Metal Complexes with 1,5- and 1,8-Dihydroxy-9,10-Anthraquinones: Electronic Absorption Spectra and Structure of Ligands

Fain, V. Ya.; Зайцев, Б. Е.; Ryabov, M. A.

doi:10.1023/b:ruco.0000026007.04814.ad

Cited by 8 publications

(3 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The types of metals used can also have an effect on the color of the complexes they form with alizarin, as well as on their thermal and chemical stability. Complexes of alizarin with Al(III), Cr(III), Ni(II), Cu(II), Zn(II), Cd(II), and Fe(III)) are associated with a red-shift of the visible band with respect to the isolated dye [9,31,32]. Both environmental effects are present and influence madder lake color changes.…”

Section: Resultsmentioning

confidence: 99%

Characteristics of Hybrid Pigments Made from Alizarin Dye on a Mixed Oxide Host

et al. 2019

View full text Add to dashboard Cite

This paper describes the fabrication of a new hybrid pigment made from 1,2-dihydroxyanthraquinone (alizarin) on a mixed oxide host (aluminum-magnesium hydroxycarbonate, LH). Various tools were applied to better understand the interactions between the organic (alizarin) and inorganic (LH) components, including ion mass spectroscopy (TOF-SIMS), 27-Aluminm solid-state nuclear magnetic resonance (NMR) spectroscopy, X-ray diffraction (XRD), and thermogravimetric analysis (TGA). TOF-SIMS showed that modification of the LH had been successful and revealed the presence of characteristic ions C14H7O4Mg+ and C14H6O5Al−, suggesting interactions between the organic chromophore and both metal ions present in the mixed oxide host. Interactions were also observed between Al3+ ions and Alizarin molecules in 27Al NMR spectra, with a chemical shift detected in the case of the modified LH matrix. Any changes in color following reactions with Mg2+ and Al3+ ions were observed. Some of the physicochemical properties of alizarin, such as resistance to dissolution and color stability at elevated temperatures, were improved in comparison to the pure dye. This effect can be attributed to strong dye-LH interactions and the effective transformation of alizarin into an insoluble form. Moreover, the pigments exhibited higher thermal resistance and greater color stability in comparison to commercially available alizarin lakes (Alizarin Crimson).

show abstract

Section: Resultsmentioning

confidence: 99%

Characteristics of Hybrid Pigments Made from Alizarin Dye on a Mixed Oxide Host

et al. 2019

View full text Add to dashboard Cite

show abstract

“…The presence of substituents in position 1 and 4 induces a significant bathochromic shift, intensifying the color more significantly than the substituents in the 1,5 and 1,8 positions. Thus, with an alcoholic solution of magnesium acetate, 1,2-dioxyderivative is colored in violet; 1,4-dioxyderivative in purple; and 1,8-dioxyderivative in red-orange [ 28 , 29 , 30 ]. Therefore, fungal anthraquinones range from pale yellow to dark red or brown colors, through to violet.…”

Section: Anthraquinones From Marine-derived Fungimentioning

confidence: 99%

Anthraquinones and Derivatives from Marine-Derived Fungi: Structural Diversity and Selected Biological Activities

et al. 2016

View full text Add to dashboard Cite

Anthraquinones and their derivatives constitute a large group of quinoid compounds with about 700 molecules described. They are widespread in fungi and their chemical diversity and biological activities recently attracted attention of industries in such fields as pharmaceuticals, clothes dyeing, and food colorants. Their positive and/or negative effect(s) due to the 9,10-anthracenedione structure and its substituents are still not clearly understood and their potential roles or effects on human health are today strongly discussed among scientists. As marine microorganisms recently appeared as producers of an astonishing variety of structurally unique secondary metabolites, they may represent a promising resource for identifying new candidates for therapeutic drugs or daily additives. Within this review, we investigate the present knowledge about the anthraquinones and derivatives listed to date from marine-derived filamentous fungi′s productions. This overview highlights the molecules which have been identified in microorganisms for the first time. The structures and colors of the anthraquinoid compounds come along with the known roles of some molecules in the life of the organisms. Some specific biological activities are also described. This may help to open doors towards innovative natural substances.

show abstract

“…[37] The chelation process of these hydroxyanthraquinones usually evolves via their tautomeric anthraquinoid structures. [38] The formation of a wide variety of metal complexes has been reported for quinizarin and anthrarufin, [39] while alizarin exhibiting linkage isomerism, acts as a chelate via the 1,2-or the 1,9-oxygen atoms and forms complexes with Ru, Cu, Ni, Hg, and a variety of transition metals. [40,41] …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopy and in vitro Cytotoxicity of New Hydroxyanthraquinonato Triorganotin Compounds

Valla

Bakola‐Christianopoulou

Kojić

et al. 2007

Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-

View full text Add to dashboard Cite

We will present herein data on the synthesis, structural investigation and in vitro antitumor activity of new triorganotin compounds of the general type (R 3 Sn) 2 Q, where R 5 Bu, Ph, Bz, Q 1 5 1,4-dihydroxy-9,10-anthracenedione (quinizarin), Q 2 5 1,5-dihydroxy-9,10-anthracenedione (anthrarufin), Q 3 5 2,3-dihydro-9,10-dihydroxy-1,4-anthracenedione (leucoquinizarin) and R 3 SnQ 4 where Q 4 5 1,2-dihydroxy-9,10-anthracenedione (alizarin). The compounds were synthesized by refluxing the organotin hydroxide with the parent quinone and were characterized by IR, 1 H-NMR and thermal measurements. The spectroscopic analysis of the new triorganotins, provides evidence on the formation of a monodentate Sn-O bond for quinizarin, anthrarufin and leucoquinizarin, which are coordinated to Sn(IV) central atom via the phenolic oxygen donor atoms, with the R-substituents of the organotin moiety completing the tetrahedral coordination environment. On the contrary, organotin alizarinates form a sixmembered chelate ring, which stabilizes the Sn central atom in a five-coordinated environment exhibiting distorted trigonal bipyramidal geometry. The ligand is coordinated to Sn (IV) via the quinoidal oxygen and its neighbouring phenolic one. The new compounds were tested for their cytotoxicity against human tumor and normal cell lines and the results are reported.

show abstract

Metal Complexes with 1,5- and 1,8-Dihydroxy-9,10-Anthraquinones: Electronic Absorption Spectra and Structure of Ligands

Cited by 8 publications

References 5 publications

Characteristics of Hybrid Pigments Made from Alizarin Dye on a Mixed Oxide Host

Characteristics of Hybrid Pigments Made from Alizarin Dye on a Mixed Oxide Host

Anthraquinones and Derivatives from Marine-Derived Fungi: Structural Diversity and Selected Biological Activities

Synthesis, Spectroscopy and in vitro Cytotoxicity of New Hydroxyanthraquinonato Triorganotin Compounds

Contact Info

Product

Resources

About