pH and DNA luminescence switching, DNA photocleavage and cytotoxic properties of two thiophene-containing ruthenium(II) complexes.

Abstract:

:Two new Ru(II) complexes, [Ru(Htip)3]Cl2 (1) and [Ru(Htip)2(dppz)]Cl2 (2), were synthesised and were characterised. The ground- and excited-state acid-base properties of 1 and 2 were studied and demonstrated that 1 acted as a pH-induced "on-off-on" luminescence switch. The binding behaviours of 1 and 2 to calf thymus DNA were studied with absorption and emission spectroscopy, DNA viscosities and density functional theory calculations. 2 was found to act as a DNA molecular light switch and as an efficient photocleaver of pUC 18 DNA. The cytotoxicities of the complexes were evaluated with the MTT method and it was found that 1 displayed apparent anticancer activity against MCF-7 cell, whereas 2 exhibited more potent and wider-spectrum antitumor activities against all cancer cell lines tested.

journal_name

Eur J Med Chem

authors

Zhao XL,Li ZS,Zhang AG,Liu P,Song XM,Wang KZ

doi

10.1016/j.ejmech.2014.09.041

subject

Has Abstract

pub_date

2014-11-24 00:00:00

pages

10-22

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(14)00859-9

journal_volume

87

pub_type

杂志文章
  • Design, synthesis and antitubercular evaluation of novel series of N-[4-(piperazin-1-yl)phenyl]cinnamamide derivatives.

    abstract::The analogs of N-[4-(piperazin-1-yl)phenyl]cinnamamide were designed and synthesized by molecular hybridization approach in which part C of the designed molecule was linked through amide and carbamate functionality that improves the physicochemical properties and govern the pharmacokinetic and pharmacodynamic behavior...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.01.024

    authors: Patel KN,Telvekar VN

    更新日期:2014-03-21 00:00:00

  • Oxindole: A chemical prism carrying plethora of therapeutic benefits.

    abstract::Oxindole has emerged as a valuable scaffold in medicinal chemistry possessing diverse range of pharmacological activities. Its value has further been increased by its natural occurrence as alkaloids in variety of plants. It was first extracted from the cat claw's plant Uncaria tomentosa found in the Amazon rainforest ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2016.08.011

    authors: Kaur M,Singh M,Chadha N,Silakari O

    更新日期:2016-11-10 00:00:00

  • Platinated benzonaphthyridone is a stronger inhibitor of poly(ADP-ribose) polymerase-1 and a more potent anticancer agent than is the parent inhibitor.

    abstract::Inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1) have shown to be promising in clinical trials against cancer and other diseases, and lots of efforts have been put into the development of organic compounds as more potent PARP-1 inhibitors. Here we describe a strategy to conveniently obtain metal-based PARP-1 inhib...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.10.062

    authors: Wang B,Qian H,Yiu SM,Sun J,Zhu G

    更新日期:2014-01-01 00:00:00

  • Synthesis and biological evaluation of novel alkylated polyamine analogues as potential anticancer agents.

    abstract::A new class of polyamine analogues modified by alkylation at the terminal of the polyamine chain has been synthesized and their structures were determined by 1H NMR, 13C NMR, ESI-MS and elemental analysis. As the representative compound, 3f displayed a broad spectrum of anti-cancer effects by MTT assays. Tumor xenogra...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.10.069

    authors: Li M,Wang Y,Ge C,Chang L,Wang C,Tian Z,Wang S,Dai F,Zhao L,Xie S

    更新日期:2018-01-01 00:00:00

  • Mastering tricyclic ring systems for desirable functional cannabinoid activity.

    abstract::There is growing interest in using cannabinoid receptor 2 (CB2) agonists for the treatment of neuropathic pain and other indications. In continuation of our ongoing program aiming for the development of new small molecule cannabinoid ligands, we have synthesized a novel series of carbazole and γ-carboline derivatives....

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.09.038

    authors: Petrov RR,Knight L,Chen SR,Wager-Miller J,McDaniel SW,Diaz F,Barth F,Pan HL,Mackie K,Cavasotto CN,Diaz P

    更新日期:2013-11-01 00:00:00

  • Synthesis and anticancer activity of 6-heteroarylcoumarins.

    abstract::A series of novel 7-hydroxy-8-methyl-coumarins with indole, pyrimidine, pyrazole, pyran, tetrazolo[1,5-a]pyrimidine, pyrimido[1,2-a]benzimidazol, 2-oxo-1,2-dihydropyridine and dihydropyrazolo[3,4-b]pyridine moieties at C6 position of heterocyclic core have been synthesized. Anticancer activity screening on NCI60 cell ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.10.021

    authors: Galayev O,Garazd Y,Garazd M,Lesyk R

    更新日期:2015-11-13 00:00:00

  • Synthesis and biological evaluation of novel aliphatic amido-quaternary ammonium salts for anticancer chemotherapy: part II.

    abstract::A series of novel aliphatic amido-quaternary ammonium salts were synthesized and evaluated for their anticancer effects involving induction of RhoB. Most of these compounds, featuring open-ring forms of aliphatic amido-quaternary ammonium salts, exhibited potent anti-proliferative activities in human cancer cell lines...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.12.063

    authors: Yang JS,Song D,Ko WJ,Kim B,Kim BK,Park SK,Won M,Lee K,Lee K,Kim HM,Han G

    更新日期:2013-05-01 00:00:00

  • Quinazoline derivatives as selective CYP1B1 inhibitors.

    abstract::CYP1B1 is implicated to have a role in the development of breast, ovarian, renal, skin and lung carcinomas. It has been suggested that identification of potent and specific CYP1B1 inhibitors can lead to a novel treatment of cancer. Flavonoids have a compact rigid skeleton which fit precisely within the binding cavity ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.02.032

    authors: Mohd Siddique MU,McCann GJ,Sonawane VR,Horley N,Gatchie L,Joshi P,Bharate SB,Jayaprakash V,Sinha BN,Chaudhuri B

    更新日期:2017-04-21 00:00:00

  • Synthesis and serotonergic activity of variously substituted (3-amido)phenylpiperazine derivatives and benzothiophene-4-piperazine derivatives: novel antagonists for the vascular 5-HT1B receptor.

    abstract::The synthesis and vascular 5-HT(1B) receptor activity of a novel series of substituted 3-amido phenylpiperazine and 4-(4-methyl-1-piperazinyl)-1-benzo[b]thiophene derivatives is described. Modifications to the amido linked sidechains of the 3-amidophenyl-piperazine derivatives and to the 2-sidechain of the 1-benzo[b]t...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2003.12.008

    authors: Moloney GP,Garavelas A,Martin GR,Maxwell M,Glen RC

    更新日期:2004-04-01 00:00:00

  • N-Aryl-N'-(chroman-4-yl)ureas and thioureas display in vitro anticancer activity and selectivity on apoptosis-resistant glioblastoma cells: screening, synthesis of simplified derivatives, and structure-activity relationship analysis.

    abstract::A series of chroman derivatives previously reported as potassium channel openers, as well as some newly synthesized simplified structures, were examined for their in vitro effects on the growth of three human high-grade glioma cell lines: U373, T98G, and Hs683. Significant in vitro growth inhibitory activity was obser...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.06.050

    authors: Goffin E,Lamoral-Theys D,Tajeddine N,de Tullio P,Mondin L,Lefranc F,Gailly P,Rogister B,Kiss R,Pirotte B

    更新日期:2012-08-01 00:00:00

  • Synthesis and pharmacological evaluation of 2(3H)-furanones and 2(3H)-pyrrolones, combining analgesic and anti-inflammatory properties with reduced gastrointestinal toxicity and lipid peroxidation.

    abstract::A series of 3-arylidene-5-(4-chloro-phenyl)-2(3H)-furanones (2-13) and their nitrogen analogues 1-benzylpyrrolones (14-18) were synthesized. The compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation actions. Some of the newly synthesized compounds showed good anti-inflamma...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.10.030

    authors: Alam MM,Husain A,Hasan SM,Suruchi,Anwer T

    更新日期:2009-06-01 00:00:00

  • Design, synthesis and structure-activity relationship of phthalimides endowed with dual antiproliferative and immunomodulatory activities.

    abstract::The present work reports the synthesis and evaluation of the antitumour and immunomodulatory properties of new phthalimides derivatives designed to explore molecular hybridization and bioisosterism approaches between thalidomide, thiosemicarbazone, thiazolidinone and thiazole series. Twenty-seven new molecules were as...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.04.041

    authors: Cardoso MV,Moreira DR,Oliveira Filho GB,Cavalcanti SM,Coelho LC,Espíndola JW,Gonzalez LR,Rabello MM,Hernandes MZ,Ferreira PM,Pessoa C,Alberto de Simone C,Guimarães ET,Soares MB,Leite AC

    更新日期:2015-01-01 00:00:00

  • Novel nonsteroidal ligands with high binding affinity and potent functional activity for the androgen receptor.

    abstract::While nonsteroidal androgen receptor (AR) antagonists have been known for many years, and used in the clinic for the treatment of hormone dependent prostate cancer, very little is known about nonsteroidal AR agonists. We designed and synthesized a series of chiral bicalutamide analogs, which bear electron-withdrawing ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(02)01335-1

    authors: He Y,Yin D,Perera M,Kirkovsky L,Stourman N,Li W,Dalton JT,Miller DD

    更新日期:2002-08-01 00:00:00

  • New and efficient approach for synthesis of novel bioactive [1,3,4]thiadiazoles incorporated with 1,3-thiazole moiety.

    abstract::A series of novel 1,3,4-thiadiazoles incorporated with thiazole moiety was synthesized by reaction of 5-acetyl-2-benzoylimino-3-phenyl-1,3,4-thiadiazole thiosemicarbazone 2 with each of N-phenyl 2-oxo-propanehydrazonoyl chloride 3 and ethyl (N-aryl-hydrazono) chloroacetate 5 in dioxane in basic medium. Also, another s...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.05.009

    authors: Farghaly TA,Abdallah MA,Masaret GS,Muhammad ZA

    更新日期:2015-06-05 00:00:00

  • Synthesis of heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors: effects on the inhibitory activity of the replacement of the cyclopentene central core with pyrazole, thiophene or isoxazole ring.

    abstract::Several heteroaromatic analogues of (2-aryl-1-cyclopentenyl-1-alkylidene)-(arylmethyloxy)amine COX-2 inhibitors, in which the cyclopentene moiety was replaced by pyrazole, thiophene or isoxazole ring, were synthesized, in order to verify the influence of the different nature of the central core on the COX inhibitory p...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(02)01448-4

    authors: Balsamo A,Coletta I,Guglielmotti A,Landolfi C,Mancini F,Martinelli A,Milanese C,Minutolo F,Nencetti S,Orlandini E,Pinza M,Rapposelli S,Rossello A

    更新日期:2003-02-01 00:00:00

  • The conversion of oridonin to spirolactone-type or enmein-type diterpenoid: synthesis and biological evaluation of ent-6,7-seco-oridonin derivatives as novel potential anticancer agents.

    abstract::Starting from commercial available natural product oridonin (1), a practical synthesis of ent-6,7-seco-oridonin derivatives (2, 3, 5, and 9) was accomplished and their biological activities were evaluated. The conversion of spirolactone-type diterpenoid to enmein-type was first completed. The results demonstrated that...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.03.024

    authors: Wang L,Li D,Xu S,Cai H,Yao H,Zhang Y,Jiang J,Xu J

    更新日期:2012-06-01 00:00:00

  • Synthesis, molecular modeling and biological evaluation of 2-(benzylthio)-5-aryloxadiazole derivatives as anti-tumor agents.

    abstract::A series of 2-(benzylthio)-5-aryloxadiazole derivatives have been designed and synthesized, and their biological activities are also evaluated for EGFR inhibitory activity. Fourteen compounds among the twenty compounds are reported for the first time. Their chemical structures are characterized by (1)H NMR, MS, and el...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.11.015

    authors: Liu K,Lu X,Zhang HJ,Sun J,Zhu HL

    更新日期:2012-01-01 00:00:00

  • A pentanoic acid derivative targeting matrix metalloproteinase-2 (MMP-2) induces apoptosis in a chronic myeloid leukemia cell line.

    abstract::Depending on our previous observations, some compounds of pentanoic acid were designed and synthesized. Characterization of the synthesized compounds was done by mass, NMR and IR spectroscopy as well as elemental analysis. Among the synthesized molecules, (2S)-5-oxo-2-[(nitrobenzene-4-yl sulfonyl) amino]-5-(pentylamin...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.09.052

    authors: Mukherjee A,Adhikari N,Jha T

    更新日期:2017-12-01 00:00:00

  • Synthesis and evaluation of a small library of graftable thrombin inhibitors derived from (L)-arginine.

    abstract::Novel piperazinyl-amide derivatives of N-alpha-(aryl-sulfonyl)-L-arginine were synthesized as graftable thrombin inhibitors, in the context of biomaterials' design. The possible disturbance of biological activity due to a variable spacer-arm fixed on the N-4 piperazinyl position and the introduction of a trifluorometh...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.07.010

    authors: Salvagnini C,Gharbi S,Boxus T,Marchand-Brynaert J

    更新日期:2007-01-01 00:00:00

  • Highly potent non-steroidal FXR agonists protostane-type triterpenoids: Structure-activity relationship and mechanism.

    abstract::Farnesoid X receptor (FXR) is a key regulator in charge of bile acid synthesis, transport, and metabolism. Activation of FXR represses bile acid synthesis and increases its excretion and transport, consequently protecting the liver functions. Thus, FXR is considered as a critical therapeutic target of cholestasis and ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111652

    authors: Luan ZL,Huo XK,Dong PP,Tian XG,Sun CP,Lv X,Feng L,Ning J,Wang C,Zhang BJ,Ma XC

    更新日期:2019-11-15 00:00:00

  • Green synthesis and antimicrobial evaluation of some new trifluoromethyl-substituted hexahydropyrimidines by grinding.

    abstract::A series of trifluoromethyl-substituted hexahydropyrimidine derivatives were efficiently synthesized in excellent yields via one-pot three-component reaction of aromatic aldehydes, ethyl trifluoroacetoacetate and thiourea(urea) in presence of p-toluenesulfonic acid under solvent-free conditions at room temperature by ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.09.036

    authors: Zohdi HF,Rateb NM,Elnagdy SM

    更新日期:2011-11-01 00:00:00

  • Synthesis and antimicrobial activities of a new series of 4-S-[4(1)-amino-5(1)-oxo-6(1)-substituted benzyl-4(1),5(1)-dihydro-1(1),2(1),4(1)-triazin-3-yl]mercaptoacetyl-3-arylsydnones.

    abstract::The synthesis of some 4-S-(4(1)-amino-5(1)-oxo-6(1)-substituted benzyl-4(1),5(1)-dihydro-1(1),2(1),4(1)-triazin-3-yl)mercaptoacetyl-3-arylsydnones by the reaction of 3-aryl-4-bromoacetylsydnones with 6-substituted-4-amino-3-mercapto-1,2,4-triazin-5-ones is described. The IR, (1)H NMR, mass spectra and elemental analys...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.02.003

    authors: Hegde JC,Girisha KS,Adhikari A,Kalluraya B

    更新日期:2008-12-01 00:00:00

  • Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteria.

    abstract::Herein, we report the synthesis and characterization of new amphiphilic phthalocyanines (Pcs), the study of their singlet oxygen generation capabilities, and biological assays to determine their potential as photosensitizers for photodynamic inactivation of bacteria. In particular, Pcs with an ABAB geometry (where A a...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111957

    authors: Revuelta-Maza MÁ,González-Jiménez P,Hally C,Agut M,Nonell S,de la Torre G,Torres T

    更新日期:2020-02-01 00:00:00

  • Selective apoptosis-inducing activity of synthetic hydrocarbon-stapled SOS1 helix with d-amino acids in H358 cancer cells expressing KRASG12C.

    abstract::Lung cancer is one of the most malignant tumors with the highest morbidity and mortality. Most of them are non-small cell lung cancer (NSCLC). KRASG12C gene mutation is an important driving factor for NSCLC. However, the development of high-affinity inhibitors targeting KRASG12C mutants remains a daunting challenge. H...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111844

    authors: Xu LL,Li CC,An LY,Dai Z,Chen XY,You QD,Hu C,Di B

    更新日期:2020-01-01 00:00:00

  • ANN-QSAR model for selection of anticancer leads from structurally heterogeneous series of compounds.

    abstract::Developing a model for predicting anticancer activity of any classes of organic compounds based on molecular structure is very important goal for medicinal chemist. Different molecular descriptors can be used to solve this problem. Stochastic molecular descriptors so-called the MARCH-INSIDE approach, shown to be very ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.11.016

    authors: González-Díaz H,Bonet I,Terán C,De Clercq E,Bello R,García MM,Santana L,Uriarte E

    更新日期:2007-05-01 00:00:00

  • Ni(II) curcumin complexes for cellular imaging and photo-triggered in vitro anticancer activity.

    abstract::Nickel(II) complexes [Ni(cur)(L)2](OAc) (1-3) where L is N,N-donor heterocyclic bases namely 1,10-phenanthroline (phen in 1), dipyrido[3,2-d:2',3'-f]quinoxaline (dpq in 2), dipyrido[3,2-a:2',3'-c]phenazine (dppz in 3) and Hcur is curcumin were prepared, fully characterized and light-induced in vitro anticancer activit...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112632

    authors: Banaspati A,Raza MK,Goswami TK

    更新日期:2020-10-15 00:00:00

  • Single-molecule chemiluminescent photosensitizer for a self-activating and tumor-selective photodynamic therapy of cancer.

    abstract::While photodynamic therapy is known for significant advantages over conventional cancer therapies, its dependence on light has limited it to treating tumors on or just under the skin or on the outer lining of organs/cavities. Herein, we have developed a single-molecule photosensitizer capable of intracellular self-act...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111683

    authors: Pinto da Silva L,Núnez-Montenegro A,Magalhães CM,Ferreira PJO,Duarte D,González-Berdullas P,Rodríguez-Borges JE,Vale N,Esteves da Silva JCG

    更新日期:2019-12-01 00:00:00

  • Synthesis of C- and O-prenylated tetrahydroxystilbenes and O-prenylated cinnamates and their action towards cancer cells.

    abstract::Synthesis of the naturally occurred C- and O-prenylated tetrahydroxystilbenes and O-prenylated cinnamates was carried out by decarbonylative Heck reaction and selenium dioxide catalysed oxidation, respectively. In the decarbonylative Heck synthetic route, fusion of benzoyl chloride and styrene derivatives was catalyse...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.02.017

    authors: Koolaji N,Abu-Mellal A,Tran VH,Duke RK,Duke CC

    更新日期:2013-05-01 00:00:00

  • Synthesis and antibacterial activity of novel modified 5-O-mycaminose 14-membered ketolides.

    abstract::A practicable method of introducing a side chain to the C-4' position of 5-O-desosamine in the 14-membered ketolides was developed. And using this method, a series of novel modified 5-O-mycaminose ketolides were synthesized. These ketolides containing 5-O-4'-carbamate mycaminose were evaluated for their in vitro antib...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.08.023

    authors: Xu Y,Chen X,Zhu D,Liu Y,Zhao Z,Jin L,Liu C,Lei P

    更新日期:2013-11-01 00:00:00

  • Lipophilicity-antiproliferative activity relationship study leads to the preparation of a ruthenium(II) arene complex with considerable in vitro cytotoxicity against cancer cells and a lower in vivo toxicity in zebrafish embryos than clinically approved c

    abstract::Ru(II)-arene complexes are attracting increasing attention due to their considerable antitumoral activity. However, it is difficult to clearly establish a direct relationship between their structure and antiproliferative activity, as substantial structural changes might not only affect their anticancer activity but al...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.03.029

    authors: Haghdoost M,Golbaghi G,Létourneau M,Patten SA,Castonguay A

    更新日期:2017-05-26 00:00:00