Synthesis and anti-HIV-1 activities of novel podophyllotoxin derivatives

Chen, Shi‐Wu; Wang, Yunhua; Jin, Yan; Tian, Xuan; Zheng, Yong‐Tang; Luo, Du‐Qiang; Tu, Yong‐Qiang

doi:10.1016/j.bmcl.2006.11.070

Cited by 57 publications

(30 citation statements)

References 23 publications

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“…The reaction of hydrazoic acid with podophyllotoxin in the presence of BF 3 -Et 2 O gave 4-β-azido derivative 2 [6]. Nextly, the compound 4β-amino-4-deoxypodophyllotoxin 3 was prepared by reduction of the azide using Pd/C as a catalyst according to the procedure reported previously [14].…”

Section: Synthesis Of Aroylthiourea Derivatives Of Podophyllotoxinmentioning

confidence: 99%

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Synthesis and antitumor activity of novel aroylthiourea derivatives of podophyllotoxin

Zhao

Wang

et al. 2010

Invest New Drugs

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A novel series of 4β-[(4-substituted) aroylthiourea] derivatives of podophyllotoxin were synthesized and their abilities to inhibit the growth of cancer cells were investigated by MTT assay. Compound 4a possessed the highest cytotoxicity on HepG2, A549 and HCT-116 cancer cell lines with the IC(50) values of 0.1 μM. Apoptosis in HCT-116 cells induced by compound 4a was observed by Hoechst33342-Propidium iodide (PI) and acridine orange (AO)-ethidium bromide (EB) double staining assays. DNA flow cytometric analysis revealed that 4a induced cell cycle arrest at G2/M phase and kDNA decatenation assay indicated that 4a inhibited topoisomerase IIα-mediated kDNA decatenation. Our results indicated that compound 4a possessed promising antitumor activity, which need to be studied further.

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Section: Synthesis Of Aroylthiourea Derivatives Of Podophyllotoxinmentioning

confidence: 99%

“…In order to obtain better therapeutic agents, a lot of derivatives of podophyllotoxin have been synthesized. New synthetic N-linked congeners like GL-331 and NPF exhibite improved cytotoxicity and topo-II inhibition activity [5][6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antitumor activity of novel aroylthiourea derivatives of podophyllotoxin

Zhao

Wang

et al. 2010

Invest New Drugs

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“…Etoposide, NaBH 4 , NaIO 4 , GSH, Nethylmaleimide (NEM), o-phthalaldehyde (OPA) and glutathione ethyl ester (GEE) were purchased from Sigma-Aldrich (St. Louis, MO). A stock solution of OPA was prepared by dissolving 50 mg of reagent grade OPA in 0.5 ml of methanol and diluting this to 5 mg/mL with 0.1 M sodium borate buffer at pH 9.90.…”

Section: Methodsmentioning

confidence: 99%

“…etoposide, teniposide and eto-pophos, are anticancer drugs widely used against several types of neoplasms including testicular and small-cell lung cancers, lymphoma, leukaemia, Ka-posi's sarcoma and others [1,2]. Other podophyllotoxin derivatives have been synthesized such as those reported recently [3,4]. The activity of cyclolignans against several types of cancers has also been described [2,5,6].…”

Section: Introductionmentioning

confidence: 99%

Thiols oxidation and covalent binding of BSA by cyclolignanic quinones are enhanced by the magnesium cation

Alegrı́a

Sanchez-Cruz

Kumar

et al. 2008

Free Radical Research

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A novel cyclolignanic quinone, 7-acetyl-3′,4′-didemethoxy-3′,4′-dioxopodophyllotoxin (CLQ), inhibits topoisomerase II (TOPO II) activity. The extent of this inhibition was greater than that produced by the etoposide quinone (EQ) or etoposide. Glutathione (GSH) reduces EQ and CLQ to their corresponding semiquinones under anaerobic conditions. The latter were detected by EPR spectroscopy in the presence of MgCl 2 but not in its absence. Semiquinone EPR spectra change with quinone/GSH mol ratio, suggesting covalent binding of GSH to the quinones. Quinone-GSH covalent adducts were isolated and identified by ESI-MS. These orthoquinones also react with nucleophilic groups from BSA to bind covalently under anaerobic conditions. BSA thiol consumption and covalent binding by these quinones are enhanced by MgCl 2 . Complex formation between the parent quinones and Mg +2 was also observed. Density functional calculations predict the observed blueshifts in the absorption spectra peaks and large decreases in the partial negative charge of electrophilic carbons at the quinone ring when the quinones are complexed to Mg +2 . These observations suggest a possible role of Mg +2 chelation by these quinones in increasing TOPO II thiol and/or amino/imino reactivity with these orthoquinones.

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“…Podophyllotoxin is a natural plant secondary metabolite which mainly exists in the root of P. hexandrum as well as its congeners and it is known to have importance in pharmacology and therapeutics as it contains anticancer, antineoplastic as well as anti HIV activities [3,29,30]. P. hexandrum obtained from India is better than its American counterpart, P. peltatum.…”

Section: Pharmacological Propertiesmentioning

confidence: 99%

Ethnopharmacology, phytochemistry and cytotoxicity of emerging biotechnological tool: Mayapple (Podophyllum hexandrum L.: Berberidaceae)

Butt¹,

Amjad²

2015

J Coast Life Med

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Synthesis and anti-HIV-1 activities of novel podophyllotoxin derivatives

Cited by 57 publications

References 23 publications

Synthesis and antitumor activity of novel aroylthiourea derivatives of podophyllotoxin

Synthesis and antitumor activity of novel aroylthiourea derivatives of podophyllotoxin

Thiols oxidation and covalent binding of BSA by cyclolignanic quinones are enhanced by the magnesium cation

Ethnopharmacology, phytochemistry and cytotoxicity of emerging biotechnological tool: Mayapple (Podophyllum hexandrum L.: Berberidaceae)

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