当前位置： SCI文献检索 > EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY期刊下所有文献 > Structure-based discovery of selective BRPF1 bromodomain inhibitors.

Structure-based discovery of selective BRPF1 bromodomain inhibitors.

Abstract：

:Bromodomain and plant homeodomain (PHD) finger containing protein 1 (BRPF1) is a member of subfamily IV of the human bromodomains. Experimental evidence suggests that BRPF1 is involved in leukemia. In a previous high-throughput docking campaign we identified several chemotypes targeting the BRPF1 bromodomain. Here, pharmacophore searches using the binding modes of two of these chemotypes resulted in two new series of ligands of the BRPF1 bromodomain. The 2,3-dioxo-quinoxaline 21 exhibits a 2-μM affinity for the BRPF1 bromodomain in two different competition binding assays, and more than 100-fold selectivity for BRPF1 against other members of subfamily IV and representatives of other subfamilies. Cellular activity is confirmed by a viability assay in a leukemia cell line. Isothermal titration calorimetry measurements reveal enthalpy-driven binding for compounds 21, 26 (KD = 3 μM), and the 2,4-dimethyl-oxazole derivative 42 (KD = 10 μM). Multiple molecular dynamics simulations and a dozen co-crystal structures at high resolution provide useful information for further optimization of affinity for the BRPF1 bromodomain.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Zhu J,Zhou C,Caflisch A

doi

10.1016/j.ejmech.2018.05.037

subject

Has Abstract

pub_date

2018-07-15 00:00:00

pages

337-352

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(18)30450-1

journal_volume

155

pub_type

杂志文章

相关文献

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY文献大全
  • Structure-based drug design: Synthesis and biological evaluation of quinazolin-4-amine derivatives as selective Aurora A kinase inhibitors.

    abstract：:Aurora kinases play critical roles in the regulation of the cell cycle and mitotic spindle assembly. Aurora A kinase, a member of the Aurora protein family, is frequently highly expressed in tumors, and selective Aurora A inhibition serves as a significant component of anticancer therapy. However, designing highly sel...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2018.08.053

    authors： Long L,Wang YH,Zhuo JX,Tu ZC,Wu R,Yan M,Liu Q,Lu G

    更新日期：2018-09-05 00:00:00

  • Activity profile relationships between structurally similar promiscuous compounds.

    abstract：:Compound promiscuity results from specific interactions of a small molecule with multiple biological targets and is an emerging concept in medicinal chemistry and drug discovery as it provides the basis for polypharmacology. Recent studies have assessed the degree of promiscuity among drugs and bioactive compounds. On...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2013.08.044

    authors： Hu Y,Bajorath J

    更新日期：2013-11-01 00:00:00

  • Structure-activity analysis of CJ-15,801 analogues that interact with Plasmodium falciparum pantothenate kinase and inhibit parasite proliferation.

    abstract：:Survival of the human malaria parasite Plasmodium falciparum is dependent on pantothenate (vitamin B5), a precursor of the fundamental enzyme cofactor coenzyme A. CJ-15,801, an enamide analogue of pantothenate isolated from the fungus Seimatosporium sp. CL28611, was previously shown to inhibit P. falciparum proliferat...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2017.08.050

    authors： Spry C,Sewell AL,Hering Y,Villa MVJ,Weber J,Hobson SJ,Harnor SJ,Gul S,Marquez R,Saliba KJ

    更新日期：2018-01-01 00:00:00

  • QSAR study of heparanase inhibitors activity using artificial neural networks and Levenberg-Marquardt algorithm.

    abstract：:A linear and non-linear quantitative structure-activity relationship (QSAR) study is presented for modeling and predicting heparanase inhibitors' activity. A data set that consisted of 92 derivatives of 2,3-dihydro-1,3-dioxo-1H-isoindole-5-carboxylic acid, furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acids is u...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2007.04.014

    authors： Jalali-Heravi M,Asadollahi-Baboli M,Shahbazikhah P

    更新日期：2008-03-01 00:00:00

  • Synthesis, binding assays, cytotoxic activity and docking studies of benzimidazole and benzothiophene derivatives with selective affinity for the CB2 cannabinoid receptor.

    abstract：:Herein we report the design, synthesis, bioinformatic and biological studies of benzimidazole and benzothiophene derivatives as new cannabinoid receptor ligands. To test the hypothesis that the lack of a hydrogen bond interaction between benzimidazole and benzothiophene derivatives with Lys192 reduces their affinity f...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.08.005

    authors： Romero-Parra J,Mella-Raipán J,Palmieri V,Allarà M,Torres MJ,Pessoa-Mahana H,Iturriaga-Vásquez P,Escobar R,Faúndez M,Di Marzo V,Pessoa-Mahana CD

    更新日期：2016-11-29 00:00:00

  • TNF-α and IL-6 inhibitors: Conjugates of N-substituted indole and aminophenylmorpholin-3-one as anti-inflammatory agents.

    abstract：:The conjugates obtained by the combination of indole and aminophenyl morpholinone were screened for TNF-α and IL-6 inhibition in microglial cells. Compound 4 was found to be the most potent anti-inflammatory agent as it reduced LPS induced level of inflammatory cytokines TNF-α and IL-6 by 71% and 53%, respectively. A ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2017.09.003

    authors： Singh P,Kaur S,Sharma A,Kaur G,Bhatti R

    更新日期：2017-11-10 00:00:00

  • Pure enantiomers of benzoylamino-tranylcypromine: LSD1 inhibition, gene modulation in human leukemia cells and effects on clonogenic potential of murine promyelocytic blasts.

    abstract：:The pure enantiomers of the N-(2-, 3-, and 4-(2-aminocyclopropyl)phenyl)benzamides hydrochlorides 11a-j were prepared and tested against LSD1 and MAO enzymes. The evaluation of the regioisomers 11a-j highlighted a net increase of the anti-LSD1 potency by shifting the benzamide moiety from ortho to meta and mainly to p...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.02.060

    authors： Valente S,Rodriguez V,Mercurio C,Vianello P,Saponara B,Cirilli R,Ciossani G,Labella D,Marrocco B,Monaldi D,Ruoppolo G,Tilset M,Botrugno OA,Dessanti P,Minucci S,Mattevi A,Varasi M,Mai A

    更新日期：2015-04-13 00:00:00

  • Design, synthesis and pharmacological evaluation of N-benzyl-piperidinyl-aryl-acylhydrazone derivatives as donepezil hybrids: Discovery of novel multi-target anti-alzheimer prototype drug candidates.

    abstract：:A new series of sixteen multifunctional N-benzyl-piperidine-aryl-acylhydrazones hybrid derivatives was synthesized and evaluated for multi-target activities related to Alzheimer's disease (AD). The molecular hybridization approach was based on the combination, in a single molecule, of the pharmacophoric N-benzyl-piper...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2018.01.066

    authors： Dias Viegas FP,de Freitas Silva M,Divino da Rocha M,Castelli MR,Riquiel MM,Machado RP,Vaz SM,Simões de Lima LM,Mancini KC,Marques de Oliveira PC,Morais ÉP,Gontijo VS,da Silva FMR,D'Alincourt da Fonseca Peçanha D,Castro NG,N

    更新日期：2018-03-10 00:00:00

  • Structure-based design, synthesis and biological evaluation of novel anthra[1,2-d]imidazole-6,11-dione homologues as potential antitumor agents.

    abstract：:By using fragment-based design strategies, a series of 2-thio-substituted anthra[1,2-d]imidazole-6,11-diones were synthesized and evaluated for hTERT repressing activities, cell proliferations, and NCI 60-cell panel assay. Compounds 2, 3, 4, 11, 15 and 35 were selected by the NCI and 3, 4, 11 and 15 represent the GI₅₀...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2013.06.058

    authors： Chen TC,Yu DS,Huang KF,Fu YC,Lee CC,Chen CL,Huang FC,Hsieh HH,Lin JJ,Huang HS

    更新日期：2013-11-01 00:00:00

  • Discovery of novel, high potent, ABC type PTP1B inhibitors with TCPTP selectivity and cellular activity.

    abstract：:Protein tyrosine phosphatase 1B (PTP1B) as a key negative regulator of both insulin and leptin receptor pathways has been an attractive therapeutic target for the treatment of type 2 diabetes mellitus (T2DM) and obesity. With the goal of enhancing potency and selectivity of the PTP1B inhibitors, a series of methyl sal...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.04.014

    authors： Liu P,Du Y,Song L,Shen J,Li Q

    更新日期：2016-08-08 00:00:00

  • Organoiodine (III)-mediated synthesis of 3-aryl/heteroaryl-5,7-dimethyl-1,2,4-triazolo[4,3-c]pyrimidines as antibacterial agents.

    abstract：:Synthesis of 12 new 3-aryl/heteroaryl-5,7-dimethyl-1,2,4-triazolo[4,3-c]pyrimidines (3a-l) has been accomplished by the oxidation of pyrimidinylhydrazones (2a-l) of various aryl/heteroaryl aldehydes using 1.1equiv. of iodobenzene diacetate (IBD) in dichloromethane. All the compounds 3a-l tested in vitro for their anti...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2008.06.004

    authors： Kumar R,Nair RR,Dhiman SS,Sharma J,Prakash O

    更新日期：2009-05-01 00:00:00

  • Design, synthesis and structure-activity relationships of 4-phenyl-1H-1,2,3-triazole phenylalanine derivatives as novel HIV-1 capsid inhibitors with promising antiviral activities.

    abstract：:HIV-1 CA is involved in different stages of the viral replication cycle, performing essential roles in both early (uncoating, reverse transcription, nuclear import, integration) and late events (assembly). Recent efforts have demonstrated HIV-1 CA protein as a prospective therapeutic target for the development of new ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2020.112085

    authors： Sun L,Huang T,Dick A,Meuser ME,Zalloum WA,Chen CH,Ding X,Gao P,Cocklin S,Lee KH,Zhan P,Liu X

    更新日期：2020-03-15 00:00:00

  • Benzofuran-isatin hybrids and their in vitro anti-mycobacterial activities against multi-drug resistant Mycobacterium tuberculosis.

    abstract：:A series of benzofuran-isatin hybrids 6a-n and 7a-g linked by alkyl linkers were designed and synthesized. Among them, hybrids 6a-l and 7a-g were assessed for their in vitro anti-mycobacterial activities against two multi-drug resistant Mycobacterium tuberculosis (MDR-MTB) strains and the cytotoxicity towards CHO cell...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2019.111678

    authors： Gao F,Ye L,Wang Y,Kong F,Zhao S,Xiao J,Huang G

    更新日期：2019-12-01 00:00:00

  • Discovery of a new selective inhibitor of A Disintegrin And Metalloprotease 10 (ADAM-10) able to reduce the shedding of NKG2D ligands in Hodgkin's lymphoma cell models.

    abstract：:Hodgkin's lymphoma (HL) is the most common malignant lymphoma in young adults in the western world. This disease is characterized by an overexpression of ADAM-10 with increased release of NKG2D ligands, involved in an impaired immune response against tumor cells. We designed and synthesized two new ADAM-10 selective i...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.01.053

    authors： Camodeca C,Nuti E,Tepshi L,Boero S,Tuccinardi T,Stura EA,Poggi A,Zocchi MR,Rossello A

    更新日期：2016-03-23 00:00:00

  • 3,8-diazabicyclo--[3.2.1]-octane derivatives as analogues of ambasilide, a Class III antiarrhythmic agent.

    abstract：:Ambasilide, a representative of Class III antiarrhythmics, was reported to prolong the cardiac action potential duration in the dog, with little or no effect on Ca and Na currents. We synthesised a series of ambasilide analogues, having the 3,8-diazabicyclo-[3.2.1]-octane moiety instead of the 3,7-diazabicyclo-[3.3.1]...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0223-5234(01)01246-6

    authors： Villa S,Barlocco D,Cignarella G,Papp GJ,Baláti B,Takács J,Varró A,Borosy A,Keserû K,Mátyus P

    更新日期：2001-06-01 00:00:00

  • Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases.

    abstract：:The oxidation of bioorganic materials by air and, particularly, the oxidative stress involved in the cell loss and other pathologies associated with neurodegenerative diseases (NDs) are of enormous social and economic importance. NDs generally involve free radical reactions, beginning with the formation of an initiati...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2017.03.061

    authors： Losada-Barreiro S,Bravo-Díaz C

    更新日期：2017-06-16 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

  • Design, synthesis and preliminary bioactivity evaluations of 8-hydroxyquinoline derivatives as matrix metalloproteinase (MMP) inhibitors.

    abstract：:Matrix metalloproteinases (MMPs) play important roles in many diseases including cancer. With moderate metal-binding affinity, 8-hydroxyquinoline has gained much interest in current drug design and development. Specially, it has been reported that 8-hydroxyquinoline derivatives serve as MMP-2 inhibitors with micromola...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2019.111563

    authors： Chen C,Yang X,Fang H,Hou X

    更新日期：2019-11-01 00:00:00

  • Steroidal N-Sulfonylimidates: Synthesis and biological evaluation in breast cancer cells.

    abstract：:Unique derivatives of androstene and estrane series containing N-sulfonylimidate pendants were prepared from 17α-ethynyl steroids via Cu-catalyzed azide-alkyne cycloaddition to tosyl azide in the presence of alcohols. The synthesized compounds were screened for cytotoxicity against human breast cancer cell lines and E...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2019.06.048

    authors： Volkova YA,Kozlov AS,Kolokolova MK,Uvarov DY,Gorbatov SA,Andreeva OE,Scherbakov AM,Zavarzin IV

    更新日期：2019-10-01 00:00:00

  • Recent developments of coumarin-containing derivatives and their anti-tubercular activity.

    abstract：:Tuberculosis (TB) is a lift-threatening chronic deadliest infectious disease caused predominantly by Mycobacterium tuberculosis (MTB) which affects primarily the lungs (pulmonary TB) apart from other vital organs. The emergence of drug-resistant TB (DR-TB), multidrug-resistant TB (MDR-TB), extensively drug-resistant T...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2017.05.004

    authors： Hu YQ,Xu Z,Zhang S,Wu X,Ding JW,Lv ZS,Feng LS

    更新日期：2017-08-18 00:00:00

  • Medicinal plants used as anthelmintics: Ethnomedical, pharmacological, and phytochemical studies.

    abstract：:Intestinal parasites delay mental and physical development in children. Infection with these parasites can result in complications during pregnancy and alter the health of newborns, which has long-term effects on educational attainment and economic productivity. The appearance of resistance against classical drug trea...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2017.02.005

    authors： Romero-Benavides JC,Ruano AL,Silva-Rivas R,Castillo-Veintimilla P,Vivanco-Jaramillo S,Bailon-Moscoso N

    更新日期：2017-03-31 00:00:00

  • Platinum, palladium, gold and ruthenium complexes as anticancer agents: Current clinical uses, cytotoxicity studies and future perspectives.

    abstract：:Metallodrugs offer potential for unique mechanism of drug action based on the choice of the metal, its oxidation state, the types and number of coordinated ligands and the coordination geometry. This review illustrates notable recent progress in the field of medicinal bioinorganic chemistry as many new approaches to t...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2017.04.007

    authors： Lazarević T,Rilak A,Bugarčić ŽD

    更新日期：2017-12-15 00:00:00

  • Synthesis, antibacterial evaluation and QSAR studies of 7-[4-(5-aryl-1,3,4-oxadiazole-2-yl)piperazinyl] quinolone derivatives.

    abstract：:A series of 7-[4-(5-aryl-1,3,4-oxadiazole-2-yl)piperazinyl] quinolones (I-XXI) were synthesized using an appropriate synthetic route and characterized by elemental and spectral analysis. The antibacterial activities of all the synthesized compounds were evaluated against identifiable bacterial strains. Compounds III, ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2011.04.035

    authors： Kumar R,Kumar A,Jain S,Kaushik D

    更新日期：2011-09-01 00:00:00

  • Structure-activity relationships (SAR) of triazine derivatives: Promising antimicrobial agents.

    abstract：:The emergence of drug resistance has created unmet medical need for the development of new classes of antibiotics. Innovation of new antibacterial agents with new mode of action remains a high priority universally. Triazines are six-membered, nitrogen-containing heterocyclic scaffold with a wide range of pharmaceutica...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2019.111804

    authors： Liu H,Long S,Rakesh KP,Zha GF

    更新日期：2020-01-01 00:00:00

  • Synthesis and study of cytotoxic activity of 1,2,4-trioxane- and egonol-derived hybrid molecules against Plasmodium falciparum and multidrug-resistant human leukemia cells.

    abstract：:Malaria and cancer cause the death of millions of people every year. To combat these two diseases, it is important that new pharmaceutically active compounds have the ability to overcome multidrug resistance in cancer and Plasmodium falciparum strains. In search of effective anti-cancer and anti-malaria hybrids that p...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2014.01.043

    authors： Reiter C,Capcı Karagöz A,Fröhlich T,Klein V,Zeino M,Viertel K,Held J,Mordmüller B,Emirdağ Öztürk S,Anıl H,Efferth T,Tsogoeva SB

    更新日期：2014-03-21 00:00:00

  • The design of 8-hydroxyquinoline tetracyclic lactams as HIV-1 integrase strand transfer inhibitors.

    abstract：:A novel series of HIV-1 integrase strand transfer inhibitors were designed using the venerable two-metal binding pharmacophore model and incorporating structural elements from two different literature scaffolds. This manuscript describes a number of 8-hydroxyquinoline tetracyclic lactams with exceptional antiviral act...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.03.038

    authors： Velthuisen EJ,Johns BA,Temelkoff DP,Brown KW,Danehower SC

    更新日期：2016-07-19 00:00:00

  • Synthesis, characterization, evaluation and molecular dynamics studies of 5, 6-diphenyl-1,2,4-triazin-3(2H)-one derivatives bearing 5-substituted 1,3,4-oxadiazole as potential anti-inflammatory and analgesic agents.

    abstract：:A series of triazin-3(2H)-one derivatives bearing 1,3,4-oxadiazole (4a-4o) were synthesized, characterized and evaluated for anti-inflammatory and analgesic activities. Preliminary in vitro anti-inflammatory activity was assessed using an albumin denaturation assay. The promising compounds were further evaluated in ac...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.06.020

    authors： Banerjee AG,Das N,Shengule SA,Srivastava RS,Shrivastava SK

    更新日期：2015-08-28 00:00:00

  • Covalent and noncovalent constraints yield a figure eight-like conformation of a peptide inhibiting the menin-MLL interaction.

    abstract：:The interaction between menin and mixed lineage leukemia (MLL) was identified as an interesting target for treating some cancers including acute leukemia. On the basis of the known crystal structure of the MBM1-menin complex (MBM - menin binding motif), several cyclic peptides were designed. Elaboration of the effecti...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2020.112748

    authors： Fortuna P,Linhares BM,Purohit T,Pollock J,Cierpicki T,Grembecka J,Berlicki Ł

    更新日期：2020-12-01 00:00:00

  • Design, synthesis and bioevaluation of novel 6-(4-Hydroxypiperidino)naphthalen-2-ol-based potential Selective Estrogen Receptor Modulators for breast cancer.

    abstract：:In a study directed towards development of novel Selective Estrogen Receptor Modulators (SERMs), 1-(4-(2-(dialkylamino)ethoxy)benzyl)-6-(4-hydroxypiperidin-1-yl)-2-naphthol and corresponding aryl methyl ethers were synthesized and bioevaluated against the estrogen-responsive human MCF-7 breast cancer cell line. The ph...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2014.12.037

    authors： Jha A,Yadav Y,Naidu AB,Rao VK,Kumar A,Parmar VS,MacDonald WJ,Too CK,Balzarini J,Barden CJ,Cameron TS

    更新日期：2015-03-06 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