Radiation Sensitization and Chemical Studies on Isoindole-4,7-Diones

Infante, Gabriel A.; González, Pedro; Cruz, Daniel A.; Correa, Jose; Myers, John A.; Ahmad, Mir F.; Whitter, Willie L.; Santos, Alfonso García; Neta, P.

doi:10.2307/3576006

Cited by 13 publications

(5 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ring fusion of pyrrole and p -benzoquinone results in isoindole-4,7-dione (IID, 1 , Figure ), which consequently is a bifunctional molecule and is both a pyrrole and a quinone derivative. Members of the IID group have previously been shown to exhibit pronounced antibacterial activity and have also been considered to be promising radiosensitizers . The bioreductive properties of the IIDs are highly influenced by pH, which renders an investigation thereof very important.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Computational Electrochemistry Study of 16 Isoindole-4,7-diones as Candidates for Organic Cathode Materials

et al. 2012

View full text Add to dashboard Cite

Prediction of the redox behavior of electroactive molecules enables screening of a variety of compounds and can serve as a guideline in the search for organic molecules for use as cathode materials in, for example, Li ion batteries. In this study, we present a computational strategy, based on density functional theory, to calculate redox potentials and acid dissociation constants for a series of 16 isoindole-4,7-dione (IID) derivatives. The calculations take all possible electron and proton transfers into account, and the results were found to correlate very well with electrochemical and spectroscopic measurements. The possibility of polymerizing the IID derivatives was also assessed computationally, as polymerization serves as a straightforward route to immobilize the active material. Three of the considered IIDs (5,6-dicyano-2-methyl-isoindole-4,7-dione, 5,6-dihydroxy-2-methyl-isoindole-4,7-dione, and 2-methyl-5-(trifluoromethyl)-isoindole-4,7-dione) are predicted to be particularly interesting for making polymers for organic cathodes because these are calculated to have high redox potentials and high specific capacities and to be readily polymerizable. The presented strategy is general and can be applied in the prediction of the electrochemical behavior of quinones as well as other systems involving proton and electron transfers.

show abstract

Section: Introductionmentioning

confidence: 99%

“…Members of the IID group have previously been shown to exhibit pronounced antibacterial activity 9 and have also been considered to be promising radiosensitizers. 10 The bioreductive properties of the IIDs are highly influenced by pH, 4 which renders an investigation thereof very important.…”

Section: Introductionmentioning

confidence: 99%

Computational Electrochemistry Study of 16 Isoindole-4,7-diones as Candidates for Organic Cathode Materials

et al. 2012

View full text Add to dashboard Cite

show abstract

“…Their function is closely related to their redox potentials, which enable them to participate in the transport of electrons within the cell membrane. In addition, exogenous quinones are used as antibiotics and antitumor agents in medicine and hold promise as radiosensitizers in the treatment of cancer . These compounds probably either interfere with the complex respiration chain at the cellular level or lead to the liberation of toxic free radicals, which can subsequently attack cellular components, including DNA .…”

Section: Introductionmentioning

confidence: 99%

“…In addition, exogenous quinones are used as antibiotics and antitumor agents in medicine 1 and hold promise as radiosensitizers in the treatment of cancer. 2 These compounds probably either interfere with the complex respiration chain at the cellular level or lead to the liberation of toxic free radicals, which can subsequently attack cellular components, including DNA. 3 Photoinduced electron transfer from DNA has already been established to be an important reaction, which is also responsible for DNA damage.…”

Section: Introductionmentioning

confidence: 99%

Interactions of Guanine and Guanosine Hydrates with Quinones: A Laser Flash Photolysis and Magnetic Field Effect Study

2008

View full text Add to dashboard Cite

Laser flash photolysis and an external magnetic field have been used to study the interaction of two quinone molecules, namely, 9,10-anthraquinone (AQ) and 2-methyl 1,4-naphthoquinone, commonly known as menadione (MQ), with one of the DNA bases, guanine (G) and its nucleoside guanosine hydrate (dG). In organic homogeneous medium, it has been observed that G undergoes a predominant hydrogen (H) abstraction reaction with both the quinones while dG supports photoinduced electron transfer (PET) along with H abstraction. On the other hand, in SDS medium, G supports PET with AQ but not with MQ. However, behavior of dG remains unperturbed toward AQ and MQ with the change in medium. All of these observations have been explained on the basis of stabilization of radical ion pair and difference in size of the quinones, which can affect the distance of approach among the interacting molecules.

show abstract

“…Their function is closely related to their redox potentials which enable them to participate in the transport of electrons within the cell membrane. In addition, exogenous quinones are used as antibiotics and antitumor agents in medicine (Hartly et al, 1988) and hold promise as radiosensitizers in the treatment of cancer (Infante et al, 1982). These compounds probably either interfere with the complex respiration chain at the cellular level or lead to the liberation of toxic free radicals which can subsequently attack cellular components, including DNA (Powis, 1989).…”

Section: Introductionmentioning

confidence: 99%

Quinone Sensitized Electron Transfer Photooxidation of Nucleic Acids: Chemistry of Thymine and Thymidine Radical Cations in Aqueous Solution*

Wagner

Lier

Johnston

1990

Photochem & Photobiology

100

View full text Add to dashboard Cite

The 2-methyl-1,4-naphthoquinone (MQ) sensitized photooxidation of nucleic acid derivatives has been studied by laser flash photolysis and steady state methods. Thymine and thymidine, as well as other DNA model compounds, quench triplet MQ by electron transfer to give MQ radical anions and pyrimidine or purine radical cations. Although the pyrimidine radical cations cannot be directly observed by flash photolysis, the addition of N,N,N',N'-tetramethyl-1,4-phenylenediamine (TMPD) results in the formation of the TMPD radical cation via scavenging of the pyrimidine radical cation. The photooxidation products for thymine and thymidine are shown to result from subsequent chemical reactions of the radical cations in oxygenated aqueous solution. The quantum yield for substrate loss at limiting substrate concentrations is 0.38 for thymine and 0.66 for thymidine. The chemistry of the radical cations involves hydration by water leading to C(6)-OH adduct radicals of the pyrimidine and deprotonation from the N(1) position in thymine and the C(5) methyl group for thymidine. Superoxide ions produced via quenching of the quinone radical anion with oxygen appear to be involved in the formation of thymine and thymidine hydroperoxides and in the reaction with N(1)-thyminyl radicals to regenerate thymine. The effects of pH were examined in the range pH 5-8 in both the presence and absence of superoxide dismutase. Initial C(6)-OH thymine adducts are suggested to dehydrate to give N(1)-thyminyl radicals.

show abstract

Radiation Sensitization and Chemical Studies on Isoindole-4,7-Diones

Cited by 13 publications

References 25 publications

Computational Electrochemistry Study of 16 Isoindole-4,7-diones as Candidates for Organic Cathode Materials

Computational Electrochemistry Study of 16 Isoindole-4,7-diones as Candidates for Organic Cathode Materials

Interactions of Guanine and Guanosine Hydrates with Quinones: A Laser Flash Photolysis and Magnetic Field Effect Study

Quinone Sensitized Electron Transfer Photooxidation of Nucleic Acids: Chemistry of Thymine and Thymidine Radical Cations in Aqueous Solution*

Contact Info

Product

Resources

About