- Synthesis of water-soluble 9,10-anthraquinone analogues with potent cyanobactericidal activity toward the musty-odor cyanobacterium Oscillatoria perornata
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A series of water-soluble 9,10-anthraquinone analogues were prepared and evaluated for their selective toxicity toward Oscillatoria perornata, which grows in catfish production ponds and causes musty off-flavor in channel catfish (Ictalurus punctatus). Water-soluble mono- and dicationic salts were prepared by conjugating various small amines directly or through a methylene or ethylene bridge to the 9,10-anthraquinone nucleus. One of the dicationic salts, 2-[N-(1′-methyl-4′-N,N-diethylaminobutyl) aminometyl]anthraquinone diphosphate, exhibited very high water solubility and potent selective toxicity toward O. perornata. However, the tendency of this compound to potentially bind to suspended sediments may be the reason for its limitations in controlling O. perornata in catfish production ponds. The monocationic salt, 2-[N-(1′-methylethyl)]aminomethyl]anthraquinone monophosphate, showed good solubility and high selective toxicity toward O. perornata. Neutral water-soluble analogues prepared by conjugating terta- or pentaethylene glycol directly or by a methylene bridge to the 9,10-anthraquinone nucleus had less activity than the parent compound.
- Nanayakkara, N. P. Dhammika,Schrader, Kevin K.
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- The design and synthesis of a photo-controlled, peptide-based potential drug carrier
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Our focus in this study is on the design and synthesis of a light-responsive peptide-based nanocarrier in order to develop effective and biocompatible drug delivery systems. The synthesized nanocarrier is basically composed of peptide amphiphiles comprising a micelle forming a Pro-Pro-Pro-Lys-Lys-Lys peptide sequence with an attached anthracene fluorophore. Anthracene containing an inner core of the micelle can serve as a storage site for poorly water-soluble drugs. Moreover, anthracenes that come in close proximity with the formation of micellar structures can undergo photodimerization upon irradiation at 365 nm, which disrupts the micelle structures formed by the self-assembly of the peptide amphiphiles. Therefore, if a drug is encapsulated within the hydrophobic core of this peptidic carrier system, its release can be induced by the controlled exposure of the anthracene moiety to UV light.
- Parlak Khalily, Melek,?z?ubuk?u, Salih
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- High-sensitivity HPLC quantification of nonfluorescent but photolabile analyte through photoreversion in fluorescence detector
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Ultrahigh sensitivity chiral HPLC analysis of nonfluorescent cyclodimers of 2-anthracenecarboxylic acid (AC) was achieved with much improved accuracy and reproducibility through a nonconventional on-detector photoreversion/re- excitation/detection mechanism. Excitation of cyclodimers at 254 nm in the detector cuvette caused photoreversion to AC, in situ excitation of which led to strong fluorescence at longer λ. The sensitivity was enhanced by a factor of ca. 2000 compared to usual UV detection. Copyright
- Nishijima, Masaki,Wada, Takehiko,Nagamori, Koushi,Inoue, Yoshihisa
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- Preparation and Evaluation of 2-Substituted Anthraquinones Based on the Anthracyclines
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Anthraquinones substituted at the 2 position with a basic side chain were prepared, and their binding to DNA was evaluated.All compounds showed an intercalative mode of binding to DNA; 1,4-dihydroxy derivatives bound more strongly than 1-hydroxy or nonhydroxylated compounds.Greatest DNA-binding activity was found where there were five atoms between the anthraquinone ring and the basic nitrogen.
- Bennett, Stephen,Sharples, Derek,Brown, Jeffrey R.
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- Selective photocytotoxicity of anthrols on cancer stem-like cells: The effect of quinone methides or reactive oxygen species
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Cancer stem cells (CSCs) are a subpopulation of cancer cells that share properties of embryonic stem cells like pluripotency and self-renewal and show increased resistance to chemo- and radiotherapy. Targeting CSC, rather than cancer cells in general, is a novel and promising strategy for cancer treatment. Novel therapeutic approaches, such as photodynamic therapy (PDT) have been investigated. A promising group of phototherapeutic agents are reactive intermediates - quinone methides (QMs). This study describes preparation of QM precursor, 2-hydroxy-3-hydroxymethylanthracene (2) and a detailed photochemical and photobiological investigation on similar anthracene derivatives 3 and 4. Upon photoexcitation with near visible light at λ > 400 nm 1 and 2 give QMs, that were detected by laser flash photolysis and their reactivity with nucleophiles has been demonstrated in the preparative irradiation experiments where the corresponding adducts were isolated and characterized. 3 and 4 cannot undergo photodehydration and deliver QM, but lead to the formation of phenoxyl radical and singlet oxygen, respectively. The activity of 1–4 was tested on a panel of human tumor cell lines, while special attention was devoted to demonstrate their potential selectivity towards the cells with CSC-like properties (HMLEshEcad). Upon the irradiation of cell lines treated with 1–4, an enhancement of antiproliferative activity was demonstrated, but the DNA was not the target molecule. Confocal microscopy revealed that these compounds entered the cell and, upon irradiation, reacted with cellular membranes. Our experiments demonstrated moderate selectivity of 2 and 4 towards CSC-like cells, while necrosis was shown to be a dominant cell death mechanism. Especially interesting was the selectivity of 4 that produced higher levels of ROS in CSC-like cells, which forms the basis for further research on cancer phototherapy, as well as for the elucidation of the underlying mechanism of the observed CSC selectivity based on oxidative stress activation.
- Uzelac, Lidija,?kalamera, ?ani,Mlinari?-Majerski, Kata,Basari?, Nikola,Kralj, Marijeta
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- Selective two-photon-absorption-induced reactions of anthracene-2-carboxylic acid on tunable plasmonic substrate with incoherent light source
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In this research, we report the development, characterization and application of various plasmonic substrates (with localized surface plasmon resonance wavelength tunable by gold nanoparticle size) for two-photon absorption (TPA)-induced photodimerization of an anthracene derivative, anthracene carboxylic acid, in both surface and solution phase under incoherent visible light irradiation. Despite the efficient photoreaction property of anthracene derivatives and the huge number of publications about them, there has never been a report of a multiphoton photoreaction involving an anthracene derivative with the exception of a reverse photoconversion of anthracene photodimer to monomer with three-photon absorption. We examined the progress of the TPA-induced photoreaction by means of surface-enhanced Raman scattering, taking advantage of the ability of our plasmonic substrate to enhance and localize both incident light for photoreaction and Raman scattering signal for analysis of photoreaction products. The TPA-induced photoreaction in the case of anthracene carboxylic acid coated 2D array of gold nanoparticles gave different results according to the properties of the plasmonic substrate, such as the size of the gold nanoparticle and also its resultant optical properties. In particular, a stringent requirement to achieve TPA-induced photodimerization was found to be the matching between irradiation wavelength, localized surface plasmon resonance of the 2D array, and twice the wavelength of the molecular excitation of the target material (in this case, anthracene carboxylic acid). These results will be useful for the future development of efficient plasmonic substrates for TPA-induced photoreactions with various materials.
- Pincella, Francesca,Isozaki, Katsuhiro,Taguchi, Tomoya,Song, Yeji,Miki, Kazushi
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- 2-Anthrylmethoxyacetic acid, a new chiral anisotropic reagent for elucidating the absolute configuration of acyclic alcohols
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(R) and (S)-2-anthrylmethoxyacetic acids (2ATMA) have been prepared to elucidate the absolute configuration of long-chain compounds containing a secondary hydroxy group, methyl 9-hydroxystearate and 10-nonacosanol (ginnol).
- Kouda, Kyoji,Kusumi, Takenori,Ping, Xu,Kan, Yukiko,Hashimoto, Toshihiro,Asakawa, Yoshinori
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- Electron Paramagnetic Resonance, ENDOR and TRIPLE Resonance Study of Some 9,10-Anthraquinone Radicals in Solution
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EPR, ENDOR and TRIPLE resonance spectra were recorded for 1,8-dihydroxy-3-methyl-9,10-anthraquinone and 9,10-anthraquinone-2-carboxylic acid anion radicals and the 9,10-anthraquinol-2-carboxylic acid cation radical.EPR spectra were recorded for the 5,8-dideuterio-1,4-dideuterioxy-9,10-anthraquinone anion radical, the 6,7-dideuterio-1,4-dideuterioxy-9,10-anthraquinone anion radical and the 1,4-dihydroxy-9,10-anthraquinol cation radical.The coupling constants of the 1,4-dihydroxy-9,10-anthraquinone anion radical were assigned by deuteriation. KEY WORDS: Substituted 9,10-anthraquinone radicals, EPR, ENDOR
- Vuolle, Mikko,Maekelae, Reijo
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- X-ray crystal structures of two solvent complexes involving positionally isomeric 9,10-anthraquinonecarboxylic acids and DMSO
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Two constitutionally isomeric 9,10-anthraquinonecarboxylic acids 1 and 2 are reported to yield DMSO-solvated crystals (1a and 2a) on the crystallization from DMSO. The molecular and crystal structures are described and comparatively discussed with reference to the effect implicated by the different position of the carboxylic group at the anthraquinone basis and the involvement of the solvent molecule.
- Gruber, Tobias,Helas, Stefanie F.,Seichter, Wilhelm,Weber, Edwin
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- Inhibitory activities of anthraquinone and xanthone derivatives against transthyretin amyloidogenesis
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Transthyretin is a tetrameric protein which functions as a transporter of thyroxine and retinol-binding protein. Misfolding and amyloid aggregation of transthyretin are known to cause wild-type and hereditary transthyretin amyloidosis. Stabilization of the transthyretin tetramer by low molecular weight compounds is an efficacious strategy to inhibit the aggregation pathway in the amyloidosis. Here, we investigated the inhibitory activities of anthraquinone and xanthone derivatives against amyloid aggregation, and found that xanthone-2-carboxylic acid with one chlorine or methyl group has strong inhibitory activity comparable with that of diflunisal, which is one of the best known stabilizers of transthyretin. X-ray crystallographic structures of transthyretin in complex with the compounds revealed that the introduction of chlorine, which is buried in a hydrophobic region, is important for the strong inhibitory effect of the stabilizer against amyloidogenesis. An in vitro absorption, distribution, metabolism and elimination (ADME) study and in vivo pharmacokinetic study demonstrated that the compounds have drug-like features, suggesting that they have potential as therapeutic agents to stabilize transthyretin.
- Kitakami, Ryota,Inui, Kishin,Nakagawa, Yusuke,Sawai, Yurika,Katayama, Wakana,Yokoyama, Takeshi,Okada, Takuya,Kanamitsu, Kayoko,Nakagawa, Shinsaku,Toyooka, Naoki,Mizuguchi, Mineyuki
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- Oxidative α-C-C Bond Cleavage of 2° and 3° Alcohols to Aromatic Acids with O2at Room Temperature via Iron Photocatalysis
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The selective α-C-C bond cleavage of unfunctionalized secondary (2°) and tertiary alcohols (3°) is essential for valorization of macromolecules and biopolymers. We developed a blue-light-driven iron catalysis for aerobic oxidation of 2° and 3° alcohols to acids via α-C-C bond cleavages at room temperature. The first example of oxygenation of the simple tertiary alcohols was reported. The iron catalyst and blue light play critical roles to enable the formation of highly reactive O radicals from alcohols and the consequent two α-C-C bond cleavages.
- Zhang, Zongnan,Zhang, Guoxiang,Xiong, Ni,Xue, Ting,Zhang, Junjie,Bai, Lu,Guo, Qinyue,Zeng, Rong
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supporting information
p. 2915 - 2920
(2021/05/05)
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- Design, synthesis, and molecular docking studies of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives as xanthine oxidase inhibitors
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A series of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives (1a–j) was designed and synthesized as novel xanthine oxidase inhibitors. Among them, the L/D-phenylalanine derivatives (1d and 1i) and the L/D-tryptophan derivatives (1e and 1j) were effective with micromolar level potency. In particular, the L-phenylalanine derivative 1d (IC50?=?3.0?μm) and the D-phenylalanine derivative 1i (IC50?=?2.9?μm) presented the highest potency and were both more potent than the positive control allopurinol (IC50?=?8.1?μm). Preliminary SAR analysis pointed that an aromatic amino acid fragment, for example, phenylalanine or tryptophan, was essential for the inhibition; the D-amino acid derivative presented equal or greater potency compared to its L-enantiomer; and the 9,10-anthraquinone moiety was welcome for the inhibition. Molecular simulations provided rational binding models for compounds 1d and 1i in the xanthine oxidase active pocket. As a result, compounds 1d and 1i could be promising lead compounds for further investigation.
- Zhang, Ting-Jian,Li, Song-Ye,Yuan, Wei-Yan,Zhang, Yi,Meng, Fan-Hao
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p. 893 - 901
(2018/03/21)
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- 2 - substituted - 9, 10 - anthraquinone compound, preparation method and use thereof
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The invention belongs to the technical field of medicine, and particularly relates to 2-substituted-9,10-anthraquinone compounds represented by the general formula I, the general formula II, the general formula III and the general formula IV, and pharmaceutically acceptable salts, hydrates or solvates and pharmaceutically acceptable carriers thereof. A preparation method comprises the steps: with phthalic anhydride as a starting material, carrying out a Friedel-Crafts reaction, concentrated sulfuric acid dehydration, NBS bromization and sodium azide substitution, generating a key intermediate 2-azide methyl-9,10-anthraquinone, and finally in the presence of copper sulfate pentahydrate and vitamin C, carrying out a Husigen cycloaddition reaction with substituted alkyne; or carrying out concentrated sulfuric acid dehydration, cyclization, chromium trioxide oxidation and thionyl chloride chlorination, to obtain anthraquinone-2-formyl chloride, then carrying out an acylation reaction with various L-amino acid methyl esters, further hydrolyzing, and thus obtaining the target compounds. The prepared compounds show good results in in-vitro antitumor activity tests.
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- The photocatalytic oxidation 2 - ethyl anthraquinone preparing anthraquinone - 2 - carboxylic acid
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The invention belongs to a method for preparing anthraquinone-2-carboxylic acid by virtue of photo-catalytic oxidation of 2-ethyl anthraquinone. The method comprises the following steps: dissolving 2-ethyl anthraquinone into a solvent, adding a photocatalyst and hydrogen peroxide, carrying out illumination catalytic oxidation reaction until 2-ethyl anthraquinone is optically catalyzed and oxidized; after the reaction is finished, filtering the catalyst, carrying out reduced pressure distillation on filtrate to remove the solvent, and carrying out cooling and crystallization, so as to prepare anthraquinone-2-carboxylic acid, wherein the photocatalyst is titanium dioxide or zinc oxide, and the solvent is acetonitrile or N,N-dimethylformamide. The method for synthesizing anthraquinone-2-carboxylic acid by virtue of photo-catalytic oxidation of 2-ethyl anthraquinone has the beneficial effects that the operation is convenient, the cost is relatively low, the discharge load of wastewater is low, and the industrialization is easily realized.
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Paragraph 0018-0024; 0025-0031; 0032-0038; 0039-0045
(2017/09/26)
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- Use of linker for preparation of missing solid-state photoproducts: Head-to-head photodimerization of anthracene-9-propionic acid in its crystalline double salt with cyclohexane-1,2-diamine
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In order to realize the uncommon head-to-head photodimerization of 9-substituted anthracenes rather than the common head-to-tail photodimerization, a regiochemical control of the reaction through use of supramolecular linkers has been attempted in the solid state. Thus, crystalline double salts are prepared from anthracene-9-propionic acid (9-AP) and 1,2-diamines such as ethylenediamine (en), racemic or optically active (R,R)- or (S,S)-trans-cyclohexane-1,2-diamine (t-chxn), and cis-cyclohexane-1,2-diamine (c-chxn), and these salts are irradiated in the solid state. The 1,2-diamine is used as a linker molecule to connect two molecules of 9-AP by formation of a double salt. Like the previously published head-to-head photodimerization of (E)-cinnamic acids, the head-to-head photodimer of 9-AP is successfully produced from solid-state photolysis of the double salts of gauche 1,2-diamines, i.e. (R,R)- and (S,S)-t-chxn and c-chxn. The crystal structure for the low-photoreactivity double salt with (±)-t-chxn has been successfully solved.
- Ito, Yoshikatsu,Olovsson, Gunnar
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p. 127 - 133
(2007/10/03)
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- Synthesis and Properties of Anthraquinone-Substituted Porphyrin Compounds
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A synthetic route for the preparation of covalently-linked porphyrin-anthraquinone compounds as models for the phototrap in photosynthesis is described. 5-(2-anthraquinone)-15-(N,N-dimethylaminobenzal)-2,8,12,18-tetraethyl-3,7,13,17-tetramethylporphyrin (DPQ) and its derivatives are synthesized by condensation of 3,3'-diethyl-4,4'-dimethyl-2,2'-dipyrrolylmethane with an appropriate aldehyde in good molecular orientation and higher yield.The structures of new compounds are determined by 1H NMR, UV-visible spectroscopy, FTIR spectroscopy, mass spectrometry and elemental analytical data.Some of the photophysical properties of the compounds are reported with reference to their use as models of the reaction centre in photosynthesis.
- Zhang, Jie,Yang, Guo-Yu,Wen, Ke,Sun, Hao-Ran,Yu, Lian-Xiang,Cao, Xi-Zhang
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p. 613 - 618
(2007/10/03)
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- Process for preparation of 2-substituted 1,4-naphthoquinone
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A process for preparation of a 2-substituted-1,4-naphthoquinone which comprises oxidizing a 2-substituted naphthalene to obtain reaction products comprising a 2-substituted-1,4-naphthoquinone and a 6-substituted-1,4-naphthoquinone; adding a diene compound to the reaction products and heating the mixture to form a Diels-Alder reaction adduct between the diene compound and the 6-substituted-1,4-naphthoquinone in the reaction products; and separating the 2-substituted-1,4-naphthoquinone from the adduct.
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- α-Chlorination process
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A process for α-chlorination of side chains of electronegatively substituted aromatic compounds with dichlorine monoxide.
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- Cyclic carbonyl compounds
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Certain fluorenone and anthraquinone compounds, each of which is 2-substituted by a carboxyl group or a salt, ester or optionally substituted amide thereof and each of which is optionally substituted in the 5,6-,7-or 8-position, by a second carboxyl group, salt, ester or optionally substituted amide thereof, the substitutent in the 5,6-7- or 8-position of the fluorenone compounds, also being selected from cyano, halogen, nitro, alkyl, alkoxy and acyl, are useful for the relief or prophylaxis of allergic conditions.
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- Cyclic carbonyl compounds
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Certain fluorenone and anthraquinone compounds, each of which is 2-substituted by a carboxyl group or a salt, ester or optionally substituted amide thereof and each of which is optionally substituted in the 5,6-,7- or 8- position, by a second carboxyl group, salt, ester or optionally substituted amide thereof, the substitutent in the 5,6-7- or 8- position of the fluorenone compounds, also being selected from cyano, halogen, nitro, alkyl, alkoxy and acyl, are useful for the relief or prophylaxis of allergic conditions.
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