(Q33256397)

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:16953635%20AND%20SRC:MED&resulttype=core&format=json

29 December 2019

title

Substituents on quinone methides strongly modulate formation and stability of their nucleophilic adducts (English)

1 reference

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29 December 2019

1

1 reference

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29 December 2019

Mauro Freccero

6

1 reference

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29 December 2019

author name string

Ruggero Dondi

2

1 reference

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29 December 2019

Stefano Colloredo-Melz

3

1 reference

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29 December 2019

Kristen N Frankenfield

4

1 reference

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29 December 2019

Charles H Mitchell

5

1 reference

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29 December 2019

Steven E Rokita

7

1 reference

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29 December 2019

language of work or name

English

0 references

publication date

1 September 2006

1 reference

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:16953635%20AND%20SRC:MED&resulttype=core&format=json

Journal of the American Chemical Society

29 December 2019

published in

1 reference

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29 December 2019

volume

128

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29 December 2019

issue

36

1 reference

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29 December 2019

page(s)

11940-11947

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:16953635%20AND%20SRC:MED&resulttype=core&format=json

The Reactivity–Selectivity Principle: An Imperishable Myth in Organic Chemistry

29 December 2019

cites work

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Quinone methide derivatives: important intermediates to DNA alkylating and DNA cross-linking actions

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Binol quinone methides as bisalkylating and DNA cross-linking agents

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Bioactivation of self-immolative dendritic prodrugs by catalytic antibody 38C2.

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

A general strategy for target-promoted alkylation in biological systems

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

A Transient Product of DNA Alkylation Can Be Stabilized by Binding Localization

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Photohydration and Photosolvolysis of Biphenyl Alkenes and Alcohols via Biphenyl Quinone Methide-type Intermediates and Diarylmethyl Carbocations

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

2'-Deoxyguanosine reacts with a model quinone methide at multiple sites

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Sequence-specific delivery of a quinone methide intermediate to the major groove of DNA.

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Alkylation of amino acids and glutathione in water by o-quinone methide. Reactivity and selectivity

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Reactivity and mutagenicity of endogenous DNA oxopropenylating agents: base propenals, malondialdehyde, and N(epsilon)-oxopropenyllysine.

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Duplex DNA catalyzes the chemical rearrangement of a malondialdehyde deoxyguanosine adduct

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Indirect mutagenesis by oxidative DNA damage: formation of the pyrimidopurinone adduct of deoxyguanosine by base propenal

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Mitomycin C: small, fast and deadly (but very selective)

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

The reversible DNA-alkylating activity of duocarmycin and its analogues

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxy-quinone methides: evidence that extended pi-conjugation dramatically stabilizes the quinone methide formed from eugenol

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

DNA sequence selectivity of guanine-N7 alkylation by nitrogen mustards

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Mechanisms of DNA sequence selective alkylation of guanine-N7 positions by nitrogen mustards

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

The enzymatic formation and chemical reactivity of quinone methides correlate with alkylphenol-induced toxicity in rat hepatocytes.

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Quinone methide formations in the Cu(2+)-induced oxidation of a diterpenone catechol and concurrent damage on DNA.

21 June 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Conjugation of a hairpin pyrrole-imidazole polyamide to a quinone methide for control of DNA cross-linking

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Kinetic and thermodynamic analysis of the hydrolytic ring-opening of the malondialdehyde-deoxyguanosine adduct, 3-(2'-deoxy-beta-D-erythro-pentofuranosyl)- pyrimido[1,2-alpha]purin-10(3H)-one

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Alkylation of guanosine and 2'-deoxyguanosine by o-quinone alpha-(p-anisyl)methide in aqueous solution

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Dendrimer disassembly by benzyl ether depolymerization

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Selectivity of purine alkylation by a quinone methide. Kinetic or thermodynamic control?

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Substituent effects on carbocation stability: the pK(R) for p-quinone methide

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Modeling H-bonding and solvent effects in the alkylation of pyrimidine bases by a prototype quinone methide: a DFT study.

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

A potent, water-soluble and photoinducible DNA cross-linking agent

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Taming reactive phenol tautomers and o-quinone methides with transition metals: a structure-reactivity relationship

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Flash photolytic generation and study of p-quinone methide in aqueous solution. An estimate of rate and equilibrium constants for heterolysis of the carbon-bromine bond in p-hydroxybenzyl bromide

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Flash photolytic generation of o-quinone alpha-phenylmethide and o-quinone alpha-(p-anisyl)methide in aqueous solution and investigation of their reactions in that medium. Saturation of acid-catalyzed hydration

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Thermodynamic versus kinetic products of DNA alkylation as modeled by reaction of deoxyadenosine

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Advances in metal chemistry of quinonoid compounds: new types of interactions between metals and aromatics

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Flash photolytic generation of ortho-quinone methide in aqueous solution and study of its chemistry in that medium

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

Differential rates of reversibility of ecteinascidin 743-DNA covalent adducts from different sequences lead to migration to favored bonding sites

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

4-Hydroxylated metabolites of the antiestrogens tamoxifen and toremifene are metabolized to unusually stable quinone methides.

31 October 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2538442

“Cascade‐Release Dendrimers” Liberate All End Groups upon a Single Triggering Event in the Dendritic Core

31 October 2018

1 reference

12 December 2020

Equilibrium Acidities and Homolytic Bond Dissociation Enthalpies of the Acidic C-H Bonds in P-(Para-substituted benzyl)triphenylphosphonium Cations and Related Cations

1 reference

12 December 2020

A novel approach towards intermolecular stabilization of para-quinone methides. First complexation of the elusive, simplest quinone methide, 4-methylene-2,5-cyclohexadien-1-one

1 reference

12 December 2020

Alkylation of 2'-deoxynucleosides and DNA by quinone methides derived from 2,6-di-tert-butyl-4-methylphenol

1 reference

12 December 2020

Role of glutathione in cellular resistance to alkylating agents

1 reference

12 December 2020

Time-dependent evolution of adducts formed between deoxynucleosides and a model quinone methide

1 reference

12 December 2020

Quinone Methide Alkylation of Deoxycytidine

1 reference

12 December 2020

Identifiers

DOI

10.1021/JA062948K

1 reference

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:16953635%20AND%20SRC:MED&resulttype=core&format=json

29 December 2019

1 reference

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:16953635%20AND%20SRC:MED&resulttype=core&format=json

29 December 2019

PubMed publication ID

16953635

1 reference