エンジイン




エンジイン基の構造





カリケアミシン


エンジイン（enediyne）類は、微生物が産生する天然物の一群で、1つの二重結合によって隔てられた2つの三重結合を含む9あるいは10員環が特徴である[1]。これらの化合物の多くは、バーグマン環化を起こすことができる。得られるジラジカルである1,4-デヒドロベンゼン誘導体はDNAの糖鎖から水素結合を引き抜き、その結果DNA鎖が切断される[2]。このDNAに対する高い反応性により、これらの物質は毒性を示すため、抗腫瘍剤として研究が行われている。天然エンジイン類のいくつかは、がんに対する臨床試験へと進んでおり[3][4]、日本においてネオカルジノスタチンが臨床で用いられている。


エンジインは3つの分類が存在する。



  • カリケアミシン/エスペラミシン

  • ジネミシン

  • 色素タンパク質

これらの化合物中のエンジイン基はしばしば「弾頭」と呼ばれる。



脚注




  1. ^ K. C. Nicolaou; A. L. Smith; E. W. Yue (1993). “Chemistry and biology of natural and designed enediynes”. Proc Natl Acad Sci U.S.A. 90 (13): 5881–5888. Bibcode 1993PNAS...90.5881N. doi:10.1073/pnas.90.13.5881. PMC 46830. PMID 8327459. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC46830/. 


  2. ^ S. Walker; R. Landovitz; W.D. Ding; G.A. Ellestad; D. Kahne (1992). “Cleavage behavior of calicheamicin gamma 1 and calicheamicin T”. Proc Natl Acad Sci U.S.A. 89 (10): 4608–12. Bibcode 1992PNAS...89.4608W. doi:10.1073/pnas.89.10.4608. PMC 49132. PMID 1584797. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC49132/. 


  3. ^ Designed Enediyne Antitumor Agents


  4. ^ Development of Photoswitchable Enediyne Antibiotics








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