The crystal and molecular structure of (R)-sirtinol-C26H22N2O2-a chemo-sensitive enhancer and ligand in metal complexes with important bio-inorganic applications

Ivan Bernal, Roger A. Lalancette, Ahmad Hudaihed, Pavel Kucheryavy

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Sirtinol is a known inhibitor of sirtuin proteins-a family of deacetylases involved in the physiology of aging. Its crystalline structure has never been determined except when bound to Fe(III) where it participates in the seven-fold coordination of the metal or to Cu(II) where it acts as a bidentate or tridentate ligand. Herein, we describe the structure of this important molecule, as follows: (a) the prevalent form of the keto-enol tautomerism in the solid state, and (b) in solution. Do they match? If not, how? The crystals of (R)-sirtinol are characterized by a large number of π-πbonded interactions linking molecules in infinite ribbons, which, in turn, are linked by additional π-πinteractions of a variety of types, and by hydrogen bonds. In the latter case, we confirm by NMR that the X-ray determined position of an important H atom is on a N atom rather than on an O, which is how the molecule is usually depicted.

Original languageEnglish (US)
Pages (from-to)315-321
Number of pages7
JournalZeitschrift fur Kristallographie - Crystalline Materials
Volume239
Issue number9-10
DOIs
StatePublished - Oct 1 2024
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • General Materials Science
  • Condensed Matter Physics
  • Inorganic Chemistry

Keywords

  • hydrogen bonds
  • physiology of aging
  • sirtinol
  • tautomeric forms
  • tumor growth inhibitors
  • π-πbonds

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