Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065. (Q37371583)

20 August 2017

1 reference

title

Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065. (English)

1 reference

20 August 2017

Karen S MacMillan

1

1 reference

PMCID

2755654

20 August 2017

Dale L Boger

series ordinal

2

1 reference

PMCID

2755654

20 August 2017

language of work or name

English

0 references

publication date

1 October 2009

1 reference

Journal of Medicinal Chemistry

20 August 2017

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20 August 2017

52

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20 August 2017

19

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20 August 2017

5771-5780

1 reference

An additional spirocyclization for duocarmycin SA

20 August 2017

1 reference

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Total synthesis and evaluation of iso-duocarmycin SA and iso-yatakemycin

6 September 2017

1 reference

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Rational design, synthesis, and evaluation of key analogues of CC-1065 and the duocarmycins

6 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

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

6 September 2017

1 reference

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

6 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

Sequence-selective DNA recognition: natural products and nature's lessons

6 September 2017

1 reference

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Mechanisms of in situ activation for DNA-targeting antitumor agents

6 September 2017

1 reference

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Thiazole orange as the fluorescent intercalator in a high resolution fid assay for determining DNA binding affinity and sequence selectivity of small molecules

6 September 2017

1 reference

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A simple, high-resolution method for establishing DNA binding affinity and sequence selectivity

6 September 2017

1 reference

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Selective metal cation activation of a DNA alkylating agent: synthesis and evaluation of methyl 1,2,9, 9a-Tetrahydrocyclopropa[c]pyrido[3,2-e]indol-4-one-7-carboxylate (CPyI).

6 September 2017

1 reference

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CC-1065 and the duocarmycins: unraveling the keys to a new class of naturally derived DNA alkylating agents

6 September 2017

1 reference

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Duocarmycin A, a new antitumor antibiotic from Streptomyces

6 September 2017

1 reference

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A demonstration of the intrinsic importance of stabilizing hydrophobic binding and non-covalent van der Waals contacts dominant in the non-covalent CC-1065/B-DNA binding

6 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

Structure of the (+)-CC-1065-DNA adduct: critical role of ordered water molecules and implications for involvement of phosphate catalysis in the covalent reaction

6 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

Demonstration of a pronounced effect of noncovalent binding selectivity on the (+)-CC-1065 DNA alkylation and identification of the pharmacophore of the alkylation subunit

6 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

Synthesis and evaluation of N-aryl and N-alkenyl CBI derivatives.

6 September 2017

1 reference

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Solution kinetics of CC-1065 A-ring opening: substituent effects and general acid/base catalysis

14 September 2017

1 reference

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Alkylation of duplex DNA in nucleosome core particles by duocarmycin SA and yatakemycin

2 September 2018

1 reference

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Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin

2 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

Effective asymmetric synthesis of 1,2,9,9a-tetrahydrocyclopropa[c]benzo[e]indol-4-one (CBI).

2 September 2018

1 reference

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Establishing the parabolic relationship between reactivity and activity for derivatives and analogues of the duocarmycin and CC-1065 alkylation subunits

2 September 2018

1 reference

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DNA alkylation properties of yatakemycin

2 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

Establishment of substituent effects in the DNA binding subunit of CBI analogues of the duocarmycins and CC-1065.

2 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

Yatakemycin, a novel antifungal antibiotic produced by Streptomyces sp. TP-A0356.

2 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

The DNA phosphate backbone is not involved in catalysis of the duocarmycin and CC-1065 DNA alkylation reaction.

2 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

A Novel Class of CC-1065 and Duocarmycin Analogues Subject to Mitomycin-Related Reductive Activation

2 September 2018

1 reference

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Are the Duocarmycin and CC-1065 DNA Alkylation Reactions Acid-Catalyzed? Solvolysis pH-Rate Profiles Suggest They Are Not.

2 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

Synthesis and Properties of Substituted CBI Analogs of CC-1065 and the Duocarmycins Incorporating the 7-Methoxy-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (MCBI) Alkylation Subunit: Magnitude of Electronic Effects on the Functional Reactivit

2 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

Metal cation complexation and activation of reversed CPyI analogues of CC-1065 and duocarmycin SA: partitioning the effects of binding and catalysis

2 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

Substituent effects within the DNA binding subunit of CBI analogues of the duocarmycins and CC-1065.

2 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

Synthesis, chemical properties, and biological evaluation of CC-1065 and duocarmycin analogues incorporating the 5-methoxycarbonyl-1,2,9,9a-tetrahydrocyclopropa

2 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

Molecular basis for sequence selective DNA alkylation by (+)- and ent-(-)-CC-1065 and related agents: alkylation site models that accommodate the offset AT-rich adenine N3 alkylation selectivity

2 September 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2755654

CC-1065 and the Duocarmycins: Synthetic Studies

2 September 2018

1 reference

12 December 2020

A fluorescent intercalator displacement assay for establishing DNA binding selectivity and affinity

1 reference

12 December 2020

Yatakemycin: total synthesis, DNA alkylation, and biological properties

1 reference

12 December 2020

Duocarmycin SA, a new antitumor antibiotic from Streptomyces sp

1 reference

12 December 2020

An alternative and convenient strategy for generation of substantial quantities of singly 5'-32P-end-labeled double-stranded DNA for binding studies: development of a protocol for examination of functional features of (+)-CC-1065 and the duocarmycin

1 reference

12 December 2020

Molecular basis for sequence-specific DNA alkylation by CC-1065

1 reference

12 December 2020

CC-1065 (NSC 298223), a potent new antitumor agent improved production and isolation, characterization and antitumor activity

1 reference

12 December 2020

1,2,9,9a-Tetrahydrocyclopropa[c]benz[e]indol-4-one (CBI) analogs of CC-1065 and the duocarmycins: synthesis and evaluation

1 reference

12 December 2020

Demonstration and definition of the noncovalent binding selectivity of agents related to CC-1065 by an affinity cleavage agent: noncovalent binding coincidental with alkylation

1 reference

12 December 2020

Catalysis of the CC-1065 and duocarmycin DNA alkylation reaction: DNA binding induced conformational change in the agent results in activation

1 reference

12 December 2020

Yatakemycin, a Novel Antifungal Antibiotic Produced by Streptomyces sp. TP-A0356.

1 reference

COCI

https://opencitations.net/index/api/v1/citations/10.7164/ANTIBIOTICS.56.107

Duocarmycin A, a new antitumor antibiotic from Streptomyces.

12 April 2024

1 reference

12 April 2024

https://opencitations.net/index/api/v1/citations/10.7164/ANTIBIOTICS.41.1915

Identifiers

DOI

10.1021/JM9006214

1 reference

20 August 2017

1 reference

20 August 2017

1 reference

PMCID

2755654