Synthesis and biological activities of phenylahistin derivatives

被引:65
作者
Kanoh, K [1 ]
Kohno, S [1 ]
Katada, J [1 ]
Takahashi, J [1 ]
Uno, I [1 ]
Hayashi, Y [1 ]
机构
[1] Nippon Steel Corp Ltd, Life Sci Res Ctr, Adv Technol Res Labs, Kawasaki, Kanagawa 2110035, Japan
关键词
amino acids and derivatives; antitumor compounds; X-ray crystal structure; natural products;
D O I
10.1016/S0968-0896(99)00059-0
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
X-ray crystallographic analysis was performed and several phenylahistin derivatives were synthesized to elucidate the structural components necessary for the anti-microtubule activity of phenylahistin. We primarily focused on the unique isoprenylated dehydrohistidine structure. Our results showed that a uniplanar pseudo-three-ring structure formed by the hydrogen bonding of diketopiperazine and imidazole rings is important for the anti-microtubule activity of phenylahistin. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1451 / 1457
页数:7
相关论文
共 11 条
[1]   A NEW RAPID AND SIMPLE NONRADIOACTIVE ASSAY TO MONITOR AND DETERMINE THE PROLIFERATION OF LYMPHOCYTES - AN ALTERNATIVE TO [H-3] THYMIDINE INCORPORATION ASSAY [J].
AHMED, SA ;
GOGAL, RM ;
WALSH, JE .
JOURNAL OF IMMUNOLOGICAL METHODS, 1994, 170 (02) :211-224
[2]  
BEURSKENS PT, 1991, DIRDIF94 PROGRAM SYS
[3]   THE SYNTHESIS OF VIRIDAMINE, A PENICILLIUM-VIRIDICATUM MYCOTOXIN [J].
BOND, RF ;
BREDENKAMP, MW ;
HOLZAPFEL, CW .
SYNTHETIC COMMUNICATIONS, 1989, 19 (13-14) :2551-2566
[4]  
FAN HF, 1991, STRUCTURE ANAL PROGR
[5]   KINETIC-ANALYSIS OF MICROTUBULE SELF-ASSEMBLY INVITRO [J].
JOHNSON, KA ;
BORISY, GG .
JOURNAL OF MOLECULAR BIOLOGY, 1977, 117 (01) :1-31
[6]   (-)-Phenylahistin arrests cells in mitosis by inhibiting tubulin polymerization [J].
Kanoh, K ;
Kohno, S ;
Katada, J ;
Takahashi, J ;
Uno, I .
JOURNAL OF ANTIBIOTICS, 1999, 52 (02) :134-141
[7]   (-)-phenylahistin: A new mammalian cell cycle inhibitor produced by Aspergillus ustus [J].
Kanoh, K ;
Kohno, S ;
Asari, T ;
Harada, T ;
Katada, J ;
Muramatsu, M ;
Kawashima, H ;
Sekiya, H ;
Uno, I .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (22) :2847-2852
[8]  
KANOH K, IN PRESS BIOSCI BIOT
[9]   AURANTIAMINE, A DIKETOPIPERAZINE FROM 2 VARIETIES OF PENICILLIUM-AURANTIOGRISEUM [J].
LARSEN, TO ;
FRISVAD, JC ;
JENSEN, SR .
PHYTOCHEMISTRY, 1992, 31 (05) :1613-1615
[10]   ORIGIN OF THE RING-RING INTERACTION IN CYCLIC DIPEPTIDES INCORPORATING AN AROMATIC AMINO-ACID [J].
LIWO, A ;
CIARKOWSKI, J .
TETRAHEDRON LETTERS, 1985, 26 (15) :1873-1876