Potent antitumor activity of synthetic 1,2-Naphthoquinones and 1,4-Naphthoquinones

Kongkathip, Ngampong; Kongkathip, Boonsong; Siripong, Pongpun; Sangma, Chak; Luangkamin, Suwaporn; Niyomdecha, Momad; Pattanapa, Suppachai; Piyaviriyagul, Suratsawadee; Kongsaeree, Palangpon

doi:10.1016/s0968-0896(03)00226-8

Cited by 206 publications

(145 citation statements)

References 26 publications

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“…All conjugates induced DNA fragmentation, a process that may involve ROS generation as suggested by data obtained with 5c. Our results corroborate work of other groups where modification of 1,4-naphthoquinones also induced increase in antitumoral activity reinforcing the importance of this approach for the development of more active drugs (28)(29)(30). Figure 6.…”

Section: Discussionsupporting

confidence: 90%

Antitumoral activity of new polyamine-naphthoquinone conjugates

Esteves-Souza

Lúcio²,

Cunha³

et al. 2008

Oncol Rep

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Abstract. Polyamine-naphthoquinone conjugates 5a-c were synthesized by nucleophilic displacement of 2-methoxylawsone 3a, 2-methoxylapachol 3b and 2-methoxy-norlapachol 3c with the polyamine N1-Boc-N5-Bn-spermidine 4. Unprotected derivatives 6a-c were synthesized to evaluate the effect of the protective Boc group on the activity of compounds 5a-c. The colorimetric MTT assay was used to evaluate their cytotoxic activity. All compounds were active against human lines of promyelocytic leukemia (HL-60), lung cancer (GLC4), Burkitt lymphoma (Daudi) and a mouse breast tumor (Ehrlich carcinoma), but only unprotected 6a-c showed activity against the human line of melanoma (MV-3). IC 50 values were obtained from dose response curves by linear regression. DNA fragmentation was measured by quantification of the subG1 peak of the cell cycle. Apoptosis of HL-60 treated with 5c was dose-dependent. The amount of DNA fragmentation observed by exposure of HL-60 to 25 μM of compounds 5a-c and 6a-c is compatible with the decrease in viability induced by the drugs at this concentration. Production of ROS was measured by H2-CFDA. Kinetics of HL-60 DNA fragmentation and ROS formation by 5c indicated that production of ROS precedes cell death. In conclusion, spermidine-1,4-naphthoquinone conjugates exhibited an increase in activity compared with the natural products and induced apoptosis of tumor cell lines by a mechanism that is mediated, at least in part, by ROS production.

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Section: Discussionsupporting

confidence: 90%

Antitumoral activity of new polyamine-naphthoquinone conjugates

Esteves-Souza

Lúcio²,

Cunha³

et al. 2008

Oncol Rep

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“…Reduction of corresponding cyclic ester 24 led to diol 26 which was oxidized by treating with Fremy's salt 11) to give naphthoquinone 28. Oxidation of quinone 28 with 2, in the presence of para-toluene sulfonic acid (p-TsOH) provided rhinacanthone derivative 30 which was treated with 1% aqueous sodium hydroxide to afford naphthoquinone alcohol 32. The yields in all steps involved were very high.…”

Section: Resultsmentioning

confidence: 99%

“…Key words: naphthoquinone ester; rhinacanthin derivative; cytotoxicity; cancer cell lines Rhinacanthins 1) (1,4-naphthoquinone esters) and rhinacanthone 2) were isolated from the Thai herb, Rhinacanthus nasutus, [3][4][5] which is used for treating cancer. 6) An aqueous extract of the roots of R. nasutus has recently been examined in mice for its chemopreventive potential against colonic neoplasms induced by azoxymethane combined with dextran sodium sulfate.…”

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Synthesis and Anticancer Evaluation of Naphthoquinone Esters with 2′-Cyclopentyl and 2′-Cyclohexyl Substituents

Kongkathip

Pradidphol

Hasitapan

et al. 2010

Bioscience, Biotechnology, and Biochemistry

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“…The leaf petroleum ether fraction shows significant mosquitocidal activity [7]. It has been reported that rhinacanthin-C, rhinacanthin-D and rhinacanthin-N isolated from R. nasutus possessed various biological activities [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

In Vitro Phytochemical and Antibacterial Studies on Rhinacanthus Nasutus (L.) Kurz - A Medicinally Important Plant

Antonysamy¹

2017

JMEN

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The present study was aimed to evaluate and compare the phytochemical and antibacterial potential of mother plants (aerial parts), in vitro leaves and stems derived callus and in vitro callus mediated shootlets of Rhinacanthus nasutus (L.) Kurz. Preliminary phytochemical analysis and extraction was performed on stem and leaves segments derived calli (4 weeks old), aerial portions of mother plants and calli mediated shootlets of R. naustus. Anti-bacterial activity of different extracts (25 µg) (ethanol, chloroform, aqueous and ethyl acetate) of stem and leaves segments derived calli, aerial portions of mother plants and calli mediated shootlets were investigated by well-diffusion method against Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumoniae, Bacillus subtilis and Escherichia coli. The preliminary phytochemical studies confirmed that the leaves and stem derived calli mediated shootlets showed the higher degree of metabolite constituents and extraction value compared to the in vitro derived calli and in vivo leaves and stem (aerial portions). The ethyl acetate extracted solvents showed the maximum bio-efficacy compared with other solvents due to the presence of more compounds such as saponins, steroids, tannins, phenolics, triterpenoids, alkaloids, coumarins, anthraquinones, glycosides and flavonoids. The present study observation suggested that a possibility to establish high yielding genotypes by in vitro culture for production of medicinally important bioactive compounds. The methods developed in this work make possible for the low volume and high potential production of active principles under in vitro condition in short duration with less amount of explants utilization. .

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Potent antitumor activity of synthetic 1,2-Naphthoquinones and 1,4-Naphthoquinones

Cited by 206 publications

References 26 publications

Antitumoral activity of new polyamine-naphthoquinone conjugates

Antitumoral activity of new polyamine-naphthoquinone conjugates

Synthesis and Anticancer Evaluation of Naphthoquinone Esters with 2′-Cyclopentyl and 2′-Cyclohexyl Substituents

In Vitro Phytochemical and Antibacterial Studies on Rhinacanthus Nasutus (L.) Kurz - A Medicinally Important Plant

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