Interaction between acridine dyes and deoxyribonucleic acid

Armstrong, Ronald W.; Kurucsev, Tomas; Strauss, Ulrich P.

doi:10.1021/ja00713a041

Cited by 209 publications

(66 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…21 The interaction of methylene blue with DNA has been studied with various methods. [22][23][24][25][26] Most studies have indicated that at low ionic strength buffer and low concentration of DNA, the major binding mode of MB with DNA is through intercalation. 24,27 Moreover, MB has a low toxicity.…”

Section: Introductionmentioning

confidence: 99%

Study on the interaction between doxorubicin and Deoxyribonucleic acid with the use of methylene blue as a probe

Hajian

Shams

Mohagheghian

2009

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Neste trabalho, a interação de doxorrubicina com DNA (obtido de timo de bezerro) em fita dupla foi investigada através de técnicas de espectrofotometria UV-Vis, voltametria e espectrofluorometria, usando azul de metrileno (MB) como marcador. O comportamento voltamétrico da doxorrubicina foi investigado em eletrodo de carbono vítreo usando voltametria de pulso diferencial. A doxorrubicina é reduzida, produzindo um pico de redução. Os dois estudos, espectrofotometria UV-Vis e voltametria de pulso diferencial, confirmam a reação de intercalação. Os resultados mostraram que a doxorrubicina e a molécula de MB foram intercaladas na dupla hélice do DNA. A constante de ligação aparente de doxorrubicina com DNA foi 3,2 × 10 4 L mol -1 . O sinal de fluorescência da doxorrubicina e azul de metileno é suprimido com a adição de DNA. A equação de Stern-Volmer baseou-se na supressão do sinal de fluorescência da doxorrubicina.In this work, the interaction of doxorubicin with calf thymus double strand Deoxyribonucleic acid (ds-DNA) has been investigated with the use of Methylene Blue (MB) dye as a probe by the application of UV-Vis spectrophotometry, voltammetry and spectrofluorometry. The voltammetric behavior of doxorubicin has been investigated at glassy carbon electrode using differential pulse voltammetry. Doxorubicin is reduced, yielding one reduction peak. Both UV-Vis spectrophotometry and differential pulse voltammetry studies confirm the intercalation reaction. The results showed that both doxorubicin and the MB molecule could intercalate into the double helix of the DNA. The apparent binding constant of doxorubicin with DNA has been found to be 3.2 × 10 4 L mol -1 . The fluorescence signal of doxorubicin and methylene blue was quenched with DNA addition. The Stern-Volmer equation was plotted based on quenching fluorescence signal of doxorubicin.Keywords: doxorubicin, DNA, chemotherapy, spectrophotometry, voltammetry, spectrofluorometry IntroductionStudy of interactions between drugs and DNA is very interesting and significant not only in understanding the mechanism of interaction, but also for the design of new drugs. 1,2 However mechanism of interactions between drug molecules and DNA is still relatively little known. It is necessary to introduce more simple methods for investigating the mechanism of interaction. By understanding the mechanism of interaction, designing of new DNA-targeted drugs and the screening of these in vitro will be possible.A great variety of substances, including several agents of importance in cancer chemotherapy, 3 are known to bind to DNA by intercalation. 4 Attention has been concentrated on the classical intercalating drugs, acridines and ethidium bromide. [4][5][6] Studies on the binding of various dyes, drugs and antibiotics to DNA and chromatin have contributed to the understanding of the structure of these macromolecules, 6-14 and have suggested possible mechanisms of the biological activity of some drugs. 3 Molecular models of the intercalation of some drugs into DNA have been describ...

show abstract

Section: Introductionmentioning

confidence: 99%

Study on the interaction between doxorubicin and Deoxyribonucleic acid with the use of methylene blue as a probe

Hajian

Shams

Mohagheghian

2009

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…25 The interaction of methylene blue with DNA has been studied with various methods. [26][27][28][29][30] Most studies indicated that (at low ionic strength buffer and low concentration of DNA) the major binding mode of MB with DNA was through intercalation. [28][29][30][31] Moreover, MB has a low toxicity; data from material Safety Data Sheet of Vanderbilt Environmental Health & Safety (VEHS) show that MB is slightly hazardous in case of skin contact, eye contact, ingestion, and inhalation but there is no evidence which shows that MB is a carcinogenic compound.…”

Section: Introductionmentioning

confidence: 99%

Study on the interaction between morin-bi(III) complex and DNA with the use of methylene blue dye as a fluorophor probe

Ensafi

Hajian

Ebrahimi

2009

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Com base em nossa investigação, ambos os complexos, morin-Bi(III) e Morin, podem vincularse ao DNA, embora a natureza da ligação seja diferente para cada um deles. Na presença e ausência do DNA, o morin-Bi(III) mostrou características espectrais diferentes, o que está de acordo com as observadas para outros intercaladores. Neste trabalho, a interação do complexo morin-Bi(III) com o DNA de timo de vitela foi investigada com o uso do azul de metileno (MB), como uma sonda de corante espectral e aplicação de espectrofotometria UV-Vis, espectroscopia de fluorescência e voltametria cíclica. , enquanto que o morin liga-se por um modelo de não-intercalação.Based on our investigation, although both morin-Bi(III) complex and morin can bind to DNA, the nature of the binding was found to be different for each of them. In the presence and absence of the DNA, the morin-Bi(III) complex shows different spectral characteristics which agree with those observed for other intercalators. In this work, the interaction of morin-Bi(III) complex with calf thymus DNA was investigated with the use of methylene blue (MB) dye as a spectral probe and application of UV-Vis spectrophotometry, fluorescence spectroscopy and cyclic voltammetry. The 2:1 morin-Bi(III) complex ratio was calculated by UV-Vis spectroscopy (mole ratio method). The fluorescence signal of Bi(III)-morin complex is increased with DNA addition whereas the fluorescence signal of Morin is decreased with DNA addition. The fluorescence signal of the DNA-complex is quenched by addition of MB which confirms the displacement of the complex with MB. Cyclic voltammetry studies confirm the intercalation reaction. The results showed that only morin-Bi(III) complex can intercalate into the double helix of the DNA. The apparent binding constant of morin-Bi(III) complex with DNA is found to be 2.8 × 10 4 L mol -1, while morin binds in a non-intercalation mode.

show abstract

“…However, preliminary measurements indicate that the dissociation constant ratio for the two types of dye-polymer binding monitored by the present technique is about 100, which is about the binding constant ratio observed for proflavin binding to DNA (15). This fact, together with the different ionic strength dependencies for the two types of dye-polymer binding observed in our experiments ( Table 1), argues that the dye-binding heterogeneity disclosed by the spin-orbital probe technique corresponds to the two-state dye-polymer binding observed by other workers in several dye-polymer systems, as opposed to binding to the two distinct intercalation sites in alternating copolymers like poly(dA-BrdU).…”

Section: Discussionmentioning

confidence: 50%

Spin-Orbital Probes of Biomolecular Structure. A Model DNA-Acridine System

Galley

Purkey

1972

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

Heavy atoms, such as bromine or iodine, perturb the excited-state properties of aromatic chromophores through a spin-orbital coupling mechanism. In the present work the use of specifically directed spinorbital probes to study subtle structural relationships in biopolymers is described. Heavy atoms are introduced into defined sites in biochemical systems and the emission spectrum of a ligand or intrinsic chromophore is monitored for perturbation by the bound heavy atom. This technique is illustrated by a study of acridine dye binding to the copolymer poly(dA-BrdU). The results are interpreted in terms of an "externally" bound dye fraction whose emission is perturbed by the heavy atom in the polymer and an intercalated dye component unperturbed by bromine.The perturbation of electronic excited-state properties of aromatic molecules through a spin-orbital coupling mechanism, mediated by solvent molecules possessing certain heavy atoms as constituents (the so-called "external heavy-atom effect"), was initially observed by Kasha (1). Since that time the influence of solvents containing heavy atoms on the spectroscopic properties of simple molecules has been studied in some detail (2-4). Experimentally, the most accessible manifestations of the external heavy-atom effect are decreases in fluorescence efficiency and phosphorescence lifetime, and an increase in the phosphorescence efficiency of the aromatic molecule. The first of these, fluorescence quenching, has been exploited in biochemical preparations by several investigators who have observed partial fluorescence quenching due to the exposure of a fraction of the emitting molecules to a solvent containing halide ion. This solvent perturbation approach has been used to estimate the number of tryptophyl residues exposed to solvent in proteins (5, 6), and it is capable of distinguishing free proflavin from the dye complexed with DNA (7). Perturbation of thymine phosphorescence by mercuric ion in stoichiometric mercury-polynucleotide complexes has also been reported (8).In The copolymers consisting of alternating adenine and 5-bromouracil deoxyribonucleotides, poly(dA-BrdU), and alternating adenine and thymine deoxyribonucleotides, poly(dAdT), were purchased from General Biochemicals. Poly(dABrdU) was also prepared in this laboratory in a synthesis primed by poly(dA-dT) after the procedure of Riley and Paul (22), with Escherichia coli DNA polymerase generously provided by Dr. David Denhardt, Dept. of Biochemistry, McGill University. Proflavin was a K and K product. Acridine orange was obtained from Eastman. All other materials were of reagent grade. Samples consisted of 0.2-0.3 mM poly(dABrdU) in 0.01 M cacodylic buffer (pH 7.5) diluted 1:1 with an ethylene glycol or glycerol solution of dye. Ionic strengths were adjusted with sodium chloride. Spectra and lifetimes were recorded at 77°K on an instrument already described (23). RESULTSThe changes in phosphorescence that characterize an external heavy-atom perturbation are exemplified by the influence of ethyl b...

show abstract

Interaction between acridine dyes and deoxyribonucleic acid

Cited by 209 publications

References 4 publications

Study on the interaction between doxorubicin and Deoxyribonucleic acid with the use of methylene blue as a probe

Study on the interaction between doxorubicin and Deoxyribonucleic acid with the use of methylene blue as a probe

Study on the interaction between morin-bi(III) complex and DNA with the use of methylene blue dye as a fluorophor probe

Spin-Orbital Probes of Biomolecular Structure. A Model DNA-Acridine System

Contact Info

Product

Resources

About