Synthesis and biological evaluation of new derivatives of emodin

Teich, Lars; Daub, Katja S.; Krügel, Vera; Nissler, Ludwig; Gebhardt, Rolf; Eger, Kurt

doi:10.1016/j.bmc.2004.08.024

Cited by 38 publications

(41 citation statements)

References 15 publications

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“…It is well known that anthraquinones can bind DNA by inserting and stacking between the base pairs of DNA double helices (Silverman, 2004). There are several proposed mechanisms regarding the drug's anticancer activity: one involves the drug's capability to intercalate DNA (Piedade et al, 2002;Hsiao et al, 2008) and to inhibit DNA topoisomerase II (Capranico et al, 1994;Perchellet et al, 2000;Teich et al, 2004;Dal Ben et al, 2007) and the other involves the drug's ability to produce free radicals and consequently to cleave DNA (Fisher et al, 1992;Tütem et al, 1996). In a recent study, we showed that derivatives of 2-(1-hydroxyalkyl)-1,4-dihydroxyl-9,10-anthraquinone displayed antitumor activity (Jin et al, 1998a(Jin et al, , 1998bTam et al, 2000).…”

Section: Introductionmentioning

confidence: 98%

Synthesis and antiproliferative activity of 1,4-bis(dimethylamino)-9,10-anthraquinone derivatives against P388 mouse leukemic tumor cells

Jin

2011

Arch. Pharm. Res.

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A series of 2-substituted-1,4-bis(dimethylamino)-9,10-anthraquinone derivatives were synthesized and their in vitro antiproliferative activities against p388 mouse leukemic tumor cells were evaluated. In addition, the effect of substituents on the phenyl ring was investigated. Among the derivatives tested, seven showed a high antiproliferative effect and three showed a moderate effect. In addition, introduction of a series of substituted phenyl groups into 1,4-bis(dimethylamino)-9,10-anthraquinone at 2-position were shown to enhance its antiproliferative activity. The antiproliferative activity also increased upon substitution of the benzene ring by an electron donating group such as an amine or methoxyl group.

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Section: Introductionmentioning

confidence: 98%

Synthesis and antiproliferative activity of 1,4-bis(dimethylamino)-9,10-anthraquinone derivatives against P388 mouse leukemic tumor cells

Jin

2011

Arch. Pharm. Res.

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“…[1] Drugs of the anthraquinone (AQ) family include potent cytotoxic compounds, such as doxorubicin and mitoxantrone, mainly acting by DNA intercalation and subsequent inhibition of DNA topoisomerase II; emodin was also shown to exert a growth-inhibitory effect on cancer cell in vitro, [2] and on in vivo tumor models, [3] possibly due to its ability to interfere with the catalytic activity of casein kinase II (CK2). [4] Furthermore, emodin, or its derivatives, can be considered as the precursor in the synthesis of hypericin, [1] a naturally occurring compound found in the common St. Johns wort (Hypericum species), which has been recently used as a promising novel therapeutic and diagnostic agent in the detection and treatment of tumors, particularly in the case of bladder cancer.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Porphyrin‐Anthraquinone Conjugates as Photosensitizing Agents

Banfi

Caruso

Gariboldi

et al. 2008

Synthetic Communications

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A series of 5,10,15,20-tetraarylporphyrins covalently linked to anthraquinones belonging to the class of emodin were synthesized following two different pathways. The first method exploits the functionalization of the methyl group in position 6 of O-protected emodins, which can be converted either into a carboxylic acid or into a bromo-methyl derivative. The modified emodins were then bound through amido or ether bonds to one of the tetraarylporphyrins meso phenyl rings bearing an amino or hydroxyl group, respectively. An alternative synthesis exploits the mixed condensation of triacetoxy-emodinaldehyde (or trimethoxy-emodinaldehyde) with pyrrole in the presence of variable amounts of benzaldehyde, thus affording two similar 5-emodin-10,15,20-triphenylporphyrins differing from one another in the emodin hydroxyl group protection. These compounds are characterized by direct conjugation of the emodin moiety to the tetrapyrrolic ring. Preliminary experiments were performed in vitro on the human colon adenocarcinoma cell line HCT116 to evaluate the photocytotoxicity of the new compounds.

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“…[2] At present, most well-developed drug molecules bearing five-membered-ring heterocycles contain at least one planar aromatic ring, whereas three-dimensional compounds are used less often, for two possible reasons:F irst, heteroaromatic compounds can be obtained from aw ealth of sources,and there have been outstanding achievements made in the coupling of such segments.S econd, methods for constructing three-dimensional compounds are still limited, especially for highly enantiomerically enriched compounds. [5][6][7][8] During our research on the development of transitionmetal-catalyzed allylic dearomatization reactions, [9] which are ap owerful class of catalytic asymmetric dearomatization (CADA) reactions, [10] we recently realized iridium-catalyzed allylic dearomatization reactions of electron-deficient Nheteroaromatic compounds. [3] We envisioned that the dearomatization of nitrogen-containing aromatic compounds in one step to provide three-dimensional compounds would be ap romising approach for accessing chiral heterocycles.…”

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confidence: 99%