Temperature Dependence of the Rigid-Body Motion of Anthraquinone

Fu, Yigang; Brock, Carolyn Pratt

doi:10.1107/s0108768197013414

Cited by 19 publications

(23 citation statements)

References 18 publications

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“…The structure is strongly influenced by the size and polarity of the side chains attached to the anthraquinone rings. In general, anthraquinones with small lateral side chains pack as infinite stacked columns that are usually slanted (Kingsford-Adaboh & Kashino, 1995;Il'in et al, 1975;Janczak, 1995;Fu & Brock, 1998), similar to the situation found here in anthraquinones E and F (Figs. 3 and 4).…”

Section: Figuresupporting

confidence: 72%

Structure of a stacked anthraquinone–DNA complex

et al. 2010

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PDB Reference: anthraquinone-DNA complex, 3gdd.NDB Reference: anthraquinone-DNA complex, DD0106.The crystal structure of the telomeric sequence d(U Br AGG) interacting with an anthraquinone derivative has been solved by MAD. In all previously studied complexes of intercalating drugs, the drug is usually sandwiched between two DNA base pairs. Instead, the present structure looks like a crystal of stacked anthraquinone molecules in which isolated base pairs are intercalated. Unusual base pairs are present in the structure, such as GÁG and AÁU Br reverse WatsonCrick base pairs.

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Section: Figuresupporting

confidence: 72%

Structure of a stacked anthraquinone–DNA complex

et al. 2010

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“…Our structure, measured at 100 K, is characterized by non-centrosymmetric P2 1 2 1 2 1 space-group symmetry. All of the studied molecules are planar with the C-C bond lengths in the approximate range 1.37-1.42 Å , comparable to those of the anthracene (Ponomarev & Shilov, 1983) and anthraquinone (Fu & Brock, 1998). The B-C bond lengths (1.56-1.58 Å ) are also comparable to those found in boronic and borinic acids (Hall, 2005).…”

Section: Molecular Geometrysupporting

confidence: 70%

“…In contrast to structure (I), the C()Á Á ÁB interactions in (II) are formed with the -C atom, which provides a very efficient stacking (Table 3). A similar pattern of -stacking contacts occurs in the structure of anthraquinone (Fu & Brock, 1998) and the closer analogue 5,10-dibromo-5,10-dihydroboranthrene (Januszewski et al, 2011).…”

Section: Crystal Structure Of (Ii)mentioning

confidence: 56%

Competition between hydrogen and halogen bonding in the structures of 5,10-dihydroxy-5,10-dihydroboranthrenes

Durka

Luliński

Jarzembska

et al. 2014

Acta Crystallogr Sect B

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X-ray crystallographic and computational studies are reported for a series of boranthrenes, substituted with halogen atoms. The role of competitive hydrogen (O-H...O, O-H...F, C-H...O) and halogen (Cl...Cl, O...Br, F...F) bonding interactions on the molecular arrangement in the crystal structures is discussed. The structural analysis and calculations reveal that the O-H...O hydrogen bond in the unsubstituted derivative 5,10-dihydroxy-5,10-dihydroboranthrene, C12H10B2O2, is of moderate strength (ca -20 kJ mol(-1)), but weaker than that in the related thiophene derivative 4,8-dihydro-4,8-dihydroxy-p-diborino[2,3-b:5,6-b]dithiophene, C8H6B2O2S2 (ca -40 kJ mol(-1)). This is due to shielding of the OH group by the H atoms in the β-position of the boranthrene unit. Structural diversity derived from the flexibility of the O-H...O hydrogen bond facilitates the occurrence of other competitive interactions. For instance, in the 1,6-difluoro derivative, C12H8B2F2O2, the crystal packing results from O-H...F and F...F interactions. In turn, the 1,6-dibromo derivative, C12H8B2Br2O2, is dominated by Br...O halogen-bond interactions. In the most interesting case, the 1,6-dichloro derivative, C12H8B2Cl2O2, molecular disorder leads to the formation of two different supramolecular arrangements co-existing in the crystal lattice, one based on the Cl...Cl and C-H...O bonds, and the other stabilized by O-H...O hydrogen bonds. Calculations performed with density-functional theory (DFT; CRYSTAL09) and PIXEL methodologies show that both lattices are characterized by similar energy values (ca -100 kJ mol(-1)). A mixed arrangement with random or short-range-ordered molecular orientations can also be expected.

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“…Both molecules are stable, and the average bond distances and bond angles are comparable with the crystallographic data. 44 The simulation box was prepared by introducing three monodispersed replicas of the same heptapeptide, with or without the presence of a single small molecule (AQ or AC). The concentration ratio peptide:compound of 3:1 is the minimal choice to have inhibitory effects and complex oligomeric structures.…”

Section: Simulation Protocol and Analysismentioning

confidence: 99%

9,10‐Anthraquinone hinders β‐aggregation: How does a small molecule interfere with Aβ‐peptide amyloid fibrillation?

et al. 2009

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Amyloid aggregation is linked to a number of neurodegenerative syndromes, the most prevalent one being Alzheimer's disease. In this pathology, the b-amyloid peptides (Ab) aggregate into oligomers, protofibrils, and fibrils and eventually into plaques, which constitute the characteristic hallmark of Alzheimer's disease. Several low-molecular-weight compounds able to impair the Ab aggregation process have been recently discovered; yet, a detailed description of their interactions with oligomers and fibrils is hitherto missing. Here, molecular dynamics simulations are used to investigate the influence of two relatively similar tricyclic, planar compounds, that is, 9, 10-anthraquinone (AQ) and anthracene (AC), on the early phase of the aggregation of the Ab heptapeptide segment H 14 QKLVFF 20 , the hydrophobic stretch that promotes the Ab self-assembly. The simulations show that AQ interferes with b-sheet formation more than AC. In particular, AQ intercalates into the b-sheet because polar interactions between the compound and the peptide backbone destabilize the interstrand hydrogen bonds, thereby favoring disorder. The thioflavin T-binding assay indicates that AQ, but not AC, sensibly reduces the amount of aggregated Ab 1-40 peptide. Taken together, the in silico and in vitro results provide evidence that structural perturbations by AQ can remarkably affect ordered oligomerization. Moreover, the simulations shed light at the atomic level on the interactions between AQ and Ab oligomers, providing useful insights for the design of small-molecule inhibitors of aggregation with therapeutic potential in Alzheimer's disease.

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Temperature Dependence of the Rigid-Body Motion of Anthraquinone

Cited by 19 publications

References 18 publications

Structure of a stacked anthraquinone–DNA complex

Structure of a stacked anthraquinone–DNA complex

Competition between hydrogen and halogen bonding in the structures of 5,10-dihydroxy-5,10-dihydroboranthrenes

9,10‐Anthraquinone hinders β‐aggregation: How does a small molecule interfere with Aβ‐peptide amyloid fibrillation?

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