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Antitumor Activity of Arylacetylshikonin Analogues

Kim, Seon-Hee    (College of Pharmacy, Chungnam National University   ); Song, Gyu-Yong    (College of Pharmacy, Chungnam National University   ); Jin, Guang-Zhu    (Department of Pharmacy, College of Medicine, University of Yanbian   ); Ahn, Byung-Zun    (college of Pharmacy, Chungnam National University  );
  • 초록

    Twenty one phenylacetylshikonin analogues were synthesized from various subsitituted phenyl acetic acids and their cytotoxicity values against A549, K562 and L1210 cell lines and antitumor action in mice bearing S-180 cells were measured. All of phenylacetylshikonin analogues expressed a potent cytotoxicity $(ED_{50}, 0.1-1.80{\mu}g/ml)$ against L1210 and K562 cells. L1210 cells were the most sensitive to shikonin analogues among these cells. Except 4-methosyphenylacetylshikonin $(0.098 {\mu}g/ml)$ , and a-acetoxyphenylacetylshikonin $(0.10 {\mu}g/ml)$ , all other shikonin derivatives sshowed higher $ED_{50}$ values than phenylacetylshikonin $(0.13{\mu}g/ml)$ , in L1210. In K562 cell, a-substitution of phenylacetylshikonin $(0.1{\mu}g/ml)$ , while other subsitutions increased it slightly; 4-methoxyphenylacetylshikonin $(0.033{\mu}g/ml)$ showed a exceptionally good cytotoxicity against K562 cell. 4-Halogenation tended to decrease the cytotoxic effect on L1210 cells, while it enhanced the effect on K562; 4-bromophenylacetyl $$[ED_{50};(L1210)=1.76{\mu}g/ml, ;ED_{50};(K 562)=0.32 {\mu}g/ml]$$ and 4-chlorophenylacetyl shikonin $$[ED_{50};(L1210)=1.64 {\mu}g/ml, ;ED_{50};(K562)=0.32 {\mu}g/ml]$$ . In contrast, A549 cells were much less sensitive to these shikonin analogues which showed $ED_{50}$ values of $1.5-1.35 {\mu}g/ml)$ .Most of phenylacetylshikonin derivatives showed good antitumor activity in mice bearing S-180 cells. a-A-cetoxyphenylacetylshikonin and 4-dimethylaminophenylacetylshikonin showed highest T/C value (192-195%), implying that introduction of a-acetyl or of 4-dimethylamino group enhanced the antitumor activity as shown for 4-dimethylaminophenylacetylshikonin (T/C, 192%). It might be due to improvement of water solubility by dimethylamino group in the molecule.


  • 주제어

    ARYLACETYLSHIKONIN .   SYNTHESIS .   CYTOTOXICITY .   ANTITUMOR ACTIVITY.  

  • 이 논문을 인용한 문헌 (1)

    1. Zheng, Xiang-Guo ; Jin, Guang-Zhu ; Song, Gyu-Yong ; Cho, Hoon ; Ahn, Byung-Zun 1998. "Haloacetylshikonin Derivatives : Synthesis and Evaluation of Antitumor Activity" 약학회지 = Yakhak hoeji, 42(2): 159~164     

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    2. 1994 "Synthesis of Dibenzoylmethanes as Intermediates for Flavone Synthesis by a Modified Baker-Venkataraman Rearrangement" Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea 17 (6): 434~437    
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  • Jin, Guang-Zhu (6)

  • Ahn, Byung-Zun (63)

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