Comparative binding of ethidium and three azido analogs to dinucleotides: affinity and intercalation geometry. A 1H NMR and visible spectroscopy study.
AuthorsLaugaa P, Delbarre A, Le Pecq JB, Roques BP
JournalEur J Biochem
PubMed ID6861758
'Geometrical and thermodynamic information has been obtained from theoretical analysis of both visible and 1H-NMR spectroscopic binding isotherms of ethidium and three photoactivable derivatives (8-azido-ethidium, 3-azido-ethidium and 3,8-diazido-ethidium) to self-complementary ribodinucleosides. The following results have been obtained. 1. Interaction with pyrimidine(3-5'')purine sequences is well accounted for by multicomponent equilibria involving ... More
Ligand binding sites and subunit interactions of Torpedo californica acetylcholine receptor.
AuthorsWitzemann V, Raftery M
JournalBiochemistry
PubMed ID687601
'A [3H]bisazido derivative of ethidium bromide was synthesized to identify sites of interaction of ethidium with the acetylcholine receptor from Torpedo californica and to aid in localization of ligand binding sites. For purified solubilized acetylcholine receptor it was shown (a) that the photolabel was competitive with ethidium bromide, (b) dodecyl ... More
Covalent binding of ethidium azide analogs to Salmonella DNA in vivo: competition by ethidium bromide.
AuthorsYielding LW, Graves DE, Brown BR, Yielding KL
JournalBiochem Biophys Res Commun
PubMed ID444231
Ethidium bromide and its photoreactive analogues: spectroscopic analysis of deoxyribonucleic acid binding properties.
AuthorsGraves DE, Watkins CL, Yielding LW
JournalBiochemistry
PubMed ID7225364
Nuclear mutations and mitotic recombination in Saccharomyces by light-activated ethidium azides.
AuthorsHixon SC, Burnham D
JournalMutat Res
PubMed ID379634
Cross-linking of double-helical nucleic acids with a photoreactive analogue of ethidium.
AuthorsWoolley P, Dohrmann S
JournalBiochemistry
PubMed ID6882746
Intercalation of the ethidium analogue 3,5-diazido-5-ethyl-6-phenylphenanthridinium into double helices followed by irradiation with blue or ultraviolet light results in cross-linking between the two strands with an efficiency around 30% for DNA, RNA, and DNA-RNA hybrids. Details of this reaction and a convenient synthesis of the ethidium analogue are described. Stable ... More
[Structure-function characterization of phenanthridinium compounds as mutagens in salmonella and yeast]
AuthorsFukunaga M, Matsumoto N, Matsushita T, Mizuguchi Y
JournalJ UOEH
PubMed ID6385182
The relation between the mutagenic activities and chemical structure of phenanthridinium derivatives were tested by using Salmonella typhimurium strain TA 98 and yeast Saccharomyces cerevisiae. The 3,8-diamino analog and amino-azido isomers caused frameshift type mutation in Salmonella. However, mutagenicity was severely reduced for the diazido analog, and mutagenic activities of ... More
Synthesis, separation and characterization of the mono- and diazide analogs of ethidium bromide.
AuthorsGraves DE, Yielding LW, Watkins CL, Yielding KL
JournalBiochim Biophys Acta
PubMed ID911852
Ethidium bromide is used to characterize nucleic acid secondary and tertiary structural properties and the biological consequences of drug interactions. The mono- and diazido analogs of ethidium have proven valuable as photoaffinity probes in chemical and biological studies on nucleic acids, since they render the ethidium-nucleic acid interaction covalent. Although ... More
Photofootprinting of drug-binding sites on DNA using diazo- and azido-9-aminoacridine derivatives.
AuthorsJeppesen C, Nielsen PE
JournalEur J Biochem
PubMed ID2472274
It is demonstrated that DNA photofootprinting analysis of the intercalating depsipeptide echinomycin, and the minor groove-binders distamicyn, 4',6-diamidino-2-phenylindole (DAPI) and Hoechst 33258 can be performed using 9-[6-(2-diazocyclopentadienylcarbonyloxy)hexylamino]acridine (DHA) [Nielsen et al. (1988) Nucleic Acids Res. 16, 3877-3888] or 2-methoxy-6-azido-9-aminoacridine (MAA) [Jeppesen et al. (1988) Nucleic Acids Res. 16, 5755-5770]. Both ... More
Petite induction in Saccharomyces cerevisiae by ethidium analogs: distinction between resting and growing cells.
AuthorsFukunaga M, Yielding LW, Firth WJ, Yielding KL
JournalMutat Res
PubMed ID6993943
The importance of specific substituents, especially amino azide groups, for ethidium induction of petites was evaluated in resting and dividing cells of Saccharomyces cerevisiae through the study of a series of ethidium analogs. The structural requirements in resting and growing cells were found to be different, suggesting that at least ... More
Use of diazido ethidium bromide as a specific probe for mitochondrial functions.
AuthorsBastos RN
JournalJ Biol Chem
PubMed ID126240
The diazido derivative of ethidium bromide has been synthesized as a potential photoaffinity label and shown to be at least as effective as a mitochondrial mutagen as the parent compound, with a similar mode of action. Exposure of mitochondria of Saccharomyces cerevisiae to the compound, followed by ultraviolet-irradiation, which converts ... More
Ethidium bromide enhancement of frameshift mutagenesis caused by photoactivatable ethidium analogs.
AuthorsYielding LW, Brown BR, Graves DE, Yielding KL
JournalMutat Res
PubMed ID392307
Ethidium azide analogs (3-amino-8-azido-ethidium monoazide and ethidium diazide) have been developed as photosensitive probes in order to analyze directly the reversible in vivo interactions of ethidium bromide. Our preliminary observations [11], relating the mutagenic potential of the monoazide analog of ethidium, have been extended and refined, using the highly purified ... More
Structure-function characterization for ethidium photoaffinity labels as mutagens in Salmonella.
AuthorsYielding LW, Firth WJ
JournalMutat Res
PubMed ID6993933
The development of photoaffinity probes to characterize the binding process and subsequent biological activity of a drug has recently been emphasized by the synthesis of two ethidium azide analogs. The initial finding showed that one of the azido analogs, the 8-azido-3-amino derivative, was at least 40-fold more mutagenic and toxic ... More
Site-selective photoaffinity labeling of the Torpedo californica nicotinic acetylcholine receptor by azide derivatives of ethidium bromide.
AuthorsPedersen SE
JournalMol Pharmacol
PubMed ID7838117
Three azido derivatives of ethidium bromide, a potent noncompetitive antagonist of the nicotinic acetylcholine receptor from Torpedo californica, were synthesized, namely 8-azido-ethidium chloride, 3-azido-ethidium chloride, and 3,8-diazido-ethidium chloride. These derivatives were tested for their ability to interact with the noncompetitive antagonist binding site and the acetylcholine binding sites on the ... More