当前位置： SCI文献检索 > BIOORGANIC CHEMISTRY期刊下所有文献 > Discovery of novel cathepsin inhibitors with potent anti-metastatic effects in breast cancer cells.

Discovery of novel cathepsin inhibitors with potent anti-metastatic effects in breast cancer cells.

Abstract：

:It is still challenging to determine the potential targets of natural products, which is essential for further drug research and development. Due to its novel mechanism of action of inducing autophagy effects in breast cancer cells, asperphenamate has received our considerable attention. However, its unknown target inevitably impedes further study. In our previous work, the target enzyme of asperphenamate was predicted as cathepsin by the natural product consensus pharmacophore strategy. Then, asperphenamate and its three derivatives were chosen to study in detail by molecular docking calculations with AutoDock 4 suite. The docking results showed the three derivatives interacted more tightly with either cathepsin L or cathepsin S than with asperphenamate. The ortho-benzyloxyl phenylacetyl derivative 1 andp-toluenesulfonyl derivative 3 showed similar interactions with cathepsin L and adopted a better geometric shape within the binding pocket than did the N-CBZ-piperidyl analog 2. On the other hand, compound 2 formed more hydrogen bonds than 1 and 3 to make it tightly bind within cathepsin S. The cathepsin inhibitory activity assay verified the molecular simulation results. Compound 2 was remarkably less active than 1 and 3 against cathepsin L. However, compound 2 showed the strongest potency against cathepsin S with IC50 of 13.12 ± 0.29 μM. Considering that cathepsin S plays a vital role in the process of metastasis in breast cancer cells, the inhibitory effect of 2 on migration and invasion was further studied in human breast cancer MDA-MB-231 cells by wound healing and transwell chamber assays. The results illustrated that 2 exhibited an apparent inhibitory ability to the metastasis of MDA-MB-231 cells. Next, 2 will be chosen as a lead compound to develop novel double functional chemotherapeutic agents with both novel mechanisms of action against apoptosis-resistant cancer cells, such as inducing autophagy and inhibiting cancer metastasis.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Yuan L,Sheng L,He W,Zou C,Hu B,Liu J,Ge W,Liu Y,Wang J,Ma E

doi

10.1016/j.bioorg.2018.09.029

subject

Has Abstract

pub_date

2018-12-01 00:00:00

pages

672-680

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(18)30790-9

journal_volume

81

pub_type

杂志文章

相关文献

BIOORGANIC CHEMISTRY文献大全
  • 1-(4-Methane(amino)sulfonylphenyl)-3-(4-substituted-phenyl)-5-(4-trifluoromethylphenyl)-1H-2-pyrazolines/pyrazoles as potential anti-inflammatory agents.

    abstract：:2-Pyrazolins 14a-l and pyrazoles 15a-l were designed as celecoxib analogs for the evaluation of their in vitro COX-1/COX-2 inhibitory activity and the in vivo anti-inflammatory activity. Compounds 14i, 15a, 15d and 15f were the most COX-2 selective derivatives (S.I.=5.93, 6.08, 5.03 and 5.27 respectively) while the py...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2015.09.002

    authors： Abdellatif KR,Elshemy HA,Azoz AA

    更新日期：2015-12-01 00:00:00

  • Identification of human, rat and mouse hydrolyzing enzymes bioconverting amino acid ester prodrug of ketoprofen.

    abstract：:Alkyl ester prodrugs are well known to be bioconverted by carboxylesterases, particularly in rodents' by first-pass metabolism in the systemic circulation and liver. However, the bioconversion of structurally more complex esters with polar functional groups is less well understood, especially in humans. Therefore, it ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.09.018

    authors： Huttunen KM

    更新日期：2018-12-01 00:00:00

  • Synthesis of a novel series of (Z)-3,5-disubstituted thiazolidine-2,4-diones as promising anti-breast cancer agents.

    abstract：:A novel series of (Z)-3,5-disubstituted thiazolidine-2,4-diones 4-16 has been designed and synthesized. Preliminary screening of these compounds for their anti-breast cancer activity revealed that compounds 5, 7, and 9 possess the highest anti-cancer activities. The anti-tumor effects of compounds 5, 7, and 9 were eva...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.103569

    authors： El-Kashef H,Badr G,Abo El-Maali N,Sayed D,Melnyk P,Lebegue N,Abd El-Khalek R

    更新日期：2020-03-01 00:00:00

  • Design, synthesis, and anticancer activity of imidazo[2,1-b]oxazole-based RAF kinase inhibitors.

    abstract：:In the present work, a novel series of B-RAF kinase inhibitors having imidazo[2,1-b]oxazole scaffold was designed and synthesized based on the structures of the well-known B-RAF inhibitors. The twenty two final compounds were tested over A375 and SKMEL28 cell lines to determine the primary cytotoxic activity of these ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103349

    authors： Abdel-Maksoud MS,Ammar UM,El-Gamal MI,Gamal El-Din MM,Mersal KI,Ali EMH,Yoo KH,Lee KT,Oh CH

    更新日期：2019-12-01 00:00:00

  • Bioactive monoterpene indole alkaloids from Nauclea officinalis.

    abstract：:Two new monoterpene indole alkaloids, naucleaoffines A (1) and B (2), together with six known alkaloids (3-8), were isolated from the stems and leaves of Nauclea officinalis. The structures of 1 and 2 were elucidated by extensive spectroscopic methods and the known compounds were identified by comparisons with the dat...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.10.013

    authors： Liu YP,Liu QL,Zhang XL,Niu HY,Guan CY,Sun FK,Xu W,Fu YH

    更新日期：2019-03-01 00:00:00

  • Spectroscopic investigation of the interaction of water-soluble azocalix[4]arenes with bovine serum albumin.

    abstract：:In this work, three hydrosoluble azocalix[4]arene derivatives, 5-(o-methylphenylazo)-25,26,27-tris(carboxymethoxy)-28-hydroxycalix[4]arene (o-MAC-Calix), 5-(m-methylphenylazo)-25,26,27-tris(carboxymethoxy)-28-hydroxycalix[4]arene (m-MAC-Calix) and 5-(p-methylphenylazo)-25,26,27-tris(carboxymethoxy)-28-hydroxycalix[4]a...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2014.12.002

    authors： Fan P,Wan L,Shang Y,Wang J,Liu Y,Sun X,Chen C

    更新日期：2015-02-01 00:00:00

  • Design, synthesis, in vitro and in silico investigation of aldose reductase inhibitory effects of new thiazole-based compounds.

    abstract：:Aldose reductase (AR) catalyzes the NADPH-dependent reduction of glucose to sorbitol in the polyol pathway, which plays an important role in the development of diabetic complications including cataract, retinopathy, nephropathy, and neuropathy. AR has been considered as an important target to heal these long-term diab...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104110

    authors： Sever B,Altıntop MD,Demir Y,Akalın Çiftçi G,Beydemir Ş,Özdemir A

    更新日期：2020-09-01 00:00:00

  • Withanolides from Physalis peruviana showing nitric oxide inhibitory effects and affinities with iNOS.

    abstract：:A phytochemical study to obtain new nitric oxide (NO) inhibitors resulted in the isolation of five new withanolides from the whole plants of Physalis peruviana. The structures were determined on the basis of extensive NMR spectroscopic data analysis as well as the time-dependent density functional theory (TDDFT) elect...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.03.051

    authors： Dong B,An L,Yang X,Zhang X,Zhang J,Tuerhong M,Jin DQ,Ohizumi Y,Lee D,Xu J,Guo Y

    更新日期：2019-06-01 00:00:00

  • Synthesis and biological evaluation of new bis-indolone-N-oxides.

    abstract：:A series of bis-indolone-N-oxides, 1a-f, was prepared from bis(ethynyl)benzenes and o-halonitroaryls and studied for their in vitro antiplasmodial activities against Plasmodium falciparum and representative strains of bacteria and candida as well as for their cytotoxicity against a human tumor cell line (MCF7). They d...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2013.03.001

    authors： Najahi E,Valentin A,Téné N,Treilhou M,Nepveu F

    更新日期：2013-06-01 00:00:00

  • Synthesis, biological evaluation and molecular docking studies of bis-chalcone derivatives as xanthine oxidase inhibitors and anticancer agents.

    abstract：:In this study, a series of B-ring fluoro substituted bis-chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and evaluated for their ability to inhibit xanthine oxidase (XO) and growth inhibitory activity against MCF-7 and Caco-2 human cancer cell lines, in vitro. According to the results o...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103149

    authors： Burmaoglu S,Ozcan S,Balcioglu S,Gencel M,Noma SAA,Essiz S,Ates B,Algul O

    更新日期：2019-10-01 00:00:00

  • Synthesis of pyrimidine-2,4,6-trione derivatives: Anti-oxidant, anti-cancer, α-glucosidase, β-glucuronidase inhibition and their molecular docking studies.

    abstract：:This paper describes a facile protocol, efficient, and environmentally benign for the synthesis a series of barbiturate acid substituted at C5 position 3a-o. The desired compounds subjected in vitro for different set of bioassays including against anti-oxidant (DPPH and super oxide scavenger assays), anti-cancer, α-gl...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2016.07.009

    authors： Barakat A,Islam MS,Al-Majid AM,Ghabbour HA,Yousuf S,Ashraf M,Shaikh NN,Iqbal Choudhary M,Khalil R,Ul-Haq Z

    更新日期：2016-10-01 00:00:00

  • Esterification of all four monoribonucleotides with acetyl-D-L-valine proceeds with a preference for the D-isomer but the D/L ratio in the products declines as a function of the hydrophobicity of the nucleotide.

    abstract：:We recently reported that esterification of 5'-AMP with N-acetyl amino acids proceeds with a preference for D-amino acids, and the D/L ratio in products declines as the hydrophobicity of the amino acid declines. Using one amino acid, Ac-Val, we now show that esterification of all four nucleotides proceeds with a pref...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/0045-2068(92)90019-y

    authors： Wickramasinghe NS,Lacey JC Jr

    更新日期：1992-01-01 00:00:00

  • Heterocyclic cellular lipid peroxidation inhibitors inspired by the marine antioxidant barettin.

    abstract：:The marine environment remains a rich source for the discovery and development of novel bioactive compounds. The present paper describes the design, synthesis and biological evaluation of a library of small molecule heterocyclic mimetics of the marine 2,5-diketopiperazine barettin which is a powerful natural antioxida...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.11.024

    authors： Labrière C,Andersen JH,Albrigtsen M,Hansen JH,Svenson J

    更新日期：2019-03-01 00:00:00

  • Expeditious and eco-friendly synthesis of new multifunctionalized pyrrole derivatives and evaluation of their antioxidant property.

    abstract：:Diminution of oxidative stress-mediated diseases is an essential pharmaceutical objective in modern biomedical research. The present work stresses upon the efficient and eco-friendly synthesis of an array of novel diversely functionalized pyrrole derivatives which are found to be antioxidants with reactive oxygen spec...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.103734

    authors： Kundu T,Pramanik A

    更新日期：2020-05-01 00:00:00

  • Design, synthesis and anti-diabetic activity of triazolotriazine derivatives as dipeptidyl peptidase-4 (DPP-4) inhibitors.

    abstract：:Type 2 diabetes mellitus (T2DM) is one of the major global metabolic disorders characterized by insulin resistance and chronic hyperglycemia. Inhibition of the enzyme, dipeptidyl peptidase-4 (DPP-4) has been proved as successful and safe therapy for the treatment of T2DM since last decade. In order to design novel DPP...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2017.03.004

    authors： Patel BD,Bhadada SV,Ghate MD

    更新日期：2017-06-01 00:00:00

  • Ursolic and oleanolic acid derivatives with cholinesterase inhibiting potential.

    abstract：:Triterpenoids are in the focus of scientific interest, and they were evaluated for many pharmacological applications among them their ability to act as inhibitors of cholinesterases. These inhibitors are still of interest as drugs that improve the life quality of patients suffering from age-related dementia illnesses ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.12.013

    authors： Loesche A,Köwitsch A,Lucas SD,Al-Halabi Z,Sippl W,Al-Harrasi A,Csuk R

    更新日期：2019-04-01 00:00:00

  • A novel bi-functional chalcone inhibits multi-drug resistant Staphylococcus aureus and potentiates the activity of fluoroquinolones.

    abstract：:Staphylococcus aureus is the leading cause of bacteraemia and the dwindling supply of effective antibacterials has exacerbated the problem of managing infections caused by this bacterium. Isoliquiritigenin (ISL) is a plant flavonoid that displays therapeutic potential against S. aureus. The present study identified a ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.10.024

    authors： Gupta VK,Gaur R,Sharma A,Akther J,Saini M,Bhakuni RS,Pathania R

    更新日期：2019-03-01 00:00:00

  • Interaction of C20-substituted derivative of pregnenolone acetate with copper (II) leads to ROS generation, DNA cleavage and apoptosis in cervical cancer cells: Therapeutic potential of copper chelation for cancer treatment.

    abstract：:Cervical cancer is a leading cause of cancer-related deaths among women in developing countries. Therefore, development of new chemotherapeutic agents is required. Unlike normal cells, cancer cells contain elevated copper levels which play an integral role in angiogenesis. Thus, targeting copper via copper-specific ch...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.03.031

    authors： Zafar A,Singh S,Ahmad S,Khan S,Imran Siddiqi M,Naseem I

    更新日期：2019-06-01 00:00:00

  • Design, synthesis and photoinduced DNA cleavage studies of [1,2,4]-triazolo[4,3-a]quinoxalin-4(5H)-ones.

    abstract：:An expedient and eco-friendly synthesis of 1-aryl/heteroaryl-[1,2,4]-triazolo[4,3-a]quinoxalin-4(5H)-ones (4) has been accomplished via iodobenzene diacetate mediated oxidative intramolecular cyclization of 3-(2-(aryl/heteroarylidene)hydrazinyl)-quinoxalin-2(1H)-ones (3). Ten synthesized compounds 3 and 4 (10-40 μg) o...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.102932

    authors： Sumran G,Aggarwal R,Mittal A,Aggarwal A,Gupta A

    更新日期：2019-07-01 00:00:00

  • Recent advancement in the discovery and development of COX-2 inhibitors: Insight into biological activities and SAR studies (2008-2019).

    abstract：:Cyclooxygenase-2 is a very important physiological enzyme playing key roles in various biological functions especially in the mechanism of pain and inflammation, among other roles, making it a molecule of high interest to the pharmaceutical community as a target. COX 2 enzyme is induced only during inflammatory proces...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.bioorg.2019.103007

    authors： Sharma V,Bhatia P,Alam O,Javed Naim M,Nawaz F,Ahmad Sheikh A,Jha M

    更新日期：2019-08-01 00:00:00

  • A novel amino cellulose derivative using ATRP method: Preparation, characterization, and investigation of its antibacterial activity.

    abstract：:In this study, we prepared a novel amino cellulose derivative (benzyl cellulose-g-poly [2-(N,N-Dimethylamino)ethyl methacrylate]) via a homogeneous ATRP method. The successful synthesis of the novel amino cellulose was confirmed by FT-IR and 1H NMR. This study addressed the different characteristics of the prepared po...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104355

    authors： Shokri M,Moradi S,Amini S,Shahlaei M,Seidi F,Saedi S

    更新日期：2021-01-01 00:00:00

  • Kinetic Isotope Effects and Stereochemical Studies on a Ribonuclease Model: Hydrolysis Reactions of Uridine 3'-Nitrophenyl Phosphate.

    abstract：:The reactions of a ribonuclease model substrate, the compound uridine-3'-p-nitrophenyl phosphate, have been examined using heavy-atom isotope effects and stereochemical analysis. The cyclization of this compound is subject to catalysis by general base (by imidazole buffer), specific base (by carbonate buffer), and by ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1006/bioo.2000.1170

    authors： Hengge AC,Bruzik KS,Tobin AE,Cleland WW,Tsai MD

    更新日期：2000-06-01 00:00:00

  • Separation and configurational assignment of stereoisomeric phenalenones from the marine mangrove-derived fungus Penicillium herquei MA-370.

    abstract：:Eight phenalenone derivatives, including four new compounds, aceneoherqueinones A and B (1 and 2), (+)-aceatrovenetinone A (3a), and (+)-aceatrovenetinone B (3d), along with four known congeners, (-)-aceatrovenetinone A (3b), (-)-aceatrovenetinone B (3c), (-)-scleroderolide (4a), and (+)-scleroderolide (4b), were char...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104477

    authors： Yang SQ,Mándi A,Li XM,Liu H,Li X,Balázs Király S,Kurtán T,Wang BG

    更新日期：2021-01-01 00:00:00

  • Synthesis, cytotoxic evaluation, and molecular docking studies of novel quinazoline derivatives with benzenesulfonamide and anilide tails: Dual inhibitors of EGFR/HER2.

    abstract：:We synthesized a new series of 2-[(3-(4-sulfamoylphenethyl)-4(3H)-quinazolinon-2-yl)thio]anilide derivatives (2-16) and evaluated their cytotoxic activity against breast adenocarcinoma (MCF-7), colorectal adenocarcinoma (HT-29), and acute myeloid leukemia (HL-60 and K562) cells. To reveal their selectivity toward canc...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103461

    authors： Alkahtani HM,Abdalla AN,Obaidullah AJ,Alanazi MM,Almehizia AA,Alanazi MG,Ahmed AY,Alwassil OI,Darwish HW,Abdel-Aziz AA,El-Azab AS

    更新日期：2020-01-01 00:00:00

  • Design, synthesis and pharmacological evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents.

    abstract：:Two series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 2,4-imidazolinedione/pyrazolone scaffold were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against HT-29, H460, A549, MKN-45, and U87MG cancer cell lines in vitro. The pharmacological data indicated that mo...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2014.07.011

    authors： Zhou S,Ren J,Liu M,Ren L,Liu Y,Gong P

    更新日期：2014-12-01 00:00:00

  • The green synthesis and molecular docking of novel N-substituted rhodanines as effective inhibitors for carbonic anhydrase and acetylcholinesterase enzymes.

    abstract：:Recently, inhibition effects of enzymes such as acetylcholinesterase (AChE) and carbonic anhydrase (CA) has appeared as a promising approach for pharmacological intervention in a variety of disorders such as epilepsy, Alzheimer's disease and obesity. For this purpose, novel N-substituted rhodanine derivatives (RhAs) w...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103096

    authors： Bayindir S,Caglayan C,Karaman M,Gülcin İ

    更新日期：2019-09-01 00:00:00

  • A novel synthesized sulfonamido-based gallic acid--LDQN-C: effects on chondrocytes growth and phenotype maintenance.

    abstract：:Chondrocyte based therapy is promising to treat symptomatic chondral and osteochondral lesions. Growth factors to accelerate the proliferation and retain the phenotype of chondrocytes in vitro are imperative. However, the high cost and rapid degradation of growth factors limited their further application. Therefore, i...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2014.09.005

    authors： Lu Z,Wei S,Wu H,Lin X,Lin C,Liu B,Zheng L,Zhao J

    更新日期：2014-12-01 00:00:00

  • Acetylenic fatty acids from Porcelia macrocarpa (Annonaceae) against trypomastigotes of Trypanosoma cruzi: Effect of octadec-9-ynoic acid in plasma membrane electric potential.

    abstract：:Porcelia macrocarpa (Warm.) R. E. Fries (Annonaceae) is an endemic plant in Brazil where its tasty pulp has been eaten fresh. The hexane extract from its flowers was subjected to chromatographic procedures to afford four acetylene derivatives identified as octadec-9-ynoic (stearolic acid - 1), (11E)-octadec-11-en-9-yn...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.03.025

    authors： Londero VS,da Costa-Silva TA,Gomes KS,Ferreira DD,Mesquita JT,Tempone AG,Young MCM,Jerz G,Lago JHG

    更新日期：2018-08-01 00:00:00

  • Compounds from the fruits of mangrove Sonneratia apetala: Isolation, molecular docking and antiaging effects using a Caenorhabditis elegans model.

    abstract：:The chemical investigation of the fruits of a mangrove Sonneratia apetala collected from the Beibu Gulf led to the isolation of four new compounds, sonneradons A-D (1-4), as well as 18 known compounds (5-22). The structures of the new compounds were elucidated based on extensive spectroscopic analysis, and the structu...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.103813

    authors： Yi X,Jiang S,Qin M,Liu K,Cao P,Chen S,Deng J,Gao C

    更新日期：2020-06-01 00:00:00

  • An NMR spectroscopy study of bendaline-albumin interactions.

    abstract：:The complete assignment of the 1H and 13C NMR spectra of bendaline (BNDL) was performed by mono-dimensional and homo- and hetero-correlated two-dimensional NMR experiments. The interaction between bendaline and albumin was also studied by the analysis of the motional parameters spin-lattice relaxation times, allowing ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/s0045-2068(03)00078-6

    authors： Delfini M,Bianchetti C,Di Cocco ME,Pescosolido N,Porcelli F,Rosa R,Rugo G

    更新日期：2003-10-01 00:00:00