Hydroxystilbamidine. Nonintercalating drug as a probe of nucleic acid conformation

Festy, B.; Daune, Michel

doi:10.1021/bi00748a003

Cited by 48 publications

(23 citation statements)

References 7 publications

(9 reference statements)

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“…Interestingly, some DNA-binding aromatic diamidines such as berenil, 2-hydroxystilbamidine, and DAPI also exhibit striking fluorescence properties (Bella and Gosálvez, 1994;Stockert et al, 1990b;Murgatroyd, 1982;Kapuscinski and Skoczylas, 1977;Festy and Daune, 1973). Fluorescence microscopy of trypanosomes subjected to berenil treatment (either in culture or isolated from treated animals) revealed a bright blue emission of kinetoplasts and nuclei (Newton, 1975).…”

mentioning

confidence: 99%

A New Fluorescence Reaction in DNA Cytochemistry: Microscopic and Spectroscopic Studies on the Aromatic Diamidino Compound M&B 938

Stockert

Trigoso

Cuéllar

et al. 1997

J Histochem Cytochem.

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We describe the fluorescence properties and cytochemical applications of the aromatic diamidine M&B 938. Treatment of cell smears (chicken blood, Ehrlich ascites tumor, rat bone marrow, mouse mast cells, and Trypanosoma cruzi epimastigotes) with aqueous solutions of M&B 938 (0.5-1 microgram/ml at pH 6-7; UV excitation) induced bright bluish-white fluorescence in DNA-containing structures (interphase and mitotic chromatin, AT-rich kinetoplast DNA of T. cruzi), which was abolished by previous DNA extraction. DNA was the unique fluorescent polyanion after staining with M&B 938 at neutral or alkaline pH, other polyanions such as RNA and heparin showing no emission. M&B 938-stained mouse metaphase chromosomes revealed high fluorescence of the AT-rich centromeric heterochromatin, and strong emission of heterochromatin in human chromosomes 1, 9, 15, 16, and Y was found after distamycin A counterstaining. On agarose gel electrophoresis, M&B 938-stained DNA markers appeared as fluorescent bands. The 1.635-KBP fragment from DNA ladder revealed a higher emission value than that expected from linear regression analysis. Spectroscopic studies showed bathochromic and hyperchromic shifts in the absorption spectrum of M&B 938 complexed with DNA, as well as strong enhancement of fluorescence at 420 nm. In the presence of poly(dA)-poly(dT), the emission of M&B 938 was 4.25-fold higher than with DNA; no fluorescence was observed with poly(dG)-poly(dC). Experimental results and considerations of the chemical structure suggest that the minor groove of AT regions of DNA could be the specific binding site for M&B 938, which shows interesting properties and useful applications as a new DNA fluorochrome.

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confidence: 99%

A New Fluorescence Reaction in DNA Cytochemistry: Microscopic and Spectroscopic Studies on the Aromatic Diamidino Compound M&B 938

Stockert

Trigoso

Cuéllar

et al. 1997

J Histochem Cytochem.

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“…(data not shown) it was found that the addition of 0 .5 mM HSB to the reticulocyte cellfree system completely inhibits fibroin translation. This was not unexpected because HSB has been shown to bind to both DNA and RNA (9) . The fact that polyribosomes isolated from cell lysates prepared in the presence of 1 .5 mM HSB are active in in vitro translation (Fig .…”

Section: Smentioning

confidence: 84%

Isolation of giant silk fibroin polysomes and fibroin mRNP particles using a novel ribonuclease inhibitor, hydroxystilbamidine.

Lizardi¹

1980

The Journal of Cell Biology

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Hydroxystilbamidine isethionate, a dye capable of binding to both DNA and RNA, has been found to be á powerful inhibitor of cellular ribonucleases . A procedure has been developed that, with the aid of this compound, permits the preparative isolation of giant silk fibroin polyribosomes from the posterior silk gland of Bombyx mori . The polyribosomes contain^-45-112 ribosomal particles, as judged by electron microscopy .Treatment of giant fibroin polyribosomes with EDTA releases a particle that sediments at 125S . This mRNP particle contains biologically active silk fibroin mRNA, as judged by cell-free translation in an mRNA-dependent reticulocyte cell-free system .The isolation and characterization of cytoplasmic messenger ribonucleoprotein particles (mRNP) containing specific mRNA's has so far been achieved in relatively few biological systems. The two best studied examples are globin mRNP and myosin mRNP (see reference 1 for review).Insects remain relatively unexploited as model systems for the study ofmRNP structure and function . A promising system for such studies is the posterior silk gland of Bombyx mori, in which silk fibroin mRNA is by far the major mRNA present in the cell.The isolation of fibroin polyribosomes has so far proven difficult because of the lability of the very long mRNA molecule (2-4). In this paper I describe a method that utilizes a novel ribonuclease inhibitor, hydroxystilbamidine isethionate, to achieve the isolation of giant silk gland polyribosomes containing undegraded fibroin mRNA. I also present a preliminary characterization of fibroin-specific mRNP particles obtained from the giant polyribosome fraction . The fibrom mRNA present in these mRNP particles is biologically active . MATERIALS AND METHODSHydroxystilbamidine isethionate was a gift from May and Baker, Ltd., Degenham, Essex, England and from Merrell-National Laboratories, Cincinnati, Ohio. The yellow powder was dissolved in small aliquots in sterile H2O (25-50 mM) and stored up to 4 mo at -20°C in the dark . Sodium heparin was obtained from Sigma Chemical Co., St . Louis, Mo.Silkwork larvae (Gunka x Hushun strain) were raised in the laboratory as described (5). Larvae on the fourth or fifth day of the fifth instar (-4.2 g body weight) were injected with 35 pl of a solution of 10 mg/ml cyclobeximide in H2O. After 5 min, the animals were immobilized in ice, and posterior silk glands were dissected and washed in ice-cold 0.15 M NaCl, 0.015 M Na citrate, 100 hg/ml cycloheximide. Washed glands from two larvae were placed in a Dounce homogenizer (Kontes Co., Vineland, N.J .) containing 4.7 ml of 40 mM triethanolamineHCl, pH 7.5, 0.15 M sucrose, 0.1 M KCI, 3 mM MgClz, 2 mM reduced glutathione, l0 ug/ml cycloheximide, 750 Wg/ml Escherichia coli tRNA, and an appropriate concentration of RNase inhibitor (sodium heparin, 1.5 mg/ml or hydroxystilbamidine isethionate, 1 .5 mM). Homogenization was accomplished by seven slow strokes of a large-clearance Dounce plunger, followed by the addition of 0.3 ml of 2.5 M KCI, 16 .7 mM M...

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“…On the other hand bis(benzamidine)s, e.g. the antineoplastic 6 [22] (Chart 1), bind to the minor groove of helical DNA such that the terminal cationic moieties form ion pairs with phosphate groups of opposite chains while the central portion of the molecule is presented to the interior of the groove [23,24] . Based on these structural requirements, in another effort to obtain more potent and selective compounds we designed and synthesized two new series of derivatives of 1,2,5-oxadiazole N-oxide heterocycle with potential bioreductive cytotoxicity and DNA affinity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of 1,2,5-OxadiazoleN-Oxide Derivatives as Potential Hypoxic Cytotoxins and DNA-Binders

Cerecetto

González

Risso

et al. 2000

Arch. Pharm. Pharm. Med. Chem.

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Several new 1,2,5‐oxadiazole N‐oxide derivatives were synthesized to be tested both as potential selective hypoxic cell cytotoxins and as DNA‐binding agents. The compounds prepared included bis(1,2,5‐oxadiazole N‐oxide) derivatives and oxadiazole rings linked to naphthyl residues. The compounds were tested for their cytotoxicity in oxia and hypoxia and they proved to be non‐selective and less active than the parent compounds 3‐formyl‐4‐phenyl‐1,2,5‐oxadiazole N2‐oxide (3) and 3‐chloromethyl‐4‐phenyl‐1,2,5‐oxadiazole N2‐oxide (4). The DNA‐affinity assays showed that the compounds tested have poor affinity for this biomolecule.

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Hydroxystilbamidine. Nonintercalating drug as a probe of nucleic acid conformation

Cited by 48 publications

References 7 publications

A New Fluorescence Reaction in DNA Cytochemistry: Microscopic and Spectroscopic Studies on the Aromatic Diamidino Compound M&B 938

A New Fluorescence Reaction in DNA Cytochemistry: Microscopic and Spectroscopic Studies on the Aromatic Diamidino Compound M&B 938

Isolation of giant silk fibroin polysomes and fibroin mRNP particles using a novel ribonuclease inhibitor, hydroxystilbamidine.

Synthesis and Biological Evaluation of 1,2,5-OxadiazoleN-Oxide Derivatives as Potential Hypoxic Cytotoxins and DNA-Binders

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