ABSTRACT
Curcumin has been widely used to color textiles but, unlike other natural dyes such as hematoxylin or saffron, it rarely has been discussed as a biological stain. Aspects of the physicochemistry of curcumin relevant to biological staining and self-visualization, i.e., its acidic properties, lipophilicity, metal and pseudometal complexes, and optical properties, are summarized briefly here. Reports of staining of non-living biological specimens in sections and smears, both fixed and unfixed, including specimens embedded in resin, are summarized here. Staining of amyloid, boron and chromatin are outlined and possible reaction mechanisms discussed. Use of curcumin as a vital stain also is described, both in cultured monolayers and in whole organisms. Staining mechanisms are considered especially for the selective uptake of curcumin into cancer cells. Staining with curcumin labeled nanoparticles is discussed. Toxicity and safety issues associated with the dye also are presented.
Subject(s)
Coloring Agents/chemistry , Curcumin/chemistry , Chromatin/chemistry , Cobalt/chemistry , Coordination Complexes/chemistry , HumansABSTRACT
Brief accounts are given of the chemical nature, and past and current biomedical applications of three dyes first synthesized by Raphael Meldola: isamine blue, Meldola's blue and naphthol green B.
Subject(s)
Biomedical Technology , Coloring Agents , Ferric Compounds/chemistry , Naphthalenesulfonates/chemistry , Naphthols/chemistry , Oxazines/chemistry , Rosaniline Dyes/chemistry , Biomedical Technology/history , Biomedical Technology/trends , Coloring Agents/chemical synthesis , Coloring Agents/chemistry , Ferric Compounds/chemical synthesis , History, 19th Century , History, 20th Century , Molecular Structure , Naphthalenesulfonates/chemical synthesis , Naphthols/classification , Rosaniline Dyes/chemical synthesisABSTRACT
The mechanism of selective targeting of the plasma membrane of apoptotic cells by F2N12S, a recently reported ratiometric, fluorescent small molecule probe, was analyzed using decision-rule QSAR models. Selectivity was determined by a combination of the probe's weak amphiphilicity and slow flip-flop with the increased plasma membrane fluidity of apoptotic cells. The probable chemical features required for such probes may be defined in terms of numerical structural parameters as: 3.5 < AI < â¼ 5.5; log P < 5.0; HGS > 400 (where AI, log P and HGS parameters model amphiphilicity, lipophilicity and headgroup size, respectively). When HGS is <400, compounds are initially membrane selective, but subsequently are internalized.
Subject(s)
Apoptosis , Cell Membrane/chemistry , Flavonoids/analysis , Flavonoids/chemistry , Fluorescent Dyes/analysis , Fluorescent Dyes/chemistry , Cell Line , Cell Membrane/metabolism , Humans , Membrane Fluidity , Molecular Structure , Quantitative Structure-Activity Relationship , Spectrometry, Fluorescence , Staining and LabelingABSTRACT
A novel technique developed in the laboratories of Bradley D. Smith and David Piwnica-Worms for imaging bacterial infections in intact living nude mice using a novel fluorescent dye, a conjugate of a NIR carbocyanine dye and two zinc(II) dipicolylamine units, allows relatively deep imaging of bacterial infection in real time. The behavior of the mice indicated good tolerance of the probe. The probe's water-octanol partition coefficient calculated by Hansch and Leo's procedure demonstrates that it is slightly lipophilic and therefore could enter mouse cells. Extant values of the physicochemical and spectroscopic parameters relevant to practical use are tabulated.
Subject(s)
Escherichia coli/isolation & purification , Staphylococcus aureus/isolation & purification , Tomography, Optical/methods , Animals , Fluorescent Dyes , Mice , Mice, Inbred Strains , Organometallic Compounds , Picolines , Sensitivity and Specificity , Spectroscopy, Near-Infrared/methods , Staphylococcal Infections/diagnosis , Staphylococcal Infections/microbiologyABSTRACT
The use of C12-nitrobenzofuran-conjugated phosphatidylcholine (NBD-PC) for staining intracellular lipid in the form of membrane lamellae present in cultured cell monolayers, which recently was reported by Kasahara et al., is summarized and commented on. This is the first report of this fluorochrome's application as a "dye" rather than as a fluorescent lipid analogue. Analysis using the log P parameter suggests that the observed efficacy of the C12 form, compared to the non-staining character of the C6 form, may be attributed to insufficient partitioning of the latter into lipid. Confusion of the terms "dye" or "stain" and "fluorescent lipid analogue" in the current literature is addressed here. Optical and other physicochemical properties of the stain useful for practical laboratory purposes are summarized from various sources.
