Suberoylanilide hydroxamic acid, a potent histone deacetylase inhibitor; its X-ray crystal structure and solid state and solution studies of its Zn(II), Ni(II), Cu(II) and Fe(III) complexes

Darren M. Griffith, Béla Szocs, Tomás Keogh, Kyrill Yu Suponitsky, E. Farkas, P. Buglyó, Celine J. Marmion

Research output: Contribution to journalArticle

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Abstract

Reaction of the potent hydroxamate-based histone deacetylase (HDAC) inhibitor, suberoylanilide hydroxamic acid (SAHA), with hydrated metal salts of Fe(III), Cu(II), Ni(II) and Zn(II) yielded a tris-hydroxamato complex in the case of Fe(III) and bis-hydroxamato complexes in the case of Cu(II), Ni(II) and Zn(II) both in the solid state and in solution. Reaction of the secondary hydroxamic acid, N-Me-SAHA, also yielded a tris-hydroxamato complex in the case of Fe(III) and bis-hydroxamato complexes in the case of Cu(II), Ni(II) and Zn(II) in solution. These metal complexes have the hydroxamato moiety coordinated in an O,O′-bidentate fashion. Stability constants of the metal complexes formed with SAHA and N-Me-SAHA in a DMSO/H2O 70/30%(v/v) mixture are described. A novel crystal structure of SAHA together with a novel synthesis for N-Me-SAHA are also reported.

Original languageEnglish
Pages (from-to)763-769
Number of pages7
JournalJournal of Inorganic Biochemistry
Volume105
Issue number6
DOIs
Publication statusPublished - Jun 2011

Fingerprint

Histone Deacetylase Inhibitors
Crystal structure
X-Rays
X rays
Coordination Complexes
Hydroxamic Acids
Dimethyl Sulfoxide
vorinostat
Salts
Metals

Keywords

  • Anti-cancer agent
  • Histone deacetylase inhibitor
  • Hydroxamic acids
  • Metal complexes
  • Metalloenzyme

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry

Cite this

Suberoylanilide hydroxamic acid, a potent histone deacetylase inhibitor; its X-ray crystal structure and solid state and solution studies of its Zn(II), Ni(II), Cu(II) and Fe(III) complexes. / Griffith, Darren M.; Szocs, Béla; Keogh, Tomás; Suponitsky, Kyrill Yu; Farkas, E.; Buglyó, P.; Marmion, Celine J.

In: Journal of Inorganic Biochemistry, Vol. 105, No. 6, 06.2011, p. 763-769.

Research output: Contribution to journalArticle

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