117-78-2Relevant articles and documents
Synthesis of water-soluble 9,10-anthraquinone analogues with potent cyanobactericidal activity toward the musty-odor cyanobacterium Oscillatoria perornata
Nanayakkara, N. P. Dhammika,Schrader, Kevin K.
, p. 1002 - 1007 (2008)
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.
The design and synthesis of a photo-controlled, peptide-based potential drug carrier
Parlak Khalily, Melek,?z?ubuk?u, Salih
, p. 1136 - 1145 (2018)
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.
High-sensitivity HPLC quantification of nonfluorescent but photolabile analyte through photoreversion in fluorescence detector
Nishijima, Masaki,Wada, Takehiko,Nagamori, Koushi,Inoue, Yoshihisa
, p. 726 - 727 (2009)
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
Selective photocytotoxicity of anthrols on cancer stem-like cells: The effect of quinone methides or reactive oxygen species
Uzelac, Lidija,?kalamera, ?ani,Mlinari?-Majerski, Kata,Basari?, Nikola,Kralj, Marijeta
, p. 558 - 574 (2017)
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.
Sonoda et al.
, p. 853,856 (1962)
Electron Paramagnetic Resonance, ENDOR and TRIPLE Resonance Study of Some 9,10-Anthraquinone Radicals in Solution
Vuolle, Mikko,Maekelae, Reijo
, p. 987 - 991 (1992)
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
Inhibitory activities of anthraquinone and xanthone derivatives against transthyretin amyloidogenesis
Kitakami, Ryota,Inui, Kishin,Nakagawa, Yusuke,Sawai, Yurika,Katayama, Wakana,Yokoyama, Takeshi,Okada, Takuya,Kanamitsu, Kayoko,Nakagawa, Shinsaku,Toyooka, Naoki,Mizuguchi, Mineyuki
, (2021/07/06)
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.
Design, synthesis, and molecular docking studies of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives as xanthine oxidase inhibitors
Zhang, Ting-Jian,Li, Song-Ye,Yuan, Wei-Yan,Zhang, Yi,Meng, Fan-Hao
, p. 893 - 901 (2018/03/21)
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.
