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Selective Cell Targeting by High and Low Affinity Ligands on Cell Surface

Research Project

Project/Area Number 16K13104
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Chemical biology
Research InstitutionInstitute of Physical and Chemical Research

Principal Investigator

TANAKA Katsunori  国立研究開発法人理化学研究所, 田中生体機能合成化学研究室, 主任研究員 (00403098)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords生体分子 / 糖鎖 / 細胞 / 認識 / 有機化学
Outline of Final Research Achievements

In the field of molecular imaging, the target selectivity is one of the most important factors in determining the degree of imaging contrast. We developed an entirely unexplored idea that is based on a pre-targeting strategy by a) simultaneously recognizing two receptors using high- and low-affinity ligands and b) ligating them directly on the target cell surface. Glycan ligands with fluorescent label bound to the cell surface, even with mM binding affinity levels, can be tightly anchored by the pre-targeted high-affinity peptide ligand on the cell surface. The advantage of using low-affinity glycan ligands is that excess of the labeled glycans can be washed off from the cells. Through this approach, unspecific fluorescence background can be minimized. In this work, we demonstrated this strategy to differentiate various cancer cell lines by utilizing peptide and various different glycan structures.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • Research Products

    (56 results)

All 2018 2017 2016 Other

All Int'l Joint Research (1 results) Journal Article (13 results) (of which Int'l Joint Research: 10 results,  Peer Reviewed: 13 results,  Open Access: 13 results,  Acknowledgement Compliant: 4 results) Presentation (37 results) (of which Int'l Joint Research: 11 results,  Invited: 22 results) Remarks (5 results)

  • [Int'l Joint Research] Kazan Federal University(カザン連邦大学)(ロシア連邦)

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Convergent synthesis of a bisecting GlcNAc-containing N-glycan2018

    • Author(s)
      Manabe Yoshiyuki、Shomura Hiroki、Minamoto Naoya、Nagasaki Masahiro、Takakura Yohei、Tanaka Katsunori、Silipo Alba、Molinaro Antonio、Fukase Koichi
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 印刷中 Issue: 12 Pages: 1544-1551

    • DOI

      10.1002/asia.201800367

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Bis[N,N′-(2-indanolyl)]-1,5-diazacyclooctane as Unique Metal Ligand: Self-Assembly of Palladium Nanoparticles and Catalytic Reactivity on C?C Bond Formation2017

    • Author(s)
      Tanaka Katsunori、Fujiki Katsumasa
    • Journal Title

      Synthesis

      Volume: 50 Issue: 05 Pages: 1097-1104

    • DOI

      10.1055/s-0036-1590956

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] A One-Pot Three-Component Double-Click Method for Synthesis of [67Cu]-Labeled Biomolecular Radiotherapeutics2017

    • Author(s)
      K. Fujiki, S. Yano, T. Ito, Y. Kumagai, Y. Murakami, O. Kamigaito, H. Haba, K. Tanaka
    • Journal Title

      RIKEN Accel. Prog. Rep.

      Volume: 印刷中

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] What is medicinal chemistry? -Demystifying a rapidly evolving discipline!, MedChemComm opinion piece, “What is medicinal chemistry?”2017

    • Author(s)
      S. Y. L. Holbrook, S. Garneau-Tsodikova
    • Journal Title

      MeMed. Chem. Commun.

      Volume: 8 Issue: 9 Pages: 1739-1741

    • DOI

      10.1039/c7md90030a

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Effect of spermine-derived AGEs on oxidative stress and polyamine metabolism2017

    • Author(s)
      A. Tsutsui, A. R. Pradipta, S. Kitazume, N. Taniguchi, K. Tanaka
    • Journal Title

      Org. Biomol. Chem.

      Volume: 15 Issue: 32 Pages: 6720-6724

    • DOI

      10.1039/c7ob01346a

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] In-situ ligation of high- and low-affinity ligands to cell surface receptors enables highly selective recognition2017

    • Author(s)
      M. Taichi, S. Nomura, I. Nakase, R. Imamaki, Y. Kizuka, F. Ota, N. Dohmae, S. Kitazume, N. Taniguchi, K. Tanaka
    • Journal Title

      Adv. Sci.

      Volume: - Issue: 11 Pages: 1700147-1700147

    • DOI

      10.1002/advs.201700147

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Simple Gd3+-Neu5NAc complexation results in NMR chemical shift asymmetries of structurally equivalent complex-type N-glycan branches2017

    • Author(s)
      K. Usachev, Y. Yamaguchi, M. Takamatsu, N. Pavlova, V. Klochkov, A. Kurbangalieva, T. Murase, T. Shimoda, K. Tanaka
    • Journal Title

      Analyst

      Volume: 142 Issue: 16 Pages: 2897-2900

    • DOI

      10.1039/c7an00817a

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Cancer cell targeting driven by selective polyamine reactivity with glycine propargyl esters2017

    • Author(s)
      K. Vong, K. Tsubokura, Y. Nakao, T. Tanei, S. Noguchi, S. Kitazume, N. Taniguchi, K. Tanaka
    • Journal Title

      Chem. Commun.

      Volume: 53 Issue: 60 Pages: 8403-8406

    • DOI

      10.1039/c7cc01934c

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Reactivity of anti-HNK-1 antibodies to branched O-mannose glycans associated with demyelination2017

    • Author(s)
      K. Sakuda, Y. Kizuka, Y. Yamaguchi, K. Tanaka, K. Ogiwara, T. Segawa, Y. Hagiwara, I. Matsuo, H. Ogawa, N. Taniguchi, S. Kitazume
    • Journal Title

      Biochem. Biophys. Res. Commun.

      Volume: 487 Issue: 2 Pages: 450-456

    • DOI

      10.1016/j.bbrc.2017.04.085

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Highly reactive “RIKEN click” probe for glycoconjugation on lysines2017

    • Author(s)
      R. Sibgatullina, K. Fujiki, T. Murase, T. Yamamoto, T. Shimoda, A. Kurbangalieva, K. Tanaka
    • Journal Title

      Tetrahedron Lett.

      Volume: 印刷中 Issue: 20 Pages: 1929-1933

    • DOI

      10.1016/j.tetlet.2017.03.081

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] In vivo gold complex catalysis within live mice2017

    • Author(s)
      K. Tsubokura, K. K. H. Vong, A. R. Pradipta, A. Ogura, S. Urano, T. Tahara, S. Nozaki, H. Onoe, Y. Nakao, R. Sibgatullina, A. Kurbangalieva, Y. Watanabe, K. Tanaka
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 56 Issue: 13 Pages: 3579-3584

    • DOI

      10.1002/anie.201610273

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Sequential double “clicks” toward structurally well-defined heterogeneous N-glycoclusters: The importance of cluster heterogeneity on pattern recognition in vivo2017

    • Author(s)
      L. Latypova, R. Sibgatullina, A. Ogura, K. Fujiki, A. Khabibrakhmanova, T. Tahara, S. Nozaki, S. Urano, K, Tsubokura, H. Onoe, Y. Watanabe, A. Kurbangalieva, K. Tanaka
    • Journal Title

      Adv. Sci.

      Volume: 4 Issue: 2 Pages: 1600394-1600394

    • DOI

      10.1002/advs.201600394

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Chemically synthesized glycoconjugates on proteins: Effects of multivalency and glycoform in vivo2016

    • Author(s)
      K. Tanaka
    • Journal Title

      Org. Biomol. Chem.

      Volume: 14 Issue: 32 Pages: 7610-7621

    • DOI

      10.1039/c6ob00788k

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] ペプチドと糖鎖の協奏的な相互作用による選択的な細胞認識2018

    • Author(s)
      野村昌吾、田中克典
    • Organizer
      日本化学会第98春季年会、日本大学理工学部船橋キャンパス(千葉県船橋市)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 有機合成化学を起点とするものづくり戦略:趣意説明2018

    • Author(s)
      田中克典
    • Organizer
      日本化学会第98春季年会 特別企画 有機合成化学を起点とするものづくり戦略、日本大学理工学部船橋キャンパス(千葉県船橋市)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 糖鎖パターン認識DDSを基盤とする生体内合成化学治療2017

    • Author(s)
      田中克典
    • Organizer
      2017年度 生命科学系学会合同年次大会(ConBio2017)【ワークショップ】 新規分子骨格・ナノ材料で挑む細胞ターゲティングのためのネオ・レクチン分子創出戦略、神戸ポートアイランド(兵庫県神戸市)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 生体内合成化学治療2017

    • Author(s)
      田中克典
    • Organizer
      大塚合成シンポジウム、大塚製薬株式会社創薬化学研究所(徳島県徳島市)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Therapeutic in vivo synthetic chemistry2017

    • Author(s)
      Katsunori Tanaka
    • Organizer
      The 5th International Symposium on Transformative Bio-Molecules (ISTbM-5), Nagoya Univ.(Nagoya, Aichi)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Therapeutic in vivo synthetic chemistry2017

    • Author(s)
      Katsunori Tanaka
    • Organizer
      International Symposium, “Systems Glycobiology and Beyond” -Toward a bridge between fundamental research and applied science-, RIKEN Wako campus, Suzuki Umetaro Hall(Wako, Saitama)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Therapeutic in vivo synthetic chemistry2017

    • Author(s)
      Katsunori Tanaka
    • Organizer
      The 11th International Symposium on Integrated Synthesis (ISONIS11&ISMMS3), Awaji Yumebutai International Conference Center (Awaji Island, Hyogo)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 糖鎖を動物内での分子キャリアとする未来の有機合成化学:生体内合成化学治療2017

    • Author(s)
      田中克典
    • Organizer
      第11回多糖の未来フォーラム、大阪大学大学院理学研究科教育研究交流棟2階南部陽一郎ホール(大阪府豊中市)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Therapeutic in vivo synthetic chemistry2017

    • Author(s)
      Katsunori Tanaka
    • Organizer
      Departmental Talk in University of Strasbourg, University of Strasbourg(Strasbourg, France)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 生体を高度に見分ける糖鎖DDSと生体内での直接的な診断・治療2017

    • Author(s)
      田中克典
    • Organizer
      理研イブニングセミナー、理化学研究所東京連絡事務所(東京都千代田区)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 生体内合成化学治療2017

    • Author(s)
      田中克典
    • Organizer
      富士フイルム(株)有機合成化学研究所講演会、小田原富士フイルム先進研究所(神奈川県足柄上郡)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 細胞表面での糖鎖・ペプチド複合中分子合成によるがん種別選択的イメージング2017

    • Author(s)
      野村昌吾、伊藤昭博、吉田稔、田中克典
    • Organizer
      第36回日本糖質学会年会、旭川市民文化会館(北海道旭川市)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 糖鎖パターン認識による革新的DDSと生体内合成化学治療:検診、診断、そして治療へ2017

    • Author(s)
      田中克典
    • Organizer
      生化学工業株式会社講演会、生化学工業株式会社本社丸の内センタービルディング10F(東京都千代田区)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 生体分子複合化プローブとインビボプローブ合成2017

    • Author(s)
      田中克典
    • Organizer
      理化学研究所 Pioneering Project: Chemical Probe、理化学研究所和光事業所・統合支援施設大会議室(埼玉県和光市)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 糖鎖パターン認識による革新的DDSと生体内合成化学治療:検診、診断、そして治療へ2017

    • Author(s)
      田中克典
    • Organizer
      日油株式会社講演会、日油株式会社筑波研究センター 先端技術研究所(茨城県つくば市)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 糖鎖パターン認識による革新的DDSと生体内合成化学治療:検診、診断、そして治療へ2017

    • Author(s)
      田中克典
    • Organizer
      高分子同友会勉強会
    • Place of Presentation
      (社)高分子学会・高分子同友会事務局(東京都中央区)
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] ペプチド・糖鎖の共同相互作用を利用したがん細胞認識2017

    • Author(s)
      野村昌吾、田中克典
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス(神奈川県横浜市)
    • Related Report
      2016 Research-status Report
  • [Presentation] In vivo glycan-protein conjugation via metal catalysis2017

    • Author(s)
      Yixuan Lin, Kenward Vong, Koji Matsuoka, Katsunori Tanaka
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス(神奈川県横浜市)
    • Related Report
      2016 Research-status Report
  • [Presentation] In vivo pattern recognition by heterogeneous N-glycoclusters: Controlling excretion and tumor targetin2017

    • Author(s)
      Regina Sibgatullina, Liliya Latypova, Katsumasa Fujiki, Akihiro Ogura, Sayaka Urano, Tsuyoshi Tahara, Satoshi Nozaki, Yasuyoshi Watanabe, Almira Kurbangalieva, Katsunori Tanaka
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス(神奈川県横浜市)
    • Related Report
      2016 Research-status Report
  • [Presentation] Development of organ selective catalytic reaction by utilizing glycocluster2016

    • Author(s)
      Kazuki Tsubokura, Kenward Vong, Yoichi Nakao, Katsunori Tanaka
    • Organizer
      Summer School 2016, RIKEN
    • Place of Presentation
      International Congress Center(Tsukuba, Ibaraki)
    • Year and Date
      2016-09-09
    • Related Report
      2016 Research-status Report
  • [Presentation] 糖鎖クラスターを触媒キャリアとした生体内触媒反応2016

    • Author(s)
      坪倉一輝、Kenward Vong, 中尾洋一, 田中克典
    • Organizer
      第35回日本糖質学会年会
    • Place of Presentation
      高知文化プラザかるぽーと(高知県高知市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Research-status Report
  • [Presentation] 不均一糖鎖クラスターの生体内パターン認識による体外排出2016

    • Author(s)
      Regina Sibgatullina, Liliia Latypova, 藤木勝将、小椋章弘、田原強、野崎聡、浦野清香、尾上浩隆、渡辺恭良、Almira Kurbangalieva, 田中克典
    • Organizer
      第35回日本糖質学会年会
    • Place of Presentation
      高知文化プラザかるぽーと(高知県高知市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Research-status Report
  • [Presentation] 糖鎖クラスターを用いた生体内金属触媒反応の開発2016

    • Author(s)
      坪倉一輝, 中尾洋一, 田中克典
    • Organizer
      第51回天然物化学談話会
    • Place of Presentation
      湯沢東映ホテル(新潟県南魚沼郡)
    • Year and Date
      2016-07-06
    • Related Report
      2016 Research-status Report
  • [Presentation] 生体内合成化学治療:糖鎖クラスタを利用した生体内触媒反応の開発2016

    • Author(s)
      坪倉一輝, Kenward Vong, 田中克典
    • Organizer
      分子システム研究第5回春季研究会
    • Place of Presentation
      かんぽの宿熱海(神奈川県熱海市)
    • Year and Date
      2016-05-13
    • Related Report
      2016 Research-status Report
  • [Presentation] 生体内糖鎖認識の基盤と次世代セラノティクス -生体内パターン認識を駆使した革新的糖鎖複合体の開発 -2016

    • Author(s)
      田中克典
    • Organizer
      第14回糖鎖科学コンソーシアムシンポジウム
    • Place of Presentation
      ソラシティコンフェレンスセンター(東京都文京区)
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Cell Surface Synthesis of Targeting Molecules2016

    • Author(s)
      Katsunori Tanaka
    • Organizer
      3rd RIKEN - KFU Workshop
    • Place of Presentation
      Kazan Federal University(Kazan, Russia)
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Homogeneous Glycoconjugates2016

    • Author(s)
      Katsunori Tanaka
    • Organizer
      3rd RIKEN - KFU Workshop
    • Place of Presentation
      Kazan Federal University(Kazan, Russia)
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Post Translational Mimicry of Arginine to Therapeutic Molecules2016

    • Author(s)
      Katsunori Tanaka
    • Organizer
      3rd RIKEN - KFU Workshop
    • Place of Presentation
      Kazan Federal University(Kazan, Russia)
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Pattern Recognition In Vivo: Theranostics Glycoconjugates2016

    • Author(s)
      Katsunori Tanaka
    • Organizer
      International Conference in Organic Synthesis 2016
    • Place of Presentation
      Majestic Hotel(Kuching, Sarawak, Malaysia)
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Pattern Recognition In Vivo: Theranostics Glycoconjugates2016

    • Author(s)
      Katsunori Tanaka
    • Organizer
      Third FB3 Meeting
    • Place of Presentation
      Tianjin University: Science Library(Tianjin, China)
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Theranostic Glycoconjugates2016

    • Author(s)
      Katsunori Tanaka
    • Organizer
      Glycoscience Japan-Netherlands Joint Seminar 2016
    • Place of Presentation
      Leiden University Medial Center(Leiden, Netherlands)
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Heterogeneous Glycan-Clustering Leads to Highly Selective Target Recognition2016

    • Author(s)
      Katsunori Tanaka
    • Organizer
      RIKEN-Max Planck Joint Research Center 5th Annual Symposium
    • Place of Presentation
      Tagungshotel der Max-Planck-Gesellschaft(Berlin, Germany)
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Cell surface synthesis of targeting molecules2016

    • Author(s)
      Shogo Nomura, Katsunori Tanaka
    • Organizer
      異分野交流の夕べ、理化学研究所主催
    • Place of Presentation
      理化学研究所(埼玉県和光市)
    • Related Report
      2016 Research-status Report
  • [Presentation] Heterogeneous glycoconjugates2016

    • Author(s)
      Regina Sibgatullina, Katsunori Tanaka
    • Organizer
      異分野交流の夕べ、理化学研究所主催
    • Place of Presentation
      理化学研究所(埼玉県和光市)
    • Related Report
      2016 Research-status Report
  • [Presentation] In vivo sugar supplying method2016

    • Author(s)
      Yixuan Lin, Katsunori Tanaka
    • Organizer
      3rd RIKEN - KFU Workshop
    • Place of Presentation
      Kazan Federal University(Kazan, Russia)
    • Related Report
      2016 Research-status Report
  • [Presentation] Cell surface synthesis of targeting molecules2016

    • Author(s)
      Shogo Nomura, Katsunori Tanaka
    • Organizer
      3rd RIKEN - KFU Workshop
    • Place of Presentation
      Kazan Federal University(Kazan, Russia)
    • Related Report
      2016 Research-status Report
  • [Presentation] Heterogeneous glycoconjugates2016

    • Author(s)
      Regina Sibgatullina, Katsunori Tanaka
    • Organizer
      3rd RIKEN - KFU Workshop
    • Place of Presentation
      Kazan Federal University(Kazan, Russia)
    • Related Report
      2016 Research-status Report
  • [Remarks] 理化学研究所 開拓研究本部 田中生体機能合成化学研究室ホームページ

    • URL

      http://www.riken.jp/research/labs/chief/biofunct_synth_chem/

    • Related Report
      2017 Annual Research Report
  • [Remarks] 理化学研究所 開拓研究本部 田中生体機能合成化学研究室ホームページ(研究室オリジナルホームページ)

    • URL

      http://www.riken.jp/nori-tanaka-lab/

    • Related Report
      2017 Annual Research Report
  • [Remarks] プレスリリース:細胞を高度に見分ける新合成技術 -細胞表面上の有機反応で高選択的な細胞認識を実現-

    • URL

      http://www.riken.jp/pr/press/2017/20170728_1/

    • Related Report
      2017 Annual Research Report
  • [Remarks] 糖鎖は不均一であることが重要 -糖鎖特有の分子認識機構をマウスで解明-

    • URL

      http://www.riken.jp/pr/press/2016/20161128_1/

    • Related Report
      2016 Research-status Report
  • [Remarks] 生体内部を高度に認識できる糖鎖複合体 -糖鎖を用いた創薬や診断分子の開発に大きな手がかり-

    • URL

      http://www.riken.jp/pr/press/2016/20160223_3/

    • Related Report
      2016 Research-status Report

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Published: 2016-04-21   Modified: 2022-07-19  

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