Anthracene-9, 10-dione derivatives induced apoptosis in human cervical cancer cell line (CaSki) by interfering with HPV E6 expression.

Abstract:

:A new series of anthracene-9, 10-dione derivatives have been synthesized to increase cytotoxic activity against human papillomavirus (HPV) positive cancer cell line, CaSki. The highest cytotoxicity was achieved by 4-(benzylamino)-9,10-dioxo-4a,9,9a,10-tetrahydroanthracen-1-yl 4-ethylbenzenesulfonate (5) with the inhibitory concentration 50 (IC50) of 0.3 μM which is 20 times lower than that of cisplatin (CDDP; IC50 = 8.0 μM). The toxicity against non-cancerous cell line, WI-38, was low with the IC50 > 10 μM. Treatment with this compound resulted in decreasing HPV E6 expression. Furthermore, increasing p53 and decreasing Bcl-2 expression were noted. Cell cycle profiles revealed an accumulation of cells in the G2/M phase.

journal_name

Eur J Med Chem

authors

Sangthong S,Sangphech N,Palaga T,Ngamrojanavanich N,Puthong S,Vilaivan T,Muangsin N

doi

10.1016/j.ejmech.2014.02.006

subject

Has Abstract

pub_date

2014-04-22 00:00:00

pages

334-42

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(14)00126-3

journal_volume

77

pub_type

杂志文章
  • Inclusion of a 5-fluorouracil moiety in nitrogenous bases derivatives as human carbonic anhydrase IX and XII inhibitors produced a targeted action against MDA-MB-231 and T47D breast cancer cells.

    abstract::A new series of pyrimidine derivatives as human carbonic anhydrases (CA, EC 4.2.1.1) inhibitors is here designed by including a 5-fluorouracil (5-FU) moiety, broadly used anticancer medication, in nitrogenous base modulators of the tumor-associated CAs. Most sulfonamide derivatives efficiently inhibit the target CA IX...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112112

    authors: Petreni A,Bonardi A,Lomelino C,Osman SM,ALOthman ZA,Eldehna WM,El-Haggar R,McKenna R,Nocentini A,Supuran CT

    更新日期:2020-03-15 00:00:00

  • Novel substituted quinoxaline 1,4-dioxides with in vitro antimycobacterial and anticandida activity.

    abstract::Thirty-six 6(7)-substituted-3-methyl- or 3-halogenomethyl-2-phenylthio-phenylsulphonyl-chloro-quinoxaline 1,4-dioxides belonging to series 3-6 were synthesised and submitted to a preliminary in vitro evaluation for antimycobacterial, anticandida and antibacterial activities. Antitubercular screening showed a generally...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(02)01346-6

    authors: Carta A,Paglietti G,Rahbar Nikookar ME,Sanna P,Sechi L,Zanetti S

    更新日期:2002-05-01 00:00:00

  • Potent naphthoquinones against antimony-sensitive and -resistant Leishmania parasites: synthesis of novel α- and nor-α-lapachone-based 1,2,3-triazoles by copper-catalyzed azide-alkyne cycloaddition.

    abstract::Continuing our screening program for novel anti-parasite compounds, we synthesized seven 1,4-naphthoquinones coupled to 1,2,3-triazoles, five nor-β-lapachone-based 1,2,3-triazoles and ten α-lapachone-based 1,2,3-triazoles. These and other naphthoquinonoid compounds were evaluated for their activity against promastigot...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.02.038

    authors: Guimarães TT,Pinto Mdo C,Lanza JS,Melo MN,do Monte-Neto RL,de Melo IM,Diogo EB,Ferreira VF,Camara CA,Valença WO,de Oliveira RN,Frézard F,da Silva EN Jr

    更新日期:2013-05-01 00:00:00

  • Rigid aromatic linking moiety in cationic lipids for enhanced gene transfection efficiency.

    abstract::Although numerous cationic lipids have been developed as non-viral gene vectors, the structure-activity relationship (SAR) of these materials remains unclear and needs further investigation. In this work, a series of lysine-derived cationic lipids containing linkages with different rigidity were designed and synthesiz...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.05.038

    authors: Wang B,Zhao RM,Zhang J,Liu YH,Huang Z,Yu QY,Yu XQ

    更新日期:2017-08-18 00:00:00

  • Design, synthesis and biological evaluation of small-azo-dyes as potent Vesicular Glutamate Transporters inhibitors.

    abstract::Vesicular Glutamate Transporters (VGLUTs) allow the loading of presynapic glutamate vesicles and thus play a critical role in glutamatergic synaptic transmission. VGLUTs have proved to be involved in several major neuropathologies and directly correlated to clinical dementia in Alzheimer and Parkinson's disease. Accor...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.03.056

    authors: Favre-Besse FC,Poirel O,Bersot T,Kim-Grellier E,Daumas S,El Mestikawy S,Acher FC,Pietrancosta N

    更新日期:2014-05-06 00:00:00

  • Synthesis, evaluation and 3D QSAR analysis of novel estradiol-RGD octapeptide conjugates with oral anti-osteoporosis activity.

    abstract::To enhance the potency, reduce the side effects and improve oral property of estradiol in estrogen replacement therapy (ERT), 6 novel estradiol-RGD octapeptide conjugates have been prepared. In an ovariectomized mouse osteoporotic model, at an oral dosage of 110.3 nmol/kg per day, their anti-osteoporosis activity was ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.09.036

    authors: Liu J,Zhang X,Zhao M,Peng S

    更新日期:2009-04-01 00:00:00

  • Design, synthesis and biological evaluation of piperazinyl-β-carbolinederivatives as anti-leishmanial agents.

    abstract::Molecular hybridization is a ligand based drug design approach is well known recent medicinal chemistry to design anti-parasitic agents. In the present study, we have designed a series of (1-phenyl-9H-pyrido [3,4-b]indol-3-yl) (4-phenylpiperazin-1-yl)methanone derivatives using molecular hybridization approach. Design...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.03.022

    authors: Ashok P,Chander S,Smith TK,Sankaranarayanan M

    更新日期:2018-04-25 00:00:00

  • Homology modeling and molecular dynamics of CYP1A1 and CYP2B1 to explore the metabolism of aryl derivatives by docking and experimental assays.

    abstract::Since many drugs are metabolized by cytochrome P450 (CYP450), biotransformation studies using these enzymes are valuable in drug development. In this work, the biotransformation by CYP1A1 and CYP2B1 of two acetylcholinesterase (AChE) inhibitors, 4-(4'-hydroxy-phenylamino)-4-oxo propanoic acid (A) and 1H-pyrrolidine-1-...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.07.055

    authors: Rosales-Hernández MC,Mendieta-Wejebe JE,Trujillo-Ferrara JG,Correa-Basurto J

    更新日期:2010-11-01 00:00:00

  • Synthesis and biological evaluation of novel structural hybrids of benzofuroxan derivatives and fluoroquinolones.

    abstract::A series of novel hybrids based on benzofuroxan derivatives and fluoroquinolones (4a-d-6a-d) have been synthesized. Unexpectedly, the reactions have resulted in salt products formation during the hydrolysis of benzofuroxans by water molecules being present in the solvent instead of usual substitution products. All the...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.03.086

    authors: Chugunova E,Akylbekov N,Bulatova A,Gavrilov N,Voloshina A,Kulik N,Zobov V,Dobrynin A,Syakaev V,Burilov A

    更新日期:2016-06-30 00:00:00

  • High anticancer potency on tumor cells of dehydroabietylamine Schiff-base derivatives and a copper(II) complex.

    abstract::Five bioactive dehydroabietylamine Schiff-base derivatives (L1-L5) had been synthesized from Dehydroabietylamine (L0), and the complex Cu(L1)2 had been obtained from the compound L1 and copper(II) acetate. Their activities against Hela (cervix), MCF-7 (breast), A549 (lung), HepG2 (liver) and HUVEC (umbilical vein, nor...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.01.041

    authors: Zhao F,Wang W,Lu W,Xu L,Yang S,Cai XM,Zhou M,Lei M,Ma M,Xu HJ,Cao F

    更新日期:2018-02-25 00:00:00

  • Design and synthesis of aminothiazolyl norfloxacin analogues as potential antimicrobial agents and their biological evaluation.

    abstract::A series of aminothiazolyl norfloxacin analogues as a new type of potential antimicrobial agents were synthesized and screened for their antimicrobial activities. Most of the prepared compounds exhibited excellent inhibitory efficiencies. Especially, norfloxacin analogue II-c displayed superior antimicrobial activitie...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.01.072

    authors: Wang LL,Battini N,Bheemanaboina RRY,Zhang SL,Zhou CH

    更新日期:2019-04-01 00:00:00

  • Discovery, optimization and biological evaluation for novel c-Met kinase inhibitors.

    abstract::The c-Met kinase has emerged as an attractive target for developing antitumor agents because of its close relationship with the development of many human cancers, poor clinical outcomes and even drug resistance. A series of novel c-Met kinase inhibitors have been identified with multiple workflow in this work, includi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.11.073

    authors: Yuan H,Liu Q,Zhang L,Hu S,Chen T,Li H,Chen Y,Xu Y,Lu T

    更新日期:2018-01-01 00:00:00

  • Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents.

    abstract::Several members of the phenylamino-1,4-naphthoquinone series were prepared in order to investigate structure-activity relationships (SAR) and to explore the antitumor effects associated with this scaffold. The cytotoxic effects of the aminoquinones (EC50) against a panel of cancer cell lines (MCF7, DU145 and T24 cells...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.10.006

    authors: Benites J,Valderrama JA,Bettega K,Pedrosa RC,Calderon PB,Verrax J

    更新日期:2010-12-01 00:00:00

  • LUMO energy of model compounds of bispyridinium compounds as an index for the inhibition of choline kinase.

    abstract::Eleven derivatives of 1,1'-[1,2-ethylenebis(benzene-1,4-diylmethylene)]bis(4-pyridinium) dibromides bearing various groups at C-4 of the pyridinium moiety were synthesized and examined for their inhibition of choline kinase (ChoK) and antiproliferative activities. The C-4 substituents include electron-releasing, neutr...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(01)01219-3

    authors: Campos J,del Carmen Núñez M,Rodríguez V,Entrena A,Hernández-Alcoceba R,Fernández F,Lacal JC,Gallo MA,Espinosa A

    更新日期:2001-03-01 00:00:00

  • 2,2'-bipyridyl based copper complexes down regulate expression of pro-inflammatory cytokines and suppress MAPKs in mitogen induced Peripheral blood mononuclear cells.

    abstract::2,2'-bipyridyl based copper complex I: [CuC24H22N6O10] at 10 nM and complex Ia: [Cu2C32H43N8O3](PF6)4 at 7 nM exhibited 50% inhibition of lymphocyte proliferation and less than 20% cytotoxicity in peripheral blood mononuclear cells (PBMCs). Further, pro-inflammatory cytokines such as TNF-alpha and IL-1beta and pro-inf...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.01.041

    authors: Rupesh KR,Priya AM,Sundarakrishnan B,Venkatesan R,Lakshmi BS,Jayachandran S

    更新日期:2010-06-01 00:00:00

  • Schiff bases of indoline-2,3-dione (isatin) derivatives and nalidixic acid carbohydrazide, synthesis, antitubercular activity and pharmacophoric model building.

    abstract::Tuberculosis (TB) remains among the world's great public health challenges. Worldwide resurgence of TB is due to two major problems: the AIDS epidemic, which started in the mid-1980s, and the outbreak of multidrug resistant (MDR) TB. Thus, there is an urgent need for anti-TB drugs with enhanced activity against MDR st...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.07.020

    authors: Aboul-Fadl T,Bin-Jubair FA,Aboul-Wafa O

    更新日期:2010-10-01 00:00:00

  • Synthesis and antiviral evaluation of α-L-2'-deoxythreofuranosyl nucleosides.

    abstract::The synthesis of a series of α-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-α-L-threose, involving a Vorbrüggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.05.036

    authors: Toti KS,Derudas M,McGuigan C,Balzarini J,Van Calenbergh S

    更新日期:2011-09-01 00:00:00

  • Design, synthesis and pharmacological evaluation of N4,N6-disubstituted pyrimidine-4,6-diamine derivatives as potent EGFR inhibitors in non-small cell lung cancer.

    abstract::A novel series of 4, 6-disubstituted pyrimidines derivatives were designed, synthesized, and evaluated as epidermal growth factor receptor (EGFR) inhibitors for non-small cell lung cancer(NSCLC). 4, 6-disubstituted pyrimidines as core structure was utilized to substitute the lead structure AZD3759 of the quinazoline b...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.08.031

    authors: Zhang Y,Lv H,Luo L,Xu Y,Pan Y,Wang Y,Lin H,Xiong J,Guo P,Zhang J,Li X,Ye F

    更新日期:2018-09-05 00:00:00

  • Synthesis and biological evaluation of pyrrolo[2,3-b]pyridine analogues as antiproliferative agents and their interaction with calf thymus DNA.

    abstract::A series of thirty two novel pyrrolo[2,3-b]pyridine analogues synthesized, characterized ((1)H NMR, (13)C NMR and MS) and cytotoxic evaluation of these molecules carried out over a panel of three human cancer cell lines including A549 (lung cancer), HeLa (cervical cancer) and MDA MB-231 (breast cancer), using sulforho...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.02.059

    authors: Narva S,Chitti S,Bala BR,Alvala M,Jain N,Kondapalli VG

    更新日期:2016-05-23 00:00:00

  • Discovery of MGS0274, an ester prodrug of a metabotropic glutamate receptor 2/3 agonist with improved oral bioavailability.

    abstract::We previously reported that MGS0008 is a selective group II metabotropic glutamate receptor (mGlu2/3 receptor) agonist that is effective in animal models of schizophrenia. MGS0008 is a highly hydrophilic glutamate analog and is therefore expected to show low oral bioavailability in humans. To improve the oral bioavail...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112521

    authors: Urabe H,Miyakoshi N,Ohtake N,Nozoe A,Ochi M,Fukasawa M,Kinoshita K,Yamaguchi JI,Marumo T,Hikichi H,Chaki S,Hashihayata T

    更新日期:2020-10-01 00:00:00

  • Synthesis of substituted 3-amino-N-phenyl-1H-indazole-1-carboxamides endowed with antiproliferative activity.

    abstract::Several new N-phenyl-1H-indazole-1-carboxamides 1c-h and 4l,m were prepared by reacting phenyl isocyanate derivatives 3a,b with 3-amino-1H-indazole derivatives 2c,e,g or 1H-indazole 2l respectively. Chemical transformations of compounds 1a,b and 1g,h gave 3-acetamido-N-phenyl-1H-indazole-1-carboxamide derivatives 5a,b...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.10.032

    authors: Maggio B,Raimondi MV,Raffa D,Plescia F,Cascioferro S,Plescia S,Tolomeo M,Di Cristina A,Pipitone RM,Grimaudo S,Daidone G

    更新日期:2011-01-01 00:00:00

  • Organometallic compounds in the discovery of new agents against kinetoplastid-caused diseases.

    abstract::The development of safe and affordable antiparasitic agents effective against neglected tropical diseases is a big challenge of the drug discovery. The drugs currently employed have limitations such as poor efficacy, drug resistance or side effects. Thus, the search for new promising drugs is more and more crucial. Me...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2018.05.044

    authors: Ravera M,Moreno-Viguri E,Paucar R,Pérez-Silanes S,Gabano E

    更新日期:2018-07-15 00:00:00

  • Design, synthesis and anticancer potential of NSC-319745 hydroxamic acid derivatives as DNMT and HDAC inhibitors.

    abstract::DNA methyltransferases (DNMTs) and histone deacetylases (HDACs) are important epigenetic targets during anticancer drug development. Recent study indicates that DNMT inhibitors and HDAC inhibitors display synergistic effects in certain cancers, therefore, development of molecules targeting both DNMT and HDAC is of the...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.04.017

    authors: Yuan Z,Sun Q,Li D,Miao S,Chen S,Song L,Gao C,Chen Y,Tan C,Jiang Y

    更新日期:2017-07-07 00:00:00

  • Design, synthesis and docking studies of some novel (R)-2-(4'-chlorophenyl)-3-(4'-nitrophenyl)-1,2,3,5-tetrahydrobenzo[4,5] imidazo [1,2-c]pyrimidin-4-ol derivatives as antitubercular agents.

    abstract::Filamenting temperature-sensitive mutant (FtsZ) is a novel target for the treatment of tuberculosis. A series of (R)-2-(4'-chlorophenyl)-3-(4'-nitrophenyl)-1,2,3,5-tetrahydrobenzo[4,5] imidazo[1,2-c]pyrimidin-4-ol derivatives were designed and docked on the FtsZ protein crystal structure (PDB Id: 1RLU, resolution 2.08...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.06.019

    authors: Barot KP,Jain SV,Gupta N,Kremer L,Singh S,Takale VB,Joshi K,Ghate MD

    更新日期:2014-08-18 00:00:00

  • Novel inhibitors of acetyl- and butyrylcholinesterase derived from the alkaloids dehydroevodiamine and rutaecarpine.

    abstract::Derived from the structures of the alkaloids rutaecarpine and dehydroevodiamine (DHED), and the long-known acetylcholinesterase (AChE) inhibitor tacrine, respectively, novel compounds were synthesised, including: 13-methyl-5,8-dihydro-6H-isoquino[1,2-b]quinazolin-13-ium chloride (12), (8Z)-5,6-dihydro-8H-isoquino[1,2-...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2004.12.003

    authors: Decker M

    更新日期:2005-03-01 00:00:00

  • Pharmacophore-based virtual screening and Bayesian model for the identification of potential human leukotriene A4 hydrolase inhibitors.

    abstract::Leukotriene A4 hydrolase (LTA4H), an enzyme involved in the conversion of LTA4 to LTB4, is an emerging and important anti-inflammatory target. This study demonstrates the development of quantitative pharmacophore hypothesis and Bayesian model and their applications in identification of potential human LTA4H (hLTA4H) i...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.02.007

    authors: Thangapandian S,John S,Sakkiah S,Lee KW

    更新日期:2011-05-01 00:00:00

  • N-alkyl-hydroxybenzoyl anilide hydroxamates as dual inhibitors of HDAC and HSP90, downregulating IFN-γ induced PD-L1 expression.

    abstract::Novel dual inhibitors of histone deacetylase (HDAC) and heat-shock protein 90 (HSP90) are synthesized and evaluated. These compounds are endowed with potent HDAC and HSP90 inhibitory activities with IC50 values in nanomolar range with Compound 20 (HDAC IC50 = 194 nM; HSP90α IC50 = 153 nM) and compound 26 (HDAC IC50 = ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111725

    authors: Mehndiratta S,Lin MH,Wu YW,Chen CH,Wu TY,Chuang KH,Chao MW,Chen YY,Pan SL,Chen MC,Liou JP

    更新日期:2020-01-01 00:00:00

  • Synthesis and DNA-binding studies of two ruthenium(II) complexes of an intercalating ligand.

    abstract::Two new ruthenium(II) complexes [Ru(bpy)(2)(HBT)](2+) (1) and [Ru(phen)(2)(HBT)](2+) (2) (bpy=2,2'-bipyridine; phen=1,10-phenanthroline; HBT=11H, 13H-4, 5,9,10,12,14-hexaaza-benzo [b] triphenylene) have been synthesized and characterized by elemental analysis, mass spectra, (1)H NMR and cyclic voltammetry. The DNA bin...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.10.013

    authors: Lawrence Arockiasamy D,Radhika S,Parthasarathi R,Nair BU

    更新日期:2009-05-01 00:00:00

  • PRODRUGS FOR NITROREDUCTASE BASED CANCER THERAPY- 2: Novel amide/Ntr combinations targeting PC3 cancer cells.

    abstract::The use of nitroreductases (NTR) that catalyze the reduction of nitro compounds by using NAD(P)H in GDEPT (Gene-directed enzyme prodrug therapy) studies which minimize toxicity at healthy cells and increases concentration of drugs at cancer cells is remarkable. Discovery of new prodrug/NTR combinations is necessary to...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.03.035

    authors: Güngör T,Önder FC,Tokay E,Gülhan ÜG,Hacıoğlu N,Tok TT,Çelik A,Köçkar F,Ay M

    更新日期:2019-06-01 00:00:00

  • Synthesis and characterization of novel phosphonocarboxylate inhibitors of RGGT.

    abstract::Phosphonocarboxylate (PC) analogs of the anti-osteoporotic drugs, bisphosphonates, represent the first class of selective inhibitors of Rab geranylgeranyl transferase (RabGGTase, RGGT), an enzyme implicated in several diseases including ovarian, breast and skin cancer. Here we present the synthesis and biological char...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.06.062

    authors: Coxon FP,Joachimiak L,Najumudeen AK,Breen G,Gmach J,Oetken-Lindholm C,Way R,Dunford JE,Abankwa D,Błażewska KM

    更新日期:2014-09-12 00:00:00