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(a). Absorption spectra of 1-AHAQ (20 mM) in the absence (Curve-1) and in the presence of different calf thymus DNA concentrations (Curve-2-7). pH¼ 7.4, [NaCl]¼ 120 mM, 25 °C. (b). Double reciprocal plot, (A 0 /A-A 0 ) vs. 1/[DNA], of 1-AHAQ-calf thymus DNA interaction; [1-AHAQ] 0 ¼ 20 mM, pH¼ 7.4, [NaCl]¼ 120 mM, 25 °C.
Source publication
The X-ray diffraction and spectroscopic properties of 1-amino-4-hydroxy-9,10-anthraquinone (1-AHAQ), a simple analogue of anthracycline chemotherapeutic drugs were studied by adopting experimental and computational methods. The optimized geometrical parameters obtained from computational methods were compared with the results of X-ray diffraction a...
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... aqueous media containing 2% ethanol at physiological pH (7.4), in the presence of 120 mM NaCl, the absorption spectrum of 1-AHAQ was as shown in Fig. 5a which exhibits an absorption peak at 530 nm. To study the 1-AHAQ-DNA interaction, a set of ex- perimental solutions was prepared consisting of a fixed con- centration of 1-AHAQ ([1-AHAQ] ¼20 mM) and variable con- centrations of ct DNA. The absorbance of such solutions were measured at 530 nm and applied to determine the binding para- ...
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... of ex- perimental solutions was prepared consisting of a fixed con- centration of 1-AHAQ ([1-AHAQ] ¼20 mM) and variable con- centrations of ct DNA. The absorbance of such solutions were measured at 530 nm and applied to determine the binding para- meters. The change in absorption spectra of the compound with increasing amount of DNA is shown in Fig. 5a which clearly in- dicates a hypochromic effect along with a slight bathochromic shift with the increase in concentration of DNA. These shifts were produced as the result of the electronic interaction owing to the intercalation of the compound chromophore into DNA backbone [68][69][70][71]. In order to check whether hypocromism in the ...
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... plot of A 0 /(A-A 0 ) vs. the inverse of the concentration of DNA according to Eq. (2) (Fig. 5b) is a straight line which produced K as (1.09 70.11) Â 10 4 M À 1 ...
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... also evaluated. Fig. 6b shows the binding isotherm of 1-AHAQ with DNA from which the apparent binding constant was determined by using Eq. (8) as (1.20 70.08) Â 10 4 M À 1 . The double reciprocal plot (Fig. 6a) produced the apparent binding constant as (1.56 70.10) Â 10 4 M À 1 . Using the plot of A 0 /(A À A 0 ) against the inverse of [DNA] ( Fig. 5b), K was obtained as (1.09 70.11) Â 10 4 M À 1 (summarized in Table 4). Comparing the values of K, it is clear that three methods for the determination of K correlate excellently. The plot of (ΔA/ΔA m ) vs. the mole ratio of 1-AHAQ to DNA bases [ Fig. S5 (Supporting information)] produced two straight lines intersecting with each other ...
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... (1.56 70.10) Â 10 4 M À 1 . Using the plot of A 0 /(A À A 0 ) against the inverse of [DNA] ( Fig. 5b), K was obtained as (1.09 70.11) Â 10 4 M À 1 (summarized in Table 4). Comparing the values of K, it is clear that three methods for the determination of K correlate excellently. The plot of (ΔA/ΔA m ) vs. the mole ratio of 1-AHAQ to DNA bases [ Fig. S5 (Supporting information)] produced two straight lines intersecting with each other at particular point which actually gives the bind site size or binding stoichiometry (n) in terms of DNA bases bound per molecule of 1-AHAQ [12,[14][15][16][74][75][76][77][78][79]. In the present study 'n' was established as (6.52 70.42) bases, i.e., ...
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... DNA in bases in the experimental solution. It is important to mention here that this method is valid only for those experiments where the free DNA is present in large excess in comparison to that of the compound tested [79]. The present study followed this condition as we mentioned above, and that is the reason why such a double reciprocal plot [ Fig. S5 (Supporting information)] should be useful in our case. Using the method, K was evaluated as (1.50 70.12) Â 10 4 M À 1 which corroborate nicely with the values observed from other methods (Table 4). A com- parison of the present results with an earlier study [81] it can be said that intrinsic and apparent binding constants obtained in ...
Citations
... Taking into account the above, different simpler and cheaper anthraquinones (quinizarin, danthron, purpurin) have been investigated and compared with the known drugs. [6][7][8][9] Surfactants with their unique structure that contains both hydrophilic and hydrophobic moieties in the same molecule can form aggregates (micelles) at a certain concentration (known as critical micelle concentration, CMC) due to a delicate balance between the interactions of polar and non-polar parts. Besides their extensively use in the textile and pharmaceutical industries as solubility enhancers, diluents or emulsifying agents, surfactant micelles can be used in drug delivery systems to increase the solubility and bioavailability of hydrophobic drugs and to protect the drug molecules from adverse effects of the biological environment. ...
Association behavior between quinizarin (1,4-dihydroxy-9,10-anthraquinone, Q), an analogue of the chromophore of anthracycline anticancer drugs and sodium dodecyl sulfate (SDS) micelles in the presence of glucose, NaCl and urea additives was studied using absorption spectroscopy and conductometric techniques. The spectral results indicate an increase of binding constant and partition coefficient values in the presence of glucose and NaCl whereas the addition of urea leads to a decrease of binding strength and quinizarin partitioning into SDS micelles. Thus, the rise of NaCl and glucose concentrations is favorable for the quinizarin distribution into SDS micelles. From electrical conductivity measurements it was found that the critical micelle concentration (CMC) of SDS/quinizarin system decreases by adding NaCl and glucose whereas urea has not influence on the micelization process at the concentrations used in the present study. Since biologically compounds like glucose, NaCl and urea are found in the human body, the attained outcomes can be important in finding of effective drug delivery systems.
... Despite their widespread acceptance in chemotherapy, their use is frequently questioned due to the associated cardiotoxicity and high cost, especially for those from the economically disadvantaged parts of society. As a result, there are efforts being made globally to identify cheaper alternatives that are less cardiotoxic [52][53][54][55][56][57]. These are either less expensive anthracycline derivatives or their less complex analogues [58][59][60][61][62][63][64]. ...
... In MDA-MB-231 breast adenocarcinoma cells, it causes apoptosis, whereas it has no effect on HBL-100 normal breast epithelial cells. The molecule's function as a possible anti-tumor agent may be influenced by its electrochemical aspects, structural features, and propensity to interact with DNA [53]. Electrochemical analysis revealed that 1-amino-4-hydroxy-9,10-anthraquinone (QH) was significantly different from ...
Anthraquinones constitute an important class of compounds with wide applications. The solubility of derivatives at 298.15 K was discussed in ethanol–water solution and at atmospheric pressure, the solubility of 1-amino-4-hydroxy-9,10-anthraquinone (AHAQ) in binary solvents (ethanol–water combinations) was determined. Colour strength and fastening properties depend upon the kind and position of a hydrophobic group connected to the phenoxy ring of Anthraquinone moiety. There is a continuing interest in the creation of novel anthraquinone derivatives with biological activities since they have demonstrated potential for treating multiple sclerosis. For this purpose, by utilizing voltammetric and absorption studies, interactions of various derivatives with calf thymus DNA (ct-DNA) and the cationic surfactant cetyltrimethylammoniumbromide (CTAB) were examined. Here prominent Hydrophobic interaction and electron transfer resulting in binding to CTAB micelles were observed. The polarity index of the media was assessed and associated with the electrochemical parameters. The medicinal behaviour of Anthraquinone derivatives was a result of electron transfer reactions with DNA. UV–Visible and fluorescence properties were due to the transitions between n* and π* orbitals. Large absorption band with low dichroic ratio was characteristic of various derivatives of Anthraquinone. Presence of –NH group proves various derivatives remarkable calorimetric and anionic sensors.
Graphical Abstract
... Animals administered of chrysophanol had adverse reactions such as bowel sounds, nausea, vomiting, abdominal pain and diarrhea. Thus, structural modifications of chrysophanol have been utilized to improve therapeutic efficacy and alleviate its side effect (Shrestha et al., 2014;Mondal et al., 2015). ...
Acute liver failure (ALF) is an unfavorable condition characterized by the rapid loss of liver function and high mortality. Chrysophanol-8-O-glucoside (CPOG) is an anthraquinone derivative isolated from rhubarb. This study aims to evaluate the protective effect of CPOG on lipopolysaccharide (LPS)/D-GalN-induced ALF and its underlying mechanisms. LPS/D-GalN-induced mice ALF model and LPS treatment model in RAW 264.7 and LX2 cells were established. It was found that CPOG ameliorated LPS/D-GalN-induced liver injury and improved mortality as indicated by Hematoxylin-eosin (H&E) staining. Molecularly, qPCR and ELISA results showed that CPOG alleviated LPS/D-GalN-induced release of alanine aminotransferase and aspartate transaminase and the secretion of TNF-α and IL-1β in vivo. LPS/D-GalN-induced intracellular ROS production was also attenuated by CPOG in liver tissue. Further, CPOG attenuated ROS generation and inhibited the expression of p-IκB and p-p65 as well as the expression of TNF-α and IL-1β stimulated by LPS in RAW 264.7 cells. In addition, CPOG alleviated LPS-induced up-regulation of LC3B, p62, ATG5 and Beclin1 by attenuating ROS production and inhibiting MAPK signaling in LX2 cells. Taken together, our data indicated that the CPOG protected against LPS/D-GalN-induced ALF by inhibiting oxidative stress, inflammation response and autophagy. These findings suggest that CPOG could be potential drug for the treatment of ALF in clinic.
... The therapeutic efficacy and biological activity of any chemical entity depend on its structure and arrangement of functional groups, so as HAQ whose therapeutic properties depends upon multiple groups present on its ring (Mondal et al. 2015), transduction of the spatial orientation (Shrestha et al. 2014) and formation of intermolecular hydrogen bonds along with the configuration, size, and type of the substitute. Teng et al. (2007) reported that chrysophanol accumulation was much greater in intestinal Caco-2 cells than that of emodin which was attributed to the higher hydroxyl group's presence in chrysophanol. ...
Anthraquinones (AQ), unveiling large structural diversity, among polyketides demonstrate a wide range of applications. The hydroxy anthraquinones (HAQ), a group of anthraquinone derivatives, are secondary metabolites produced by bacteria and eukaryotes. Plant-based HAQ are well-studied unlike bacterial HAQ and applied as herbal medicine for centuries. Bacteria are known to synthesize a wide variety of structurally diversified HAQ through polyketide pathways using polyketide synthases (I, II & III) principally through polyketide synthase-II. The actinobacteria especially the genus Streptomyces and Micromonospora represent a rich source of HAQ, however novel HAQ are reported from the rare actinobacteria genera (Salinospora, Actinoplanes, Amycoloptosis, Verrucosispora, Xenorhabdus, and Photorhabdus. Though several reviews are available on AQ produced by plants and fungi, however none on bacterial AQ. The current review focused on sources of bacterial HAQ and their structural diversity and biological activities along with toxicity and side effects.
... The therapeutic efficacy and biological activity of any chemical entity depend on its structure and arrangement of functional groups, so as HAQ whose therapeutic properties depends upon multiple groups present on its ring (Mondal et al. 2015), transduction of the spatial orientation (Shrestha et al. 2014) and formation of intermolecular hydrogen bonds along with the configuration, size, and type of the substitute. Teng et al. (2007) reported that chrysophanol accumulation was much greater in intestinal Caco-2 cells than that of emodin which was attributed to the higher hydroxyl group's presence in chrysophanol. ...
Anthraquinones (AQ), unveiling large structural diversity, among polyketides demonstrate a wide range of applications. The hydroxy anthraquinones (HAQ), a group of anthraquinone derivatives , are secondary metabolites produced by bacteria and eukar-yotes. Plant-based HAQ are well-studied unlike bacterial HAQ and applied as herbal medicine for centuries. Bacteria are known to synthesize a wide variety of structurally diversified HAQ through polyketide pathways using polyketide synthases (I, II & III) principally through polyketide synthase-II. The actinobacteria especially the genus Streptomyces and Micromonospora represent a rich source of HAQ, however novel HAQ are reported from the rare actinobacteria genera (Salinospora, Actinoplanes, Amycoloptosis, Verrucosispora, Xenorhabdus, and Photorhabdus. Though several reviews are available on AQ produced by plants and fungi, however none on bacterial AQ. The current review focused on sources of bacterial HAQ and their structural diversity and biological activities along with toxicity and side effects. ARTICLE HISTORY
... The FTIR spectrum for QH ( Figure S2, SI) shows a peak at 3431 cm −1 , which is due to N−H bond stretching, while that at 3300 cm −1 is due to stretching of O−H bonds. 6 The O−H stretching is modified significantly in the complex ( Figure S3, SI), indicating an involvement of the −OH group during complex formation. Since there is deprotonation of −OH during complex formation, the molecule ceases to show intramolecular hydrogen bonding identified in QH. ...
... In the IR spectrum of CoQ 3 ( Figure S3, SI), peaks at 1625, 1586, and 1537 cm −1 are attributed to stretching due to free carbonyl and CC or a combination of both, respectively. In an earlier study, 6 we showed that peaks obtained in the region 1464−1031 cm −1 in the IR spectrum of the ligand (QH) may be attributed to combinations of O−H, N−H, and C−H bending modes. Natures of the peaks in this region are somewhat different in the complex. ...
... UV−vis Spectroscopy of CoQ 3 . The absorption spectrum of QH ( Figure 4a) in 30% ethanol 6,7 shows four absorption bands (at 250, 290, 530, and 565 nm) due to π−π* and n−π* transitions of its various tautomeric forms in rapid equilibrium in aqueous solution. 6,7,49 From the UV−vis spectrum of CoQ 3 (Figure 4b), it is clear that the absorption peaks at 250, 290, 530, and 565 nm remain almost unaltered, which indicate that the electronic absorption spectrum of CoQ 3 depends weakly on the nature of the metal and is primarily defined by the ligand (QH). ...
A Co(III) complex of 1-amino-4-hydroxy-9,10-anthraquinone (QH) (Scheme-1) having the molecular formula CoQ3 (Scheme-2) was prepared and characterized by elemental analysis, FTIR spectroscopy, UV–vis spectroscopy, fluorescence spectroscopy, and mass spectrometry. In the absence of a single crystal, the energy-optimized molecular structure of CoQ3 was determined by employing computational methods that was validated using spectroscopic evidences, elemental analysis, and mass spectrometry data. The electrochemical properties of the complex were analyzed using cyclic voltammetry and indicate a substantial modification of the electrochemical properties of the parent amino-hydroxy-9,10-anthraquinone. CoQ3 was thereafter tested on MCF-7 human breast cancer cells. The IC50 value for a 24 h incubation was found to be (95 ± 0.05) μg/mL. The study showed that such cancer cells underwent both early and late apoptosis following the interaction with CoQ3.
... The mathematical correlation of experimental data of pharmaceutical compounds is important for practical predictions/validations [20,33,39,40]. As a result, the measured solubility values of CNZ were predicted using the modified "Apelblat, van't Hoff, Yalkowsky-Roseman, Jouyban-Acree, and Jouyban-Acree-van't Hoff models" [18][19][20][24][25][26][27]. ...
Between 293.2 and 313.2 K and at 0.1 MPa, the solubility of the weak base, cinnarizine (CNZ) (3), in various {Transcutol-P (TP) (1) + water (2)} combinations is reported. The Hansen solubility parameters (HSP) of CNZ and various {(TP) (1) + water (2)} mixtures free of CNZ were also predicted using HSPiP software. Five distinct cosolvency-based mathematical models were used to link the experimentally determined solubility data of CNZ. The solubility of CNZ in mole fraction was increased with elevated temperature and TP mass fraction in {(TP) (1) + water (2)} combinations. The maximum solubility of CNZ in mole fraction was achieved in neat TP (5.83 × 10-2 at 313.2 K) followed by the minimum in neat water (3.91 × 10-8 at 293.2 K). The values of mean percent deviation (MPD) were estimated as 2.27%, 5.15%, 27.76%, 1.24% and 1.52% for the "Apelblat, van't Hoff, Yalkowsky-Roseman, Jouyban-Acree, and Jouyban-Acree-van't Hoff models", respectively, indicating good correlations. The HSP value of CNZ was closed with that of neat TP, suggesting the maximum solubilization of CNZ in TP compared with neat water and other aqueous mixtures of TP and water. The outcomes of the apparent thermodynamic analysis revealed that CNZ dissolution was endothermic and entropy-driven in all of the {(TP) (1) + water (2)} systems investigated. For {(TP) (1) + water (2)} mixtures, the enthalpy-driven mechanism was determined to be the driven mechanism for CNZ solvation. TP has great potential for solubilizing the weak base, CNZ, in water, as demonstrated by these results.
... Chr, also known as 1,8-dihydroxy-3-methyl-anthraquinone, is a representative mono-nuclear compound with methyl substitution that plays a significant role in natural anthraquinone compounds. In recent years, various types of structural modifications have been utilized to improve therapeutic efficacy and biological activity, such as the introduction of multiple groups [81], transduction of the spatial orientation [82], and formation of intermolecular hydrogen bonds. Simultaneously, the configuration, size and type of the substitute could produce structural modifications. ...
As a universal Chinese medicine, Rhei Radix et Rhizoma was used for centuries in different fields including pharmaceutical, health care and cosmetics. Chrysophanol (Chr) is one of the most important anthraquinone components isolated from plants of the Rheum genus. Current reports show that in Rheum officinale, Chr is the most abundant free anthraquinone compound [1] and exerts a number of beneficial effects, such as anti-inflammation, anti-cancer, and anti-depressive effects and offers neuroprotection. We collected information about Chr from the Internet databases PubMed, Web of Science, Europe PMC and CNKI with a combination of keywords including "Chr", "Pharmacology", and "Pharmacokinetics". All data about this ingredient in this review were extracted from articles published before September 2019. Based on the literature found, we concluded that (1) Chr exhibited potential anti-inflammation, anti-cardiovascular disease (CVD)and anti-cancer activities by regulating signaling pathway transduction (NF-κB, MAPK, PI3K/Akt, etc.); (2) compared with free Chr, pharmacokinetic studies revealed that other forms of Chr, such as nanoparticle-based and liposome-based Chr, showed high bioavailability. Nevertheless, we also found that the understanding of the exact differences in the regulation of multiple molecular signaling pathways is in a preliminary stage and needs to be clarified. Moreover, further studies are required to determine the apoptotic mechanism of Chr in cancer cells. Finally, we found that (3) structure modification studies demonstrated potential relationships between structure and drug activity. The purpose of this review is to summarize the pharmacological activities, intracorporal processes and structure-activity relationships of Chr and to provide an up-to-date reference for further research and clinical applications.
... This might be related to the dissolution of the drug in the cell medium and transportation into the cell. In 2015, Mondal et al. used 1-amino-4-hydroxy-9,10-anthraquinone on MDA-MB-231 breast adenocarcinoma cells; they reported 50% inhibitory rates of this molecule as 200 µM for 24 h of incubation and 140 µM for 48 h of incubation [17]. In another study, 3-isobutylhexahydropyrrolo [1,2-a]pyrazine-1,4-dione (PPDHMP), which was extracted from a new marine bacterium called Staphylococcus sp. ...
... These types of quinone derivatives can be incorporated into the structure of polypeptides or proteins, giving the opportunity to track physiological processes. In addition, due to their antineoplastic properties and an ability to intercalate into DNA, they may act as chemotherapeutic agents [14][15][16][17][18][19]. ...
Six novel amino acid chromophores were synthesized and their spectroscopic, acid-base, and electrochemical
properties are discussed in this work. In studied compounds, selected amino acid residues (L-Aspartic acid, LGlutamic
acid, L-Glutamine, L-Histidine, L-Lysine, L-Arginine) are attached to the 1-(piperazine) 9,10-anthraquinone
skeleton via the amide bond between the carboxyl group of amino acid and nitrogen atomof the piperazine
ring. All derivatives have been characterized using a variety of spectroscopic techniques (mass spectrometry,
1HNMR, UV–Vis, IR spectroscopy), acid-base (electrochemical and UV–Vis) titrations, and cyclic voltammetry
methods. Basing on observed experimental effects, supported by quantum chemical simulations, the structureproperties
links were established. They are indicative of the specific interactions within and/or in-between
amino acid side groups,which are prone to formboth, intra- and intermolecular hydrogen bonds aswell as electrostatic
interactions with the anthraquinone system.
