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At least 19 recordsLinked to original sources
PubMed1990

Design and applications of biomimetic anthraquinone dyes. III. Anthraquinone-immobilised C.I. reactive blue 2 analogues and their interaction with horse liver alcohol dehydrogenase and other adenine nucleotide-binding proteins.

C.I. Reactive Blue 2 analogues were bonded onto an agarose support matrix by a novel method which entailed immobilisation by the anthraquinone ring 1-amino group as opposed to the usual triazine ring coupling methods. Dyes with spacer arms attached to the anthraquinone ring 1-amino group were synthesised by reacting methoxytriazine analogues of C.I. Reactive Blue 2 with chloroacetyl chloride and ethylenediamine. Unlike the blue parent dyes, all C.I. Reactive Blue 2 analogues with derivatised anthraquinone ring 1-amino groups were of a characteristic red colour. This change of chromaticity was entirely expected since the anthraquinone ring 1-amino group is an important component of the C.I. Reactive Blue 2 chromophore. Chromatographic studies indicated that, in comparison to adsorbents comprising triazine ring-immobilised dyes, adsorbents formed from C.I. Reactive Blue 2 analogues immobilised by the anthraquinone ring were better suited to the isolation of horse liver alcohol dehydrogenase and other adenine nucleotide-requiring enzymes. Similarities between C.I. Reactive Blue 2 analogues immobilised by the anthraquinone ring and N6-(6-aminohexyl)adenine nucleotide derivatives could be identified which may account for these observations. These studies confirm that highly effective affinity ligands based on synthetic textile dyes can be designed in a rational manner.

Adenine Nucleotides↗
PubMed1991

In vitro virucidal activity of selected anthraquinones and anthraquinone derivatives.

Anthraquinones and anthraquinone derivatives were characterized for their antiviral and virucidal activities against viruses representing several taxonomic groups. One of these compounds, hypericin, had activity against vesicular stomatitis virus, herpes simplex virus types 1 and 2, parainfluenza virus, and vaccinia virus (from 0.5 to 3.8 log10 reductions in infectivity) at concentrations of less than 1 microgram/ml as determined by a direct pre-infection incubation assay. Human rhinovirus was not sensitive to hypericin at concentrations up to 10 micrograms/ml. Addition of small amounts of Tween-80 to solutions containing hypericin enhanced, by up to 2.6 log10, hypericin's virucidal activity. Anthraquinones and anthraquinone derivatives with the hydroxyl and alkyl substitution pattern of emodin (i.e. emodin, emodin anthrone, emodin bianthrone and hypericin) were active against the enveloped viruses tested. The following general pattern of activity was found: hypericin greater than emodin bianthrone greater than emodin anthrone greater than emodin. Chrysophanic acid, aloe-emodin, and sennosides A and B did not possess activity against any of the viruses tested.

Animals↗
PubMed1979

Mutagenicity of anthraquinone and benzanthrone derivatives in the Salmonella/microsome test: activation of anthraquinone glycosides by enzymic extracts of rat cecal bacteria.

Approximately 70 anthraquinones and 20 benzanthrones were assayed for mutagenicity in the Salmonella/microsome test, employing 5 tester strains and Aroclor 1254 induced rat-liver microsomes. About one-third of the anthraquinones were frameshift mutagens, particularly phenolic and nitro anthraquinones. The most potent mutagens detected were of plant origin. Lucidin (1,3-dihydroxy-2-hydroxymethylanthraquinone) and its 2-ethyl ether gave values of 70 and 82 revertants per nmol, respectively, with strain TA100 (and microsomes in the case of the ether). A number of glycosides of mutagenic hydroxyanthraquinones were found to be nonmutagenic in the standard assay procedure, but could be activated by incorporation of cell-free sonic extracts of rat cecal bacteria, e.g., alizarin-2-O-beta-D-glycoside, emodin-1 (8)-monoglucoside and lucidin-3-O-primveroside. Over one-third of the benzanthrones tested were frameshift mutagens for Salmonella; the most potent response of 64 revertants/nmol was obtained with 3-p-toluidinobenzanthrone and microsomal activation in strain TA98.

Anthraquinones↗
PubMed1995

Anti-human cytomegalovirus activity and toxicity of sulfonated anthraquinones and anthraquinone derivatives.

Sulfonated anthraquinones and other anthraquinone derivatives were evaluated for anti-human cytomegalovirus (HCMV) activity, cytotoxicity and genotoxicity. Acid blues 40 and 129, acid black 48, alizarin violet R and reactive blue 2 were the most active compounds having selective indices of greater than 30 and EC50 values of 4-30 microM. When tested against a clinical isolate, the 4 compounds were 2- to 5-fold less active. The antiviral activity was distinctly separate from the virucidal activity (> 1000 microM). The compounds were weakly toxic to either log phase or stationary cells in most of the following cytotoxicity assays: neutral red uptake assay, lactic acid dehydrogenase assay, trypan blue exclusion assay and radiolabeled macromolecular precursor uptake assays. Using a genotoxicity assay, the comet assay, only reactive blue 2 and acid black 48 were found to cause DNA strand breakage. This occurred at concentrations of 30 and 170 microM, respectively. These results suggest that these compounds could be a prototype for synthesizing even more effective HCMV-inhibitory anthraquinone derivatives.

Anthraquinones↗
PubMed1982

Mutagenicity of anthraquinone and hydroxylated anthraquinones in the Ames/Salmonella microsome system.

The mutagenicity of anthracene, anthraquinone, and four structurally similar compounds of each was evaluated in the Ames/Salmonella microsome assay. Anthraquinone was shown to be mutagenic for strains TA1537, TA1538, and TA98 in the absence of rat liver homogenate. The four anthraquinone derivatives tested were mutagenic for TA1537 exclusively. None of the anthracenes exhibited mutagenic activity.

Anthracenes↗
PubMed1992

The coordination of copper(II) to 1-hydroxy-4-(glycyl-histidyl-lysine)-anthraquinone; a synthetic model of anthraquinone anti-cancer drugs.

Results are reported of a pH-metric and spectroscopic (CD and ESR) study of the complexes formed between the pseudo-peptide 1-hydroxy-4-(Gly-His-Lys)-anthraquinone (Q-GHK) since, when complexed to copper ions, Q-GHK has been shown to be very effective in promoting the formation of free radicals and inducing DNA cleavage. Q-GHK forms very stable complexes with copper, the major species being bonded to three nitrogen donors in the coordination plane: an imidazole-N of the His residue and the peptide nitrogens of the Gly and His residues. This species is probably stabilized through bonding of the fourth planar coordination site of Cu(II) to the 9-anthraquinone oxygen. At high Q-GHK:copper ratios a second Q-GHK molecule is coordinated through its imidazole-N donor.

Anthraquinones↗
PubMed1992

Evaluation of the antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cytomegalovirus.

A number of anthraquinones, anthrones and anthraquinone derivatives were evaluated for antiviral activity against human cytomegalovirus (HCMV) as well as for cytotoxicity. Of those compounds evaluated, quinalizarin, emodin, rhein, hypericin, protohypericin, alizarin, emodin bianthrone and emodin anthrone showed antiviral activity against a normal laboratory HCMV strain, AD-169. When tested against a ganciclovir-resistant strain of HCMV, the EC50 values for quinalizarin, rhein and alizarin were superior to the values obtained for the AD-169 strain of HCMV. These results suggest that these compounds will be useful as prototypes for synthesizing a class of anti-HCMV drugs that are effective against ganciclovir-sensitive and -resistant strains of HCMV.

Anthracenes↗
PubMed1993

A theoretical study of the mechanism of oxygen binding by model anthraquinones. Part II. Quantum-mechanical studies of the energetics of oxygen binding to model anthraquinones.

Anthracycline derivatives, which constitute an important class of antitumor drugs, exhibit undesirable cardiotoxicity owing to their mediation in the process of oxygen reduction to the superoxide anion radical. Earlier work showed that this mediation could be facilitated by the formation of complexes with the 1 delta g oxygen molecule prior to reduction. In this paper, we investigate the energetics of the possible peroxides formed by a series of model anthraquinones: 1,4-dihydroxyl- (quinizarin), 1,8-dihydroxyl-, 1-hydroxy-8-methoxy-, 1,8-dimethoxy-, 1,4,5-trimethoxy- and 1,4-dihydroxy-5-methoxy-9,10-anthracenedione, as well as of daunorubicin and demethoxydaunorubicin, by semi-empirical quantum-mechanical MNDO and PM3 methods, and limited STO-3G ab initio calculations. It was found that the oxygen-binding site is determined by three factors: the high electron density and high HOMO coefficients on the carbon atoms to which oxygen binds, the minimum loss of conjugation within the anthraquinone moiety on oxygen binding and the minimum number of bonds to other heavy atoms of the oxygen-binding carbons (the steric effect). For different molecules, the energy of the most stable oxygen complex is the greatest for compounds with the lowest ionization potential. On the basis of this and our earlier studies, it was concluded that the anthracycline derivatives with reduced ability to bind oxygen and, therefore, reduced cardiotoxicity, should possess a high symmetry of II-electron density distribution, a high ionization potential and have all of the oxygen-binding sites condensed to other rings or substituted by bulky groups.

Anthraquinones↗
PubMed1995

Molecular modeling of singlet-oxygen binding to anthraquinones in relation to the peroxidating activity of antitumor anthraquinone drugs.

Anthraquinone derivatives are important anti-cancer drugs possessing, however, undesirable peroxidating and, in consequence, cardiotoxic properties. This results from the mediation by these compounds of the one-electron reduction processes of the oxygen molecule, which produces the highly toxic superoxide anion radical and other active oxygen species. This article summarizes the results of our studies on the molecular aspects of the mechanism of anthraquinone-mediated peroxidation which were carried out using enzymatic-assay, electrochemical, and quantum-mechanical methods.

Anthraquinones↗
PubMed2005

Drastic difference in lifetimes of the charge-separated state of the formanilide-anthraquinone dyad versus the ferrocene-formanilide-anthraquinone triad and their photoelectrochemical properties of the composite films with fullerene clusters.

A long-lived charge-separated (CS) state, which can be observed even at 900 mus after laser excitation, has been attained in the formanilide-anthraquinone dyad (FA-AQ) in dimethyl sulfoxide, whereas the CS lifetime is shortened significantly to 20 ps in the ferrocene-formanilide-anthraquinone triad (Fc-FA-AQ). Such a drastic decrease in the CS lifetime by the addition of a ferrocene moiety to the FA-AQ dyad is ascribed to a decrease in the driving force of back electron transfer and an increase in the reorganization energy of electron transfer despite the longer charge-separation distance. The FA-AQ dyad and the Fc-FA-AQ triad have been employed as components of photovoltaic cells, where composite molecular nanoclusters of the FA-AQ dyad or the Fc-FA-AQ triad with fullerene (C60) are assembled onto a SnO2 electrode using an electrophoretic method. The composite films of the Fc-FA-AQ triad exhibit 10 times smaller values of an incident photon-to-photocurrent efficiency (IPCE) as compared with those of the FA-AQ dyad in accordance with a drastic decrease of the CS lifetime by addition of a ferrocene moiety to the FA-AQ dyad.

Journal Article↗
PubMed1994

Identification of adducts formed by reaction of purine bases with a mutagenic anthraquinone, lucidin: mechanism of mutagenicity by anthraquinones occurring in rubiaceae plants.

A mutagenic anthraquinone, lucidin (1), occurring in Rubiaceae plants, reacted with nucleic bases under physiological conditions to form adducts. The order of the reactivity is as follows: adenine > guanine >> pyrimidine bases approximately 0. By spectroscopic analyses, the isolated purine base adducts were identified as condensed reactants at the benzylic position of 1 with a nitrogen atom of a purine base. The results indicate a strong possibility of the formation of an exomethylenic compound as an electrophile intermediate.

Anthraquinones↗
PubMed2006

Ultrafast intersystem crossing in 9,10-anthraquinones and intramolecular charge separation in an anthraquinone-based dyad.

Femtosecond transient absorption spectroscopy was employed to determine quantitatively the ultrafast S1-T1 intersystem crossing in a 2-substituted 9,10-anthraquinone derivative (3), kisc = 2.5 x 10(12) s-1. Notwithstanding this rapid process, photoexcitation of dyad 1 is followed by competition between intersystem crossing and intramolecular charge separation, the latter leading to a short-lived (2 ps) singlet charge-transfer (CT) state. The local triplet state itself undergoes slower charge separation to populate a relatively long-lived (130 ns) triplet CT state. An earlier report about the formation of an extremely long-lived CT state (> 900 micros) in 1 was found to be erroneous and was related to the sacrificial photo-oxidation of the dimethylsulfoxide solvent used in that study. Finally, some important criteria have been formulated for future experimental validation of "unusually long-lived" CT states.

Journal Article↗