Mitomycinoid alkaloids: mechanism of action, biosynthesis, total syntheses, and synthetic approaches.
Mitomycinoid alkaloids: mechanism of action, biosynthesis, total syntheses, and synthetic approaches.
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DOI：
10.1021/cr3001059
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发表时间：
2013-08-14
期刊：
影响因子：
62.1
通讯作者：
Williams, Robert M.
中科院分区：
文献类型：
--
作者：
Bass, Phillip D.;Gubler, Daniel A.;Judd, Ted C.;Williams, Robert M.
丝裂霉素（图1）是具有丰富历史的独特天然产物家族。1956年，日本Kwoya Hakko Kogyo Co.的Hata及其同事首次从土壤样本中发现的Streptomyces caespitosus中分离出丝裂霉素A和B。1− 3虽然丝裂霉素是由Kwoya Hakko Kogyo的研究人员分离出来的，但丝裂霉素的绝对结构是由美国Cyanamid公司的Webb和同事确定的。从那时起，这个天然产物家族的许多其他成员也被分离出来，包括1988年从桑达链霉菌中分离出的FR-900482和FR-66979（图1）。8，9归因于该天然产物家族的生物活性是其在小沟中形成链间和链内DNA交联的能力的表现，其特异性有利于5′-CG-3′步骤。10，11在这一发现的时候，还没有已知的天然产物作为DNA交联剂的例子。在这一初步发现之后，发现其他几种天然产物也与DNA形成交联。最近的研究表明，除了形成DNA交联外，这个化合物家族还能够与小沟结合核蛋白形成交联，例如高迁移率族I/Y（HMG I/Y，现在称为HMG A1）蛋白。15，16此外，当FR-900482衍生物与核小体一起孵育时，发现单烷基化而非交联是主要加合物。这一结果可能表明该天然产物家族在细胞染色质中的替代作用模式。
The mitomycins (Figure 1) are a unique family of natural products with a rich history. Hata and co-workers at Kwoya Hakko Kogyo Co. in Japan first isolated mitomycins A and B from Streptomyces caespitosus found in soil samples in 1956. 1− 3 Although the mitomycins were isolated by researchers at Kwoya Hakko Kogyo, the absolute structure of the mitomycins was determined by Webb and co-workers at the American Cyanamid Co. 4, 5 X-ray crystal structures of the mitomycins by Tulinsky also proved critical in determination of the structures of the mitomycins. 6, 7 Since that time a number of other members of this family of natural products have been isolated, including FR-900482 and FR-66979 from Streptomyces sandaensis in 1988 (Figure 1). 8, 9 The biological activity attributed to this family of natural products is a manifestation of their ability to form both interand intrastrand DNA cross-links in the minor groove with a specificity favoring 5′-CG-3′ steps. 10, 11 At the time of this discovery, no previous examples of natural products acting as DNA cross-linking agents were known. It was after this initial finding that several other natural products were found to also form cross-links with DNA. 12− 14 Recent studies have shown that in addition to formation of DNA cross-links, this family of compounds is also capable of forming cross-links with minorgroove-binding nuclear proteins, such as high-mobility group I/Y (HMG I/Y now named HMG A1) proteins. 15, 16 Additionally, it was shown that monoalkylation and not cross-linking was the major adduct found when an FR-900482 derivative was incubated with nucleosomes. This result could suggest alternate modes of action of this family of natural products in the context of cellular chromatin.
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影响因子：
1.8
作者：
Ahmed, A;Clayden, J;Rowley, M
通讯作者：
Rowley, M
DOI：
10.1039/p19800000097
发表时间：
1980-01-01
期刊：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
影响因子：
--
作者：
BAILEY, AS;SCOTT, PW;VANDREVALA, MH
通讯作者：
VANDREVALA, MH
DOI：
10.1073/pnas.93.24.13623
发表时间：
1996-11-26
影响因子：
11.1
作者：
Bailly, C;Payet, D;Waring, MJ
通讯作者：
Waring, MJ
影响因子：
3.6
作者：
AKIBA, M;KOSUGI, Y;TAKADA, T
通讯作者：
TAKADA, T
影响因子：
5.7
作者：
Adikesavan, Anbu Karani;Jaiswal, Anil K.
通讯作者：
Jaiswal, Anil K.