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Neocarzinostatin (NCS) is a macromolecular chromoprotein enediyne antitumor antibiotic secreted by Streptomyces macromomyceticus. It consists of two parts, a labile chromophore (the non-protein molecular entity shown at right) and a 113 amino acid protein to which the chromophore is tightly and non-covalently bound with high affinity (Kd ~ 10−10 M). The non-protein component is a very potent DNA-damaging agent; However it is extremely unstable and the role of the protein is to protect it and release it to the target DNA. Opening of the epoxide under reductive conditions present in cells creates favorable conditions for a Masamune-Bergman cyclization, leading to formation of benzyne, followed by DNA strand cleavage. Another important member of the chromoprotein group of natural products is

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rdf:type
rdfs:label
  • Zinostatin (de)
  • Zinostatina (it)
  • Neocarzinostatin (en)
  • ネオカルジノスタチン (ja)
rdfs:comment
  • La zinostatina (nota anche con il nome di neocarzinostatina) è un antibiotico,un alchene appartenente alla famiglia delle enediyne (ovvero composti con tripli legami per ogni lato di un doppio legame), dotato di attività antitumorale. La molecola è un polipeptide, più precisamente una apoproteina, consistente di due parti, una proteica del peso molecolare di 10.700, contenente 109 residui aminoacidici di 18 tipi differenti, e di un cromoforo, labile, di natura non proteica, con struttura biciclica, responsabile della attività biologica della sostanza. Nella molecola sono presenti due ponti disolfuro tra la cisteina. L'integrità della struttura, ivi compreso il collegamento trasversale dei ponti disolfuro, è essenziale per l'espletamento dell'attività biologica. (it)
  • ネオカルジノスタチン (neocarzinostatin) は、Streptomyces macromomyceticusによって分泌される高分子エンジイン抗生物質である。抗腫瘍活性を示す。ネオカルチノスタチンとも呼ばれる。 ネオカルジノスタチンは不安定な発色団（二環性ジエンジイン構造）と113アミノ酸からなるアポタンパク質の2つの部分からなり、アポタンパク質と発色団は非共有結合的にしっかりと高い親和性 (Kd ~ 10-10 M) で結合している。発色団は非常に強力なDNA損傷剤である。発色団は非常に不安定であり、アポタンパク質は発色団を保護し、標的とするDNAへ放出する役割を果たしている。細胞中に存在する還元的条件下でのエポキシドの開環によって、バーグマン環化のための条件が整えられ、その後ジラジカル中間体の産生とDNA二重鎖の切断が起こる。その他のネオカルジノスタチン類抗生物質にはマクロモミシンや、、マズロペプチンがある。 抗腫瘍薬としては最も強力な化合物の一つである。 (ja)
  • Zinostatin (auch: Neocarzinostatin) ist ein Arzneistoff aus der Gruppe der Endiin-Antibiotika mit antineoplastischer Wirkung. Verantwortlich für die Antitumor-Wirkung ist ein chromophorer Teil, der nicht-kovalent an ein aus 113 Aminosäuren bestehendes Apoprotein gebunden ist. Das Chromophor ist ohne die Bindung an das Peptid chemisch instabil. Das Peptid besteht aus einer einzigen Kette. Zinostatin wird aus Kulturen von Streptomyces carcinostaticus var. F-41 gewonnen. Das Neocarzinostatin-Chromophor verursacht an der DNA Strangbrüche, bevorzugt an der Desoxyribose des Thymins. (de)
  • Neocarzinostatin (NCS) is a macromolecular chromoprotein enediyne antitumor antibiotic secreted by Streptomyces macromomyceticus. It consists of two parts, a labile chromophore (the non-protein molecular entity shown at right) and a 113 amino acid protein to which the chromophore is tightly and non-covalently bound with high affinity (Kd ~ 10−10 M). The non-protein component is a very potent DNA-damaging agent; However it is extremely unstable and the role of the protein is to protect it and release it to the target DNA. Opening of the epoxide under reductive conditions present in cells creates favorable conditions for a Masamune-Bergman cyclization, leading to formation of benzyne, followed by DNA strand cleavage. Another important member of the chromoprotein group of natural products is (en)
foaf:name
  • Neocarzinostatin chromophore (en)
name
  • Neocarzinostatin chromophore (en)
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  • http://commons.wikimedia.org/wiki/Special:FilePath/Neocarzinostatin.png
  • http://commons.wikimedia.org/wiki/Special:FilePath/Neocarzinostatin_3D_spacefill.png
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