Synthesis and Cytotoxic Activity of Benzo[a]pyrano[3,2-h] and [2,3-i]xanthone Analogues of Psorospermine, Acronycine, and Benzo[a]acronycine

Sittisombut, Chavalit; Boutefnouchet, Sabrina; Van-Dufat, Hanh Trinh; Tian, Wen; Michel, Sylvie; Koch, Michel; Tillequin, François; Pfeiffer, Bruno

doi:10.1248/cpb.54.1113

Cited by 17 publications

(9 citation statements)

References 26 publications

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“…Especially, the effective inhibitory activity against human cancer cell lines has attracted considerable attention. [6][7][8][9][10] The preliminary work has highlighted the high potentials of xanthones as a promising building motif for the development of a new class of potent anticancer drugs.…”

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confidence: 99%

Antitumor Activity and DNA-Binding Investigations of Isoeuxanthone and Its Piperidinyl Derivative

Wang

Wei

Yan

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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The binding mode and affinity of isoeuxanthone (1,6-dihydroxyxanthone) (1) and its piperidinyl derivative (1-hydroxy-6-(2-(1-piperidinyl)ethoxy)xanthone) (2) with calf thymus DNA were studied using absorption spectroscopy, fluorescence spectroscopy, circular dichroism (CD) spectroscopy and viscosity measurements. Results indicate that the two xanthones can intercalate into the DNA base pairs by the plane of xanthone ring and the binding affinity of the piperidinylethoxy substituted xanthone 2 is stronger than 1. In addition, the cytotoxic effects of both compounds were evaluated with the human cervical cancer cell line (HeLa) and human hepatocellular liver carcinoma cell line (HepG2) using acid phosphatase assay. Analyses show that the piperidinylethoxy substituted xanthone exhibits more effective cytotoxic activity than isoeuxanthone against the two cancer cells. The effects on the inhibition of tumor cells in vitro agree with the studies of DNAbinding.

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confidence: 99%

Antitumor Activity and DNA-Binding Investigations of Isoeuxanthone and Its Piperidinyl Derivative

Wang

Wei

Yan

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Materials The benzoxanthones 1 and 2 were prepared according to the literatures [13][14][15] with some improvement. Calf thymus DNA (ct DNA) and ethidium bromide (EB) were obtained from Sigma Chemical Co. All the measurements were carried out in doubly distilled water buffer containing 5 mM Tris and 50 mM NaCl, and adjusted to pH 7.4 with hydrochloric acid.…”

Section: Methodsmentioning

confidence: 99%

Cytotoxic Activity and DNA-Binding Investigations of Two Benzoxanthone Derivatives

Wang

Shen

Jia

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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Natural products play a major role in anticancer drug discovery as a unique source of original structures which can provide models for future drug design. Xanthone compounds, secondary metabolites from higher plants and microorganisms, have very diverse biological profiles including anti-hypertensive, anti-oxidative, anti-thrombotic, and anticancer activity, based on their diverse structures.1-7) During the past several years, the xanthone template has generated a growing interest in the search for new antitumor agents. 8)The preliminary work has highlighted the high potentials of xanthones as a promising building motif for the development of a new class of potent anticancer drugs.Numerous biological experiments have demonstrated that DNA is one of the primary intracellular targets of anti-cancer drugs due to the interaction of small molecules with DNA, which cause DNA damage in cancer cells, block the division of cancer cells and result in cell death. 9) Up to now, few systematic studies of the interaction of xanthones and their derivatives with DNA have been reported. [10][11][12] However, their structure-activity relationships remain unestablished in the xanthones system. Benzoxanthones having four extended and conjugated fused rings may be viewed as flavone derivatives in which the phenyl group is fused with two aromatic rings. The structural features inherent in benzoxanthones, makes us aware that the conjugated p-systems in benzoxanthones may contribute significantly to the biological activity. The primary aim of this work was to gain some insight into the effect of structural factor in benzoxanthones on the probable binding mode and binding affinity toward DNA.In this work, the binding mode on the interactions of two benzoxanthones 1,3-dihydroxy-12H-benzo[b]xanthen-12-one (1) and 9,11-dihydroxy-12H-benzo[a]xanthen-12-one (2) (shown in Fig. 1) with DNA was investigated by different kinds of spectrophotometric methods and viscosity measurements. The studies suggest that intercalative binding mode appears to be acceptable. In addition, the benzoxanthones were evaluated for cytotoxic activities toward human cervical cancer cell line (HeLa), human hepatocellular liver carcinoma cell (HepG2) and human normal liver cell line (L02) by acid phosphatase assay. ExperimentalMaterials The benzoxanthones 1 and 2 were prepared according to the literatures [13][14][15] with some improvement. Calf thymus DNA (ct DNA) and ethidium bromide (EB) were obtained from Sigma Chemical Co. All the measurements were carried out in doubly distilled water buffer containing 5 mM Tris and 50 mM NaCl, and adjusted to pH 7.4 with hydrochloric acid. The concentration of DNA solution was determined from UV absorption at 260 nm using a molar absorption coefficient e 260 ϭ6600 mol Ϫ1 cm Ϫ1. Purity of the DNA was checked by monitoring the ratio of the absorbance at 260 nm to that at 280 nm. The solution gave a ratio of A 260 /A 280 Ͼ1.80, indicating that DNA was sufficiently free from protein. 16,17)Physical Measurements The UV-Vis absorption ...

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“…Especially, the effective inhibitory activity against human cancer cell lines has attracted considerable attention and many xanthone derivatives with excellent anticancer activity have been obtained. [12][13][14][15] For example, Shen et al reported xanthone derivatives substituted by six different groups, of which the piperidinylethoxy-substituted xanthone could efficiently prohibit the growth of cancer cells. 16 Although preliminary work has highlighted the high class of the potent anticancer potentials of xanthone as a promising building motif for the development of new drugs, more efforts on structural modification of xanthone as well as on their pharmacological activity should be realized.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel benzo[b]xanthone derivatives as potential antitumor agents

Luo

Qin

Dai

et al. 2013

JSCS

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Nine novel aminoalkoxy substituted benzoxanthones (3a-3i) were synthesized. Their antitumor activities were evaluated in five human solid tumor cell lines including Hep-G2, BEL-7402, HeLa, MGC-803 and CNE by MTT method. The results showed that most of the compounds displayed moderate to good inhibitory activities on the tested cancer cell lines in vitro, among them compounds 3a and 3h showed higher antitumor activity than other tested compounds against most cell lines. The influence of two kinds of structural factors including the terminal amino group and length of carbon spacers on the anticancer activities were explored to discuss the preliminary structure-activity relationships

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Synthesis and Cytotoxic Activity of Benzo[a]pyrano[3,2-h] and [2,3-i]xanthone Analogues of Psorospermine, Acronycine, and Benzo[a]acronycine

Cited by 17 publications

References 26 publications

Antitumor Activity and DNA-Binding Investigations of Isoeuxanthone and Its Piperidinyl Derivative

Antitumor Activity and DNA-Binding Investigations of Isoeuxanthone and Its Piperidinyl Derivative

Cytotoxic Activity and DNA-Binding Investigations of Two Benzoxanthone Derivatives

Synthesis and biological evaluation of novel benzo[b]xanthone derivatives as potential antitumor agents

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