Acridine dye

Aminacrine hydrochloride 0.1% in a cream caused allergic contact dermatitis on the genitalia of one patient (Wilson 1971). Patch tests with the related substances acriflavine and proflavine were negative. 

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As described in section 4.1, the DNA double helix must unwind to allow access ofthe polymerase enzymes to produce two new strands ofDNA. This is facilitated by DNA gyrase, the target of the quinolones. Some agents interfere with the unwinding of the chromosome by physical obstruction. These include the acridine dyes, of which the topical antiseptic proflavine is the most familiar, and the antimalarial acridine, mepacrine. They prevent strand separation by insertion (intercalation) between base pairs from each strand, but exhibit very poor selective toxicity. 

The acridine dyes, including proflavine, acriflavine and aminacrine, have also been employed for skin disinfection and treatment of infected wounds or burns. They are slow-acting and mainly bacteriostatic in effect, with no useful fungicidal or sporicidal... 

Acridine dyes used as antiseptics, i.e. proflavine and acriflavine, will react specifically with nucleic acids, by fitting into the double helical structure of this unique molecule. In so doing they interfere with its function and can thereby cause cell death. 

Acridine and its derivatives are also fused nitrogen heterocycles similar to acridones, which display a high fluorescence quantum yield and possess the ability to intercalate tightly, though reversively, to the DNA helical structure [73], with large binding constants [74]. As a result, acridine dyes are recognized in the field of the development of probes for nucleic acid structure and conformational determination [75-77]. 

Liu SP, Chen S, Liu ZF et al (2005) Resonance Rayleigh scattering spectra of interaction of sodium carboxymethylcellulose with cationic acridine dyes and their analytical applications. Anal Chim Acta 535 169-175... 

Acridine dyes such as the antimalarial agent quinacrine (Atabrine) shown next are large planar aromatic compounds that intercalate or sandwich themselves between the stacked bases of the helix. 

ACONITATE DECARBOXYASE ACONITATE A-ISOM ERASE Acridine dye intercalation in DNA, SCATCHARD PLOT ACROSIN AcA,... 

Acriflavine proflavine Orange-yellow acridine dye. ACRINOL 0.1% cream. Effective against gram -i-ve bacteria gonococci. Activity enhanced in alkaline medium. Used in chronic ulcers wounds... 

Although the rates of spontaneous mutation are low, they can be greatly increased by mutagenic chemicals (Chapter 27) or by irradiation. It is perfectly practical to measure the rates of both forward and back mutation. When this was done, it was found that certain chemicals, e.g., acridine dyes, induce mutations that undergo reverse mutation at a very much lower frequency than normal. It was eventually shown that these mutations resulted either from deletions of one or more nucleotides from the chain or from insertions of extra nucleotides. Deletion and insertion mutations often result from errors during genetic recombination and repair at times when the DNA chain is broken. 

Acridines, dyes, alkylating Possible binding of chemical agents... 

By bonding two phenyl rings via a heteroatom bridge in the 2- and 2 -positions, the yellow acridine dyes (4a), the red to violet xanthene dyes (4b), or similarly colored thioxanthene dyes (4c) in the case of amino-substituted di- or triaiyl-methane dyes are obtained. Because of their rigid molecular skeletons these compounds fluoresce. Hydroxyxanthenes behave similarly (e.g., fluorescein) [2],... 

Visible light-activated phototropic compositions comprising a hexa-arylbi-imidazole and a bislalkylamino(acridine dye. Cohen, Robert L. (du Pont de Nemours, E. I., and Co.) U.S. 3,563,751 (Cl. 96-90 G 030), 16 Feb 1971, Appl. 20 Jul 1967, 5 pp. Acridine dyes of general formula I, where alkyl R2,R4 = H or... 

Noteworthy exanples are sensitizers such as Ru(bipy)j (29). porphyrins derivatives (30) and acridine dyes, e.g., proflavin (31). Among the electron relay compounds investigated it is worth mentioning the viologens (32) Eu , and their respective salicylate complexes ( ), Ru(bipy)j (3U) and cobalt complexes (35). Thus, at present a considerable choice of sensitizer/relay pairs is available that fulfill the photochemiical and thermodynamic requirements for water decomposition. 

Figure 27.44. Acridines. Acridine dyes induce frameshift mutations by intercalating into the DNA, leading to the incorporation of an additional base on the opposite strand.

Heterodisulfide (CoM-S-S-HTP) reduction - coupled to primary translocation. The reaction in which ATP is synthesized during methanol reduction to CH4 could be identified with energetically competent membrane vesicles of the methanogenic strain G61. These vesicles, which are orientated more than 90% inside-out, catalyzed CH4 formation from CH3-S-C0M by reduction with H2 (Reactions 7,8) and coupled this process with the synthesis of ATP [112]. CH3-S-C0M reduction generated a ApH (inside acidic) as monitored by acridine dye quenching protonophores and ATP synthase inhibitors exerted their effects in accordance with a chemiosmotic type of ATP synthesis [113],... 

Lewis BV, Pybus A, StilweU JH. The oxytocic effect of acridine dyes and their use in terminating mid-trimester pregnancies. J Obstet Gynaecol Br Commonw 1971 78(9) 838-42. 

Acridine dyes used as antiseptics, i.e. proflavine and acriflavine, will react specifically with nucleic acids, by fitting into the double helical structure of this unique molecule. In so doing they interfere with its function and can thereby cause cell death. There is evidence that a depletion of intracellular potassium caused by membrane damage can lead to the activation of latent ribonucleases and the consequent breakdown of RNA. Several biocides, including cetrimide and some phenols, are known to cause the release of nucleotides and nucleosides following an autolytic process. This is irreversible and has been proposed as an autocidal (suicide) process, committing the injured cell to death (Denyer Stewart, 1998). 

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