Efficient syntheses of C(8)-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA.

Efficient syntheses of C(8)-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA. Research Abstract Details 

Research Abstract Table of Contents

Jump to the:

Efficient syntheses of C(8)-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA. Abstract Text:

Qing Dai,Daiwang Xu,Keunpoong Lim,Ronald G Harvey,

The synthesis of the C(8)-aryl adducts of adenine and guanine formed by reaction of the radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAHs), such as benzo[a]pyrene (BP) and dibenzo[def,p]chrysene (DBC), with DNA is reported. The synthetic approach involves in the key step direct reaction of a PAH aldehyde with a di- or triamine precursor of a purine. The method is operationally simple, affords good yields of adducts, and is broad in its scope. The C(8)-aryl adducts of adenine and guanine derived from BP (6-BP-8-Ade and 6-BP-8-Gua) and DBC (10-DBC-8-Ade and 10-DBC-8-Gua) were synthesized in good yields by this method. Analogous C(8)-aryl adenine and guanine derivatives of other PAHs (anthracene, benz[a]anthracene, and chrysene) were also readily prepared via this approach. This method of synthesis is superior to the only method that is currently available. It entails direct reaction of short-lived PAH radical cations (generated electrochemically or chemically) with 2'-deoxyribonucleosides or the corresponding purine bases. It provides the adducts in low yields accompanied by complex mixtures of secondary products. An alternative synthesis that involves Pd-catalyzed Suzuki-Miyaura coupling of arylboronic acids with 8-bromopurine nucleosides was also investigated. Although the C(8)-purine adducts of PAHs, such as naphthalene, phenanthrene, pyrene, and chrysene, could be prepared by this method, analogous adducts of carcinogenic PAHs and other structurally related PAHs, e.g., anthracene, benz[a]anthracene, benzo[a]pyrene, and dibenzo[def,p]chrysene, could not be obtained. This difference was shown to be a consequence of the facility of competing hydrolytic deboronation of the corresponding arylboronic acids.

Efficient syntheses of C(8)-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA. Publishing Authors By Initials

Q Dai,D Xu,K Lim,RG Harvey,

For similar organic chemicals: hydrocarbons: hydrocarbons, cyclic: hydrocarbons, aromatic: polycyclic hydrocarbons, aromatic research abstracts see: organic chemicals: hydrocarbons: hydrocarbons, cyclic: hydrocarbons, aromatic: polycyclic hydrocarbons, aromatic research

PUBMED ID PMID:

MEDLINE DATE:

Efficient syntheses of C(8)-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: The Journal of organic chemistry

VOLUME: 72

Page Numbers: 4856-63

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 27

MONTH: 05

YEAR: 2007

Efficient syntheses of C(8)-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 2985193

Efficient syntheses of C(8)-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA. Keywords Mesh Terms:

KEYWORDS: Polycyclic Hydrocarbons, Aromatic

MESH TERMS: chemistry

Chemical & Substance for Abstract: Efficient syntheses of C(8)-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA. Information

Substance Name: DNA

Registry Number: 9007-49-2

Grant and Affiliation Information for Efficient syntheses of C(8)-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA.

AFFILIATION: The Ben May Department for Cancer Research, The University of Chicago, Chicago, Illinois 60637, USA.

Country: United States

AGENCY: United States NCI

GRANT: CA 92537

ACRONYM: CA

MEDLINETA: J Org Chem

REFSOURCE:

DATABASENAME:

ACCESSION NUMBER:

Number Hits: 0

Efficient syntheses of C8-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA Related Publications

• Addison's disease and the regulation of potassium: the role of insulin and aldosterone.
• An Nkx2-5/Bmp2/Smad1 negative feedback loop controls heart progenitor specification and proliferation.
• Assessment of mobility after multi-level surgery for cerebral palsy.
• Big Brother and AIDS: DKT International vs. USAID.
• Cotesia kariyai larvae need an anchor to emerge from the host Pseudaletia separata.
• DNA organization and thermodynamics during viral packing.
• Deliberate self-harm: emergency department nurses' attitudes, triage and care intentions.
• Development of a retrospective interview measure of parental maltreatment using the Childhood Experience of Care and Abuse (CECA) instrument -- A life-course study of adult chronic depression - 1.
• Effects of noise and distortion on speech quality judgments in normal-hearing and hearing-impaired listeners.
• Efficient syntheses of C(8)-aryl adducts of adenine and guanine formed by reaction of radical cation metabolites of carcinogenic polycyclic aromatic hydrocarbons with DNA.
• Growth hormone and its receptor in projection neurons of the chick visual system: retinofugal and tectobulbar tracts.
• IACUC issues associated with amphibian research.
• Investigation of the Anti-Snake Venom Activity of Schumanniophyton magnificum.
• Mutations in cardiac T-box factor gene TBX20 are associated with diverse cardiac pathologies, including defects of septation and valvulogenesis and cardiomyopathy.
• Neuropsychological impairments in schizophrenia: Integration of performance-based and brain imaging findings.
• Operative technique: the anterior transcallosal transseptal interforniceal approach to the third ventricle and resection of hypothalamic hamartomas.
• Packaging of DNA by bacteriophage epsilon15: structure, forces, and thermodynamics.
• Percutaneous insertion of a proximal humeral locking plate: an anatomic study.
• Perkinsus marinus, a protozoan parasite of the eastern oyster, has a requirement for dietary sterols.
• Pharmacological options for management of opioid dependence.
• Revisiting the Cape Cod bacteria injection experiment using a stochastic modeling approach.
• Self-assessment of functional status in schizophrenia.
• Self-management of a chronic illness: An exploratory study on the role of spirituality among older African American women.
• Small chicken growth hormone (scGH) variant in the neural retina.
• Structural and thermodynamic principles of viral packaging.
• Substituent effects in benz[a]anthracene carbocations: a stable ion, electrophilic substitution (nitration, bromination), and DFT study.
• The importance of transgene and cell type on the regeneration of adult retinal ganglion cell axons within reconstituted bridging grafts.
• Treatment of adult neural progenitor cells prior to transplantation affects graft survival and integration in a neonatal and adult rat model of selective retinal ganglion cell depletion.
• Use of atypical antipsychotic medications in adolescent psychiatric inpatients: a comparison with inpatients who did not receive antipsychotic medications during their stay.
• Validity of retrospective measures of early maltreatment and depressive episodes using the Childhood Experience of Care and Abuse (CECA) instrument -- A life-course study of adult chronic depression - 2.