopeptides (designed as hybrid of trichostatin and trapoxin, see: Komatsu, Y, Tomizaki, K.-Y, Tsukamoto, M, Kato, T, Nishino, N, Sato, S, Yamori, T, Tsuruo, T, Furumai, R, Yoshida, M, Horinouchi, S, Hayashi, H. Cancer Res. 2001, 61, 4459-4466, the HDAC inhibitory potency of different amino acid D/L combinations was directly related to the hydrophobicity of the molecules (higher hydrophobicity meant higher membrane permeability, This assumption contrasted with the weak activity (2 orders of magnitude lower) observed for one of the synthesized derivatives showing HPLC retention time comparable with those of the cognate compounds, We believe that biological activity should be, more appropriately, attributable to the tetrapeptide- receptor interaction modes. Our studies clarify some aspects of the binding at molecular level
    • In a recently reported SAR study on cyclic hydroxamic acid containing cyclopeptides (designed as hybrid of trichostatin and trapoxin, see: Komatsu, Y.; Tomizaki, K.-Y.; Tsukamoto, M.; Kato, T.; Nishino, N.; Sato, S.; Yamori, T.; Tsuruo, T.; Furumai, R.; Yoshida, M.; Horinouchi, S.; Hayashi, H. Cancer Res. 2001, 61, 4459-4466), the HDAC inhibitory potency of different amino acid D/L combinations was directly related to the hydrophobicity of the molecules (higher hydrophobicity meant higher membrane permeability). This assumption contrasted with the weak activity (2 orders of magnitude lower) observed for one of the synthesized derivatives (showing HPLC retention time comparable with those of the cognate compounds). We believe that biological activity should be, more appropriately, attributable to the tetrapeptide- receptor interaction modes. Our studies clarify some aspects of the binding at molecular level.
  • 40
    • 0029849456 scopus 로고    scopus 로고
    • The term chiroselective is used in opposition to nonspecific. Typical nonspecific biological actions are exerted on membranes. For the action of enantiomers of bioactive compounds on nonspecific target, see, for example
    • The term "chiroselective" is used in opposition to "nonspecific". Typical nonspecific biological actions are exerted on membranes. For the action of enantiomers of bioactive compounds on nonspecific target, see, for example: Juvvadi, P.; Vunnam, S.; Merrifield, R. B. J. Am. Chem. Soc. 1996, 118, 8989-8997.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 8989-8997
    • Juvvadi, P.1    Vunnam, S.2    Merrifield, R.B.3
  • 44
    • 0032852288 scopus 로고    scopus 로고
    • For the action of enantiomers of bioactive compounds on chiroselective target, see, for example: Bednarek, M. A.; Silva, M. V.; Arison, B.; MacNeil, T.; Kalyani, R. N.; Huang, R.-R. C.; Weinberg, D. H. Peptides 1999, 20, 401-409 (in which is described a significant drop of potency of the enantio-analog of the cyclic peptide MT-II).
    • For the action of enantiomers of bioactive compounds on chiroselective target, see, for example: Bednarek, M. A.; Silva, M. V.; Arison, B.; MacNeil, T.; Kalyani, R. N.; Huang, R.-R. C.; Weinberg, D. H. Peptides 1999, 20, 401-409 (in which is described a significant drop of potency of the enantio-analog of the cyclic peptide MT-II).
  • 45
    • 0028114289 scopus 로고    scopus 로고
    • Guichard, G.; Benkirane, N.; Zeder-Lutz, G.; Van Regenmortel, M. H. V.; Briand, J.-P.; Muller, S. Proc. Natl Acad. Sci. U.S.A. 1994, 91, 9765-9769 (in which is described the immunoglobulin IgG3 response on an enantiomeric form of an immunogenic peptide. Interestingly, no cross-response was observed for IgG1, IgG2a, and IgG2b antibodies).
    • Guichard, G.; Benkirane, N.; Zeder-Lutz, G.; Van Regenmortel, M. H. V.; Briand, J.-P.; Muller, S. Proc. Natl Acad. Sci. U.S.A. 1994, 91, 9765-9769 (in which is described the immunoglobulin IgG3 response on an enantiomeric form of an immunogenic peptide. Interestingly, no cross-response was observed for IgG1, IgG2a, and IgG2b antibodies).
  • 55
    • 33947250467 scopus 로고    scopus 로고
    • H131, H132, and Y297 are not shown in Figures 5-7 because they are too deep in the channel. They are reported (in the 3D models of the interaction between 5 and 8 with the HDLP binding site) in Figure S3 and S4 of the Supporting Information
    • H131, H132, and Y297 are not shown in Figures 5-7 because they are too deep in the channel. They are reported (in the 3D models of the interaction between 5 and 8 with the HDLP binding site) in Figure S3 and S4 of the Supporting Information.
  • 57
    • 0037142335 scopus 로고    scopus 로고
    • 50: 200 ± 100 nM) can be found in Woo, S. H.; Frechette, S.; Khalil, E. A.; Bouchain, G.; Vaisburg, A.; Bernstein, N.; Moradei, O.; Leit, S.; Allan, M.; Fournel, M.; Trachy-Bourget, M.-C.; Li, Z.; Besterman, J. M.; Delorme, D. J. Med. Chem. 2002, 45, 2877-2885.
    • 50: 200 ± 100 nM) can be found in Woo, S. H.; Frechette, S.; Khalil, E. A.; Bouchain, G.; Vaisburg, A.; Bernstein, N.; Moradei, O.; Leit, S.; Allan, M.; Fournel, M.; Trachy-Bourget, M.-C.; Li, Z.; Besterman, J. M.; Delorme, D. J. Med. Chem. 2002, 45, 2877-2885.
  • 59
    • 0032484904 scopus 로고    scopus 로고
    • Magnaghi, J. L.; Groisman, R.; Naguibneva, I.; Robin, P.; Lorain, S.; Le, Villain, J. P.; Troalen, F.; Trouche, D.; Harel-Bellan, A. Nature 1998, 391, 601-605.
    • (b) Magnaghi, J. L.; Groisman, R.; Naguibneva, I.; Robin, P.; Lorain, S.; Le, Villain, J. P.; Troalen, F.; Trouche, D.; Harel-Bellan, A. Nature 1998, 391, 601-605.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.