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Literature DB >> 12952479

DNA alkylation properties of yatakemycin.

Jay P Parrish¹, David B Kastrinsky, Scott E Wolkenberg, Yasuhiro Igarashi, Dale L Boger.

Abstract

Yatakemycin represents the newest and now most potent member of a class of naturally occurring antitumor compounds that includes CC-1065 and the duocarmycins, which derive their biological properties from a characteristic DNA alkylation reaction. Herein, the first description of the yatakemycin DNA alkylation properties is detailed, constituting the first such study of a naturally occurring "sandwiched" member of this class. Thus, the event, sequence selectivity, relative rate and efficiency, and reversibility of the DNA alkylation reaction of yatakemycin are described.

Entities: Chemical

Mesh：

Substances：

Year: 2003 PMID： 12952479 DOI： 10.1021/ja035984h

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

28 in total

1. Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]oxazolo[2,3-e]indol-4-one-6-carboxylate (COI) alkylation subunit.

Authors: Kristopher E Boyle; Karen S MacMillan; David A Ellis; James P Lajiness; William M Robertson; Dale L Boger
Journal: Bioorg Med Chem Lett Date: 2010-02-02 Impact factor: 2.823

2. Systematic exploration of the structural features of yatakemycin impacting DNA alkylation and biological activity.

Authors: Mark S Tichenor; Karen S MacMillan; John D Trzupek; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal: J Am Chem Soc Date: 2007-08-11 Impact factor: 15.419

3. A five-membered lactone prodrug of CBI-based analogs of the duocarmycins.

Authors: Mika Uematsu; Daniel M Brody; Dale L Boger
Journal: Tetrahedron Lett Date: 2015-06-03 Impact factor: 2.415

4. Synthesis and evaluation of a series of C5'-substituted duocarmycin SA analogs.

Authors: William M Robertson; David B Kastrinsky; Inkyu Hwang; Dale L Boger
Journal: Bioorg Med Chem Lett Date: 2010-03-25 Impact factor: 2.823

5. Asymmetric total synthesis of (+)- and ent-(-)-yatakemycin and duocarmycin SA: evaluation of yatakemycin key partial structures and its unnatural enantiomer.

Authors: Mark S Tichenor; John D Trzupek; David B Kastrinsky; Futoshi Shiga; Inkyu Hwang; Dale L Boger
Journal: J Am Chem Soc Date: 2006-12-13 Impact factor: 15.419

Review 10. Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065.

Authors: Karen S MacMillan; Dale L Boger
Journal: J Med Chem Date: 2009-10-08 Impact factor: 7.446

DNA alkylation properties of yatakemycin.

1. Synthesis and evaluation of duocarmycin SA analogs incorporating the methyl 1,2,8,8a-tetrahydrocyclopropa[c]oxazolo[2,3-e]indol-4-one-6-carboxylate (COI) alkylation subunit.

2. Systematic exploration of the structural features of yatakemycin impacting DNA alkylation and biological activity.

3. A five-membered lactone prodrug of CBI-based analogs of the duocarmycins.

4. Synthesis and evaluation of a series of C5'-substituted duocarmycin SA analogs.

5. Asymmetric total synthesis of (+)- and ent-(-)-yatakemycin and duocarmycin SA: evaluation of yatakemycin key partial structures and its unnatural enantiomer.

6. Efficacious cyclic N-acyl O-amino phenol duocarmycin prodrugs.

7. Insights into conformational changes in AlkD bound to DNA with a yatakemycin adduct from computational simulations.

8. A unique class of duocarmycin and CC-1065 analogues subject to reductive activation.

9. Synthesis and evaluation of a thio analogue of duocarmycin SA.

Review 10. Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065.