☆ 4.8 Article

An Efficient Light-Driven P450 BM3 Biocatalyst

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

期刊

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

卷 135, 期 39, 页码 14484-14487

出版社

AMER CHEMICAL SOC

DOI: 10.1021/ja409337v

关键词

-

类别

Chemistry, Multidisciplinary

资金

National Institute of Health [GM095415]
Research Corporation for Science Advancement
National Science Foundation (MRI) [0923573]
Direct For Biological Sciences
Div Of Biological Infrastructure [0923573] Funding Source: National Science Foundation

向作者/读者索取更多资源

Protocol

Reagent

摘要

P450s are heme thiolate enzymes that catalyze the regio- and stereoselective functionalization of unactivated C-H bonds using molecular dioxygen and two electrons delivered; by the reductase. We have developed hybrid P450 BM3 heme domains containing a covalently attached Ru(II) photosensitizer in order to circumvent the dependency on the reductase and perform P450 reactions upon visible light irradiation. A highly active hybrid enzyme with improved stability and a modified Ru(II) photosensitizer is able to catalyze the light driven hydroxylation of lauric acid with total turnover numbers of 935 and initial reaction rate of 125 mol product/(mol enzyme/miri).

作者

我是这篇论文的作者

点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.8

评分不足

次要评分

新颖性

-

重要性

-

科学严谨性

-

评价这篇论文

推荐

Review Chemistry, Physical

An Overview of Cytochrome P450 Immobilization Strategies for Drug Metabolism Studies, Biosensing, and Biocatalytic Applications: Challenges and Opportunities

Donya Valikhani, Juan M. Bolivar, Joelle N. Pelletier

Summary: Cytochrome P450s are a large superfamily of heme proteins with important applications in drug metabolism studies and biocatalytic transformations. Immobilization of P450 enzymes on biosensing platforms and in biocatalytic reactions plays a key role in improving operational stability. Various methods and materials have been developed to address the challenges associated with the unique characteristics of P450s in different applications.

ACS CATALYSIS (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Artificial Fusions between P450 BM3 and an Alcohol Dehydrogenase for Efficient (+)-Nootkatone Production

Arsenij Kokorin, Vlada B. Urlacher

Summary: In this study, fusion of P450 BM3 from Bacillus megaterium and an alcohol dehydrogenase from Sphingomonas yanoikuyae improved the two-step oxidation of (+)-valencene and resulted in increased production of (+)-nootkatone.

CHEMBIOCHEM (2022)

添加到收藏夹

Review Biochemistry & Molecular Biology

A Promiscuous Bacterial P450: The Unparalleled Diversity of BM3 in Pharmaceutical Metabolism

Sian Thistlethwaite, Laura N. Jeffreys, Hazel M. Girvan, Kirsty J. McLean, Andrew W. Munro

Summary: BM3 is a catalytically self-sufficient flavocytochrome fusion protein that can be engineered to produce a variety of drug-like compounds. Through modification of key residues within the BM3 active site, its catalytic repertoire can be expanded to generate diverse metabolites.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Prediction of Monomeric and Dimeric Structures of CYP102A1 Using AlphaFold2 and AlphaFold Multimer and Assessment of Point Mutation Effect on the Efficiency of Intra- and Interprotein Electron Transfer

Yuri D. Ivanov, Amir Taldaev, Andrey V. Lisitsa, Elena A. Ponomarenko, Alexander I. Archakov

Summary: The study predicted the three-dimensional structures of CYP102A1/WT proteins and their mutant forms using AlphaFold programs. The structures of monomers in the homodimer were found to be consistent with experimental structures, while the predicted structures of isolated monomers were different. Significant differences were observed in the structure of monomers compared to homodimers for the mutant forms. Comparative analysis showed a correlation between the electron transfer rate constants and the distances between prosthetic groups.

MOLECULES (2022)

添加到收藏夹

Article Biotechnology & Applied Microbiology

Oleic acid based experimental evolution of Bacillus megaterium yielding an enhanced P450 BM3 variant

Thierry Vincent, Bruno Gaillet, Alain Garnier

Summary: In this study, experimental evolution was used to enhance the total specific product output of BM3, resulting in the creation of a new variant named DE. The DE variant showed increased conversion of the substrate 10-pNCA to its product p-nitrophenolate, with 1.23 and 1.76-fold improvements when using NADPH or NADH as cofactors compared to the wild type BM3.

BMC BIOTECHNOLOGY (2022)

添加到收藏夹

Article Biotechnology & Applied Microbiology

Efficient hydroxylation of flavonoids by using whole-cell P450 sca-2 biocatalyst in Escherichia coli

Baodong Hu, Xinrui Zhao, Jingwen Zhou, Jianghua Li, Jian Chen, Guocheng Du

Summary: This study reports the development of a bacterial P450 sca-2(mut) whole-cell biocatalyst with remarkable 3'-hydroxylation activity for efficient hydroxylation of flavonoids. Flavodoxin Fld and flavodoxin reductase Fpr from Escherichia coli were used to enhance the whole-cell activity of sca-2(mut). Through enzymatic engineering, the double mutant of sca-2(mut) (R88A/S96A) exhibited improved hydroxylation performance for flavonoids. The optimized whole-cell biocatalytic conditions further enhanced the whole-cell activity of sca-2(mut) (R88A/S96A). Eriodictyol, dihydroquercetin, luteolin, and 7,3',4'-trihydroxyisoflavone were successfully produced as functionalized derivatives of flavonoids using naringenin, dihydrokaempferol, apigenin, and daidzein as substrates, with conversion yields of 77%, 66%, 32%, and 75% respectively. The strategy employed in this study offers an effective method for the hydroxylation of other high value-added compounds.

FRONTIERS IN BIOENGINEERING AND BIOTECHNOLOGY (2023)

添加到收藏夹

Article Biotechnology & Applied Microbiology

Enzymatic synthesis of indigo derivatives by tuning P450 BM3 peroxygenases

Li Ma, Tianjian Sun, Yunjie Liu, Yue Zhao, Xiaohui Liu, Yuxuan Li, Xinwei Chen, Lin Cao, Qianqian Kang, Jiawei Guo, Lei Du, Wei Wang, Shengying Li

Summary: In this study, cytochrome P450 BM3 was engineered into peroxygenases through directed evolution. These modified enzymes were used to selectively oxidize indole derivatives to produce a variety of indigoid pigments with a reduced band gap. These indigoid photocatalysts show promise for the development of new organic electronic devices.

SYNTHETIC AND SYSTEMS BIOTECHNOLOGY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Efficient Red-Light-Driven Hydrogen Evolution with an Anthraquinone Organic Dye

Mei Ming, Huiqing Yuan, Shuang Yang, Zuting Wei, Qinqin Lei, Jingxiang Lei, Zhiji Han

Summary: This study reports the use of a simple anthraquinone organic dye in an artificial photosynthetic system that efficiently utilizes red light for hydrogen generation. The system, which contains no noble metal, exhibits high turnover number and quantum yield, and holds promise for the development of renewable fuels in the future.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Biochemistry & Molecular Biology

The FMN 140s Loop of Cytochrome P450 Reductase Controls Electron Transfer to Cytochrome P450

Freeborn Rwere, Sangchoul Im, Lucy Waskell

Summary: By altering the 140s FMN binding loop of CYPOR, the activity with cyt P450s can be affected, with the mutant activity primarily determined by its ability to reduce ferric cyt P450. The different behaviors of the mutants are mainly due to the altered structure and mobility of the loop.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2021)

添加到收藏夹

Review Biochemistry & Molecular Biology

Cold-Adapted Proteases: An Efficient and Energy-Saving Biocatalyst

Zhengfeng Yang, Zhendi Huang, Qian Wu, Xianghua Tang, Zunxi Huang

Summary: Cold-adapted proteases have advantages such as high catalytic efficiency at low temperature and low energy input, making them economically and ecologically valuable. However, their application potential has not been fully developed, which has hindered their promotion in the industry.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

An efficient and recyclable Pickering magnetic interface biocatalyst: application in biodiesel production

Xiaobo Liu, Yuhua Mao, Siyang Yu, Hao Zhang, Kecheng Hu, Lingyu Zhu, Jianbing Ji, Jianli Wang

Summary: The study prepared a Pickering magnetic interface biocatalyst that can stabilize emulsions and achieve transesterification effectively, showing high catalytic activity. PI catalysis exhibited more significant activity compared to PAC, and the recycled catalyst maintained significant activity.

GREEN CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Applied

Introduction of aromatic amino acids in electron transfer pathways yielded improved catalytic performance of cytochrome P450s

Shuaiqi Meng, Zhongyu Li, Yu Ji, Anna Joelle Ruff, Luo Liu, Mehdi D. Davari, Ulrich Schwaneberg

Summary: By introducing aromatic amino acids on the electron transfer pathways of P450 BM3, the catalytic performance was improved. The best variant P2H02 showed a 13.9-fold increase in catalytic efficiency compared to P450 BM3 WT. Molecular dynamics simulations and electron hopping pathways analysis revealed that aromatic amino acid substitutions could increase electron transfer rates and improve catalytic performance. In addition, the introduction of tyrosines positively affected catalytic efficiency.

CHINESE JOURNAL OF CATALYSIS (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Efficient solar light-driven hydrogen generation using an Sn3O4 nanoflake/graphene nanoheterostructure

Yogesh A. Sethi, Aniruddha K. Kulkarni, Anuradha A. Ambalkar, Rajendra P. Panmand, Milind Kulkarni, Suresh W. Gosavi, Bharat B. Kale

Summary: In this study, Sn3O4/graphene composites were prepared for photocatalytic hydrogen generation, showing significantly improved solar light absorption and photoinduced charge separation. The incorporation of graphene in Sn3O4 led to a high photocatalytic hydrogen production rate due to improved electron transport and short diffusion distance, suggesting a promising strategy for designing high-performance energy-conversion devices with graphene nanoheterostructures.

RSC ADVANCES (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Efficient biocatalytic C-H bond oxidation: an engineered heme-thiolate peroxygenase from a thermostable cytochrome P450

Alecia R. Gee, Isobella S. J. Stone, Tegan P. Stockdale, Tara L. Pukala, James J. De Voss, Stephen G. Bell

Summary: We have achieved efficient oxidation reactions on unactivated carbon-hydrogen bonds by modifying the enzyme structure.

CHEMICAL COMMUNICATIONS (2023)

添加到收藏夹

Article Materials Science, Multidisciplinary

Highly efficient visible-light-driven Cu2O@CdSe micromotors adsorbent

Xiao Chen, Xiaoyong Ding, Yilin Liu, Jing Li, Wenjuan Liu, Xiaolong Lu, Zhongwei Gu

Summary: Visible light-driven Cu2O@CdSe micromotors with excellent removal performance and effective motion regulation show promising applications in micro environmental remediation.

APPLIED MATERIALS TODAY (2021)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

Correlating the para-Substituent Effects on Ru(II)-Polypyridine Photophysical Properties and on the Corresponding Hybrid P450 BM3 Enzymes Photocatalytic Activity

Hadil Shalan, Alexander Colbert, Thanh Truc Nguyen, Mallory Kato, Lionel Cheruzel

INORGANIC CHEMISTRY (2017)

添加到收藏夹

Article Medicine, Research & Experimental

Biorelevant Dissolution Models for a Weak Base To Facilitate Formulation Development and Overcome Reduced Bioavailability Caused by Hypochlordyria or Achlorhydria

Dawen Kou, Sudharsan Dwaralmath, Yannick Fischer, Daniel Nguyen, Myeonghui Kim, Hiuwing Yiu, Preeti Patel, Tania Ng, Chen Mao, Matthew Durk, Leslie Chinn, Helen Winter, Larry Wigman, Peter Yehl

MOLECULAR PHARMACEUTICS (2017)

添加到收藏夹

Article Biochemistry & Molecular Biology

Keeping the spotlight on cytochrome P450

Hadil Shalan, Mallory Kato, Lionel Cheruzel

BIOCHIMICA ET BIOPHYSICA ACTA-PROTEINS AND PROTEOMICS (2018)

添加到收藏夹

Article Biochemistry & Molecular Biology

Cross-linked cytochrome P450 BM3 aggregates promoted by Ru(II)-diimine complexes bearing aldehyde groups

Minh Quan Do, Evelynn Henry, Mallory Kato, Lionel Cheruzel

JOURNAL OF INORGANIC BIOCHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Physical

Selective Light-Driven Chemoenzymatic Trifluoromethylation/Hydroxylation of Substituted Arenes

Victor Sosa, Marya Melkie, Carolina Sulca, Jennifer Li, Lawrence Tang, Jeffrey Li, Justin Faris, Bridget Foley, Tam Banh, Mallory Kato, Lionel E. Cheruzel

ACS CATALYSIS (2018)

添加到收藏夹

Article Biochemistry & Molecular Biology

Coupling efficiency in light-driven hybrid P450BM3 and CYP119 enzymes

Mallory Kato, Marya Melkie, Jeffrey Li, Bridget Foley, Hoang Truc Nguyen, Liridona Leti, Lionel Cheruzel

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS (2019)

添加到收藏夹

Article Multidisciplinary Sciences

Quantitative microscopy reveals dynamics and fate of clustered IRE1α

Vladislav Belyy, Ngoc-Han Tran, Peter Walter

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2020)

添加到收藏夹

Article Multidisciplinary Sciences

Ribosome-associated vesicles: A dynamic subcompartment of the endoplasmic reticulum in secretory cells

Stephen D. Carter, Cheri M. Hampton, Robert Langlois, Roberto Melero, Zachary J. Farino, Michael J. Calderon, Wen Li, Callen T. Wallace, Ngoc Han Tran, Robert A. Grassucci, Stephanie E. Siegmund, Joshua Pemberton, Travis J. Morgenstern, Leanna Eisenman, Jenny Aguilar, Nili L. Greenberg, Elana S. Levy, Edward Yi, William G. Mitchell, William J. Rice, Christoph Wigge, Jyotsna Pilli, Emily W. George, Despoina Aslanoglou, Maite Courel, Robin J. Freyberg, Jonathan A. Javitch, Zachary P. Wills, Estela Area-Gomez, Sruti Shiva, Francesca Bartolini, Allen Volchuk, Sandra A. Murray, Meir Aridor, Kenneth N. Fish, Peter Walter, Tamas Balla, Deborah Fass, Sharon G. Wolf, Simon C. Watkins, Jose Maria Carazo, Grant J. Jensen, Joachim Frank, Zachary Freyberg

SCIENCE ADVANCES (2020)

添加到收藏夹

Article Biochemistry & Molecular Biology

Promoting P450 BM3 heme domain dimerization with a tris(5-iodoacetamido-1,10-phenanthroline)Ru(II) complex

Mallory Kato, Bridget Foley, Julia Vu, Michael Huynh, Kathreena Lucero, Caroline Harmon, Lionel Cheruzel

BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY (2020)

添加到收藏夹

Review Biochemistry & Molecular Biology

Ru(II)-diimine complexes and cytochrome P450 working hand-in-hand

Celine Eidenschenk, Lionel Cheruzel

JOURNAL OF INORGANIC BIOCHEMISTRY (2020)

添加到收藏夹

Article Cell Biology

The WAVE complex associates with sites of saddle membrane curvature

Anne Pipathsouk, Rachel M. Brunetti, Jason P. Town, Brian R. Graziano, Artu Breuer, Patrina A. Pellett, Kyle Marchuk, Ngoc-Han T. Tran, Matthew F. Krummel, Dimitrios Stamou, Orion D. Weiner

Summary: The study reveals that the WAVE complex forms actin-independent rings at regions of saddle membrane curvature, suggesting its role in organizing sheet-like lamellipodia and other emergent cell behaviors beyond Arp2/3 complex activation. Moreover, the WAVE complex recruits IRSp53 to these sites but does not depend on it for its own localization.

JOURNAL OF CELL BIOLOGY (2021)

添加到收藏夹

Article Chemistry, Analytical

Characterization of Impurities in Therapeutic RNAs at the Single Nucleotide Level

Alexandre Goyon, Daniel Nguyen, Sara Boulanouar, Peter Yehl, Kelly Zhang

Summary: The study developed a workflow to investigate the degradation of gRNA at the single nucleotide level, identifying residues prone to degradation. Analysis of stressed gRNA samples revealed that desulfurization of phosphorothioate linkages was the major degradation observed.

ANALYTICAL CHEMISTRY (2022)

添加到收藏夹

Review Pharmacology & Pharmacy

Biotransformation research advances-2022 year in review

S. Cyrus Khojasteh, Upendra A. Argikar, Lionel Cheruzel, Sungjoon Cho, Rachel D. Crouch, Deepika Dhaware, Carley J. S. Heck, Kevin M. Johnson, Amit S. Kalgutkar, Lloyd King, Joyce Liu, Bin Ma, Hlaing Maw, Grover P. Miller, Herana Kamal Seneviratne, Ryan H. Takahashi, Shuai Wang, Cong Wei, Klarissa D. Jackson, Robin Mcdougall, Diane Ramsden, Sagar Agarwal, Saket Agarwal, Krishna Aluri, Michael Arciprete, Christopher Brown, Elena Castellanos-Rizaldos, Klaus Charisse, Saeho Chong, Joseph Cichocki, Kevin Fitzgerald, Varun Goel, Yongli Gu, Dale Guenther, Bahru Habtemariam, Vasant Jadhav, Maja Janas, Muthusamy Jayaraman, Jeffrey Kurz, Jing Li, Ju Liu, Xiumin Liu, Steven Liou, Chris Maclauchlin, Martin Maier, Muthiah Manoharan, Jayaprakash K. Nair, Gabriel Robbie, Karyn Schmidt, Peter Smith, Christopher Theile, Akshay Vaishnaw, Scott Waldron, Yuanxin Xu, Xuemei Zhang, Ivan Zlatev, Jing-Tao Wu, Julia M. Migliorati, Sunna Liu, Anna Liu, Anagha Gogate, Sreenidhi Nair, Raman Bahal, Theodore P. Rasmussen, Jose E. Manautou, Xiao-bo Zhong, Peter S. Dragovich, Sarah Wolfson, Reese Hitchings, Karina Peregrina, Ziv Cohen, Saad Khan, Tugba Yilmaz, Marcel Malena, Edgar Goluch, Leonard Augenlicht, Libusha Ray, Peter Spanogiannopoulos, Than S. Kyaw, Ben G. H. Guthrie, Patrick H. Bradley, Joyce V. Lee, Jonathan Melamed, Ysabella Noelle Amora Malig, Kathy N. Lam, Daryll Gempis, Moriah Sandy, Wesley Kidder, Erin L. Van Blarigan, Chloe E. Atreya, Alan Venook, Roy R. Gerona, Andrei Goga, Katherine S. Pollard, Peter J. Turnbaugh, Upendra P. Dahal, Brooke M. Rock, John Rodgers, Xiaomeng Shen, Zhe Wang, Jan L. Wahlstrom, Ravi Shankar P. Singh, Gregory S. Walker, Eugene P. Kadar, Loretta M. Cox, Heather Eng, Raman Sharma, Arthur J. Bergman, Lien Van Eyck, Frances Hackman, Sima Toussi, Amit S. Kalgutkar, R. Scott Obach, Yasuhiro Uno, Shiori Jikuya, Yutaro Noda, Norie Murayama, Hiroshi Yamazaki, Marie-Noelle Paludetto, Mika Kurkela, Helinae Kahma, Janne T. Backman, Mikko Niemi, Anne M. Filppula, Pritam Roy, David G. Dennis, Mark D. Eschbach, Shravanthi D. Anand, Fengyun Xu, Jonathan Maturano, Judith Hellman, David Sarlah, Aditi Das, Sumit Bansal, Mary F. Paine, Jashvant D. Unadkat, R. Scott Obach, Mario Oeeren, Peter J. Walton, James Suri, David J. Ponting, Peter A. Hunt, Matthew D. Segall, A. Le, K. J. Huang, L. R. Cirrincione, Jinghan Liu, Heather A. Carlson, Emily E. Scott, Hinata Ueda, Katsuya Narumi, Ayako Furugen, Yoshitaka Saito, Masaki Kobayashi, Nadia O. Bamfo, Jessica Bl Lu, Zeruesenay Desta, N. Milani, N. Qiu, S. Fowler, Slobodan P. Rendic, Rachel D. Crouch, F. Peter Guengerich, David Pearson, Yi Jin, Andrea Romeo, Bertrand-Luc Birlinger, Hilmar Schiller, Yan Ji, Mithat Gunduz, Daniela Baldoni, Markus Walles, Longbin Liu, Peter D. Johnson, Michael E. Prime, Vinod Khetarpal, Christopher J. Brown, Luca Anzillotti, Daniele Bertoglio, Xuemei Chen, Samuel Coe, Randall Davis, Anthony P. Dickie, Simone Esposito, Elise Gadouleau, Paul R. Giles, Catherine Greenaway, James Haber, Christer Halldin, Scott Haller, Sarah Hayes, Todd Herbst, Frank Herrmann, Manuela Hessmann, Ming Min Hsai, Yaser Khani, Adrian Kotey, Angelo Lembo, John E. Mangette, Gwendolyn A. Marriner, Richard W. Marston, Matthew R. Mills, Edith Monteagudo, Anton Forsberg-Moren, Sangram Nag, Laura Orsatti, Christine Sandiego, Sabine Schaertl, Joanne Sproston, Steven Staelens, Jack Tookey, Penelope A. Turner, Andrea Vecchi, Maria Veneziano, Ignacio Munoz-Sanjuan, Jonathan Bard, Celia Dominguez, Alexander Sokolsky, Sarah Winterton, Keith Kennedy, Katherine Drake, Kristine Stump, Lu Huo, Yvonne Lo, Min Ye, Maryanne Covington, Sharon Diamond, Yan-ou Yang, Sunkyu Kim, Swamy Yeleswaram, Liangxing Wu, Wenqing Yao

Summary: CBG is a phytocannabinoid with widespread medical applications and beneficial effects in the treatment of various diseases. Recent studies have identified the metabolic pathways of CBG and demonstrated its anti-inflammatory properties. These findings are important for understanding the pharmacological effects and clinical potential of CBG.

DRUG METABOLISM REVIEWS (2023)

添加到收藏夹

Article Biochemical Research Methods

Characterization of antisense oligonucleotide and guide ribonucleic acid diastereomers by hydrophilic interaction liquid chromatography coupled to mass spectrometry

Alexandre Goyon, Molly S. Blevins, Jose G. Napolitano, Daniel Nguyen, Meenakshi Goel, Brandon Scott, Jenny Wang, Stefan G. Koenig, Tao Chen, Kelly Zhang

Summary: Oligonucleotides have become an important therapeutic modality, but their characterization is challenging due to their unique chemical structure. This study investigates the stereochemistry of fully-modified and partially-modified oligonucleotides using HILIC and other techniques, and proposes a new strategy for characterizing oligonucleotide stereochemistry.

JOURNAL OF CHROMATOGRAPHY A (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Tryptophan scanning mutagenesis as a way to mimic the compound-bound state and probe the selectivity of allosteric inhibitors in cells

Isabelle R. Taylor, Victoria A. Assimon, Szu Yu Kuo, Silvia Rinaldi, Xiaokai Li, Zapporah T. Young, Giulia Morra, Keith Green, Daniel Nguyen, Hao Shao, Sylvie Garneau-Tsodikova, Giorgio Colombo, Jason E. Gestwicki

CHEMICAL SCIENCE (2020)

添加到收藏夹

暂无数据

© Peeref 2019-2024. All rights reserved.