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PubMed2006

The role of the 11-cis-retinal ring methyl substituents in visual pigment formation.

Artificial visual pigment formation from ring-demethylated retinals was studied in an effort to understand the effect that methyl groups on the chromophore cyclohexenyl ring have on the visual cycle. The stereoselective synthesis of the 11-cis-ring-demethylated analogues involves thallium-accelerated Suzuki cross-coupling reactions and highly stereocontrolled Wittig reactions to form key bonds. Only 11-cis-1,1,5-trisdemethylretinal (2) failed to form an artificial pigment, whilst variable pigment-formation yields were determined for the remaining analogues, increasing with the number (and location) of the chromophore hydrophobic ring methyl groups. Our results with the monodemethylated analogues 11-cis-5-demethylretinal (4) and 11-cis-1-demethylretinal (5) show that the C1-2-CH(3) groups are more important for pigment formation than the C5-CH(3) substituent. This is reflected in the absorption maxima of the artificial pigments, with values closer to that of native rhodopsin for 4. Docking studies based on a rhodopsin crystal structure, however, predict a lower pigment stability for 4 than for 5. Gas-phase DFT (B3LYP/6-31G*) computations of the free-ligand geometries, conformational searches about the C6--C7 bond, and docking studies revealed that, although the conformation of bound 5 is close to that of the native chromophore, the ligand needs to overcome the energy cost of shifting the unbound favored 6-s-trans conformation to the bound 6-s-cis form. In addition, the presence of an extra methyl group at C18 (11-cis-18-methylretinal, 7) is tolerated well and adds further stability to the complex, most probably due to increased hydrophobic interactions.

Binding Sites↗
PubMed1990

Immunolabelling by a newt retinal pigment epithelium antibody during retinal development and regeneration.

The binding of RPE-1, a mouse monoclonal antibody selective for newt retinal pigment epithelium, was followed in eyes undergoing embryonic development and retinal regeneration. Using the indirect immunofluorescence technique on frozen sections, we observed bright and continuous labelling exclusively in the retinal pigment epithelium (RPE) of normal adult newts, but labelling became diminished near the ora serrata region and stopped abruptly at the ciliary margin. During development, labelling was not detected in the retinal pigment epithelium (RPE) until the formation of photoreceptor outer segments and was not observed in any other ocular tissue. There was no correlation between the appearance of pigment in retinal pigment epithelial cells and their labelling with the RPE-1 antibody. Furthermore, albino salamander embryos showed the same pattern of labelling with RPE-1 as that seen in age-matched pigmented animals. During retinal regeneration, RPE cells were labelled less intensely, but heavy labelling was observed in the newly formed retinal cells. With time, labelling in regenerated retina receded, so that by the end of regeneration, labelling by RPE-1 was once more restricted to the RPE cells. The identification of RPE-1 as a marker for postmitotic retinal neurons about to undergo differentiation provides a promising approach for further studies of regeneration with the help of molecular tools.

Albinism↗
PubMed1983

A pigmentation-associated, differentiation antigen of human melanoma defined by a precipitating antibody in human serum.

Antibodies in the serum of melanoma patient AU precipitate an antigen from 125I-labelled extracts of cultured autologous melanoma cells. The antigen, which is probably not a cell surface component, is present in other pigmented melanomas but not in non-pigmented melanomas or other tumor cell types, and the amount of antigen is correlated with the degree of pigmentation. These conclusions are based on absorption experiments with 11 pigmented melanomas, 8 non-pigmented melanomas, 3 astrocytomas, 12 carcinomas of various histological types, I leukemia, 2 EB-virus-transformed B lymphocyte lines, and human erythrocytes. The antigen was also detected in cultured human melanocytes. It has a molecular weight of 70,000, an isoelectric point of pH 5.3, and it binds to concanavalin A-Sepharose. Ninety-six sera from other melanoma patients were examined and none of them precipitated this antigen. As described previously, the serum from patient AU also has antibodies to a unique (Class I) tumor antigen found only on AU melanoma cells. The pigmentation-associated, differentiation antigen and the unique antigen are clearly different in their distribution, but some relationship between these unusual antibody responses is possible.

Antibodies, Neoplasm↗
PubMed1990

Adaptations of visual pigments to the photic environment of the deep sea.

This is a summary of studies that bear on the problems of the adaptation of visual pigments to the photic environment of the deep sea. The results suggest that the spectral absorption of these retinal pigments is shifted toward the blue in order to match the dim, blue-green downwelling light and/or the bioluminescence of organisms that are critical to the life of the species. Through such a spectral match, greater visual sensitivity is achieved for life in the special photic condition of their habitat. This adaptation has been found for chimaerid fishes, for elasmobranchs, for teleosts, for mammals, and for certain crustaceans and cephalopods. The most convincing evidence for such an adaptive match has been found in teleosts that have red-emitting photophores. In these fishes a photopigment with absorbance shifted toward the red has been found by extraction and microspectrophotometry. A few exceptions to this idea of an adaptive match have appeared in the literature, the cone pigments, especially, being examples of such offset pigments. The malacosteid fishes have been shown to have a red-shifted retinal pigment with 11-cis-3-dehydroretinal as the chromophore and some invertebrates have also adopted this molecule to adjust the spectral absorption to the photic environment or to the bioluminescence. These studies are beginning to reveal that visual biochemistry is basically the same in vertebrates and invertebrates and that the visual pigment protein arose early in phylogeny and has been retained, with appropraite modifications, to the present.

Animals↗
PubMed1992

Pulsed dye laser treatment of benign cutaneous pigmented lesions.

Superficial benign cutaneous pigmented lesions that commonly present to the dermatologists and plastic surgeons have been treated by many conventional modalities such as dermabrasion, depigmenting creams as well as several types of lasers. Many of these treatment modalities lack specificity of injury, which has meant that normally pigmented and even non-pigment containing structures such as collagen as well as the hyperpigmented lesion itself have all been indiscriminately destroyed. This has resulted variously in hypopigmentation, hyperpigmentation, in addition to scar formation in some cases. A coaxial 504 nm laser with a pulse duration of 300 nsec was used to treat fifty two patients with superficial benign cutaneous pigmented lesions. Although the number of treatments required to clear the lesion varied according to the type of lesions being treated, on average, between 2 and 4 treatments were required to completely eradicate the superficial benign cutaneous pigmented lesions using 504 nm pulsed dye laser. The skin at the site successfully cleared of the pigmented lesion remained normal in skin color, texture, markings, and mobility.

Child, Preschool↗
PubMed2006

Chemistry and some biological effects of model melanoidins and pigments as Maillard intermediates.

Various pigments were formed in the D-xylose-glycine reaction system. Blue pigments (Blue-M1 and Blue-M2) and red pigments (Red-M1 and Red-M2) were generated in the Maillard reaction. Blue-M2 is presented to have been generated by the reaction between Blue-M1, which involved two pyrrolopyrrole structures as the major blue pigment, and di-D-xyluloseglycine. We identified red pigments as the isomers of addition compounds of D-xyluloseglycine to condensated compound between pyrroropyrrole-2-carbaldehyde and pyrrole-2-carbaldehyde compounds. These pigments have polymerizing activities, suggesting that they are important Maillard reaction intermediates through the formation of melanoidins. Blue-M1 as well as melanoidins effectively suppressed the peroxidation of linoleic acid. The scavenging activity toward Blue-M1 on hydroxyl and DPPH radicals was also as strong as that of melanoidins. Furthermore, Blue-M1 prevents the oxidative cell injury. Therefore, Blue-M1 will be an antioxidant which protects against the oxidative stress in biological systems. Melanoidins induced IFN-gamma mRNA and IL-12 mRNA expressions in spleen cells exposed to allergen and in macrophage-like J774.1 cells, respectively. These findings suggest that melanoidins have suppressive effect on allergic reaction as a novel physiological effect.

Animals↗
PubMed2005

Expression of carotenoid pigments of haloarchaeal cultures exposed to aniline.

The effects of exposure to aniline on growth and pigmentation in three haloarchaeal isolates from the Indian subcontinent--GUSF (MTCC 3265), from the estuarine saltpans of Goa, India; and GURFT-1 and GURFP-1, both from continental shelf sediments of the west coast of India--were studied. In nutrient-rich tryptone yeast extract medium containing 25% NaCl/crude salt, the growth of GUSF, measured as absorbance at 600 nm, was not affected significantly at all concentrations of aniline used [0.005%-0.04% (v/v)], whereas the growth phases of GURFT-1 and GURFP-1 were affected at concentrations > 0.005%; the total yield, however, was nearly equal to the yield of cultures growing in the absence of aniline. GURFT-1 reached approximately 40% of total yield on the 7th day in the presence of 0.04% aniline, which declined thereafter. The pigmentation observed visually was completely abolished at concentrations of aniline greater than 0.01%. Spectral scans of acetone extracts of the pigment of each of the cultures exposed to concentrations of aniline > 0.01% showed that (i) the bacterioruberin component of the pigments (absorbance in the range 390-500 nm) was completely abolished and (ii) the pigment component(s) shifted toward squalene and phytofluene derivatives (320-360 nm). This is the first report examining the effect of an aromatic pollutant such as aniline on the growth and pigmentation of haloarchaeal cultures.

Aniline Compounds↗
PubMed2000

The protease-activated receptor 2 regulates pigmentation via keratinocyte-melanocyte interactions.

Close association exists between melanocytes, the pigment melanin-producing cells in the body, and their neighboring keratinocytes. Keratinocytes are the pigment recipients and skin pigmentation is the result of this interaction. While the chemical basis of melanin production (melanogenesis) is well documented, the molecular mechanism of melanosome transfer needs to be elucidated. We are now providing first evidence that the protease-activated receptor 2 (PAR-2) expressed on keratinocytes, but not on melanocytes, is involved in melanosome transfer and therefore may regulate pigmentation. Activation of PAR-2 with trypsin or with the peptide agonist SLIGRL induced pigmentation in both two- and three-dimensional cocultures of keratinocytes and melanocytes, but not in cocultures that were spatially separated, indicating the need for intimate cell-cell contact. Topical application of SLIGRL on human skin transplanted on SCID mice resulted in a visible skin darkening. Histological examination revealed increased deposits of melanin in the keratinocytes. Inhibition of PAR-2 activation by RWJ-50353, a serine protease inhibitor, resulted in depigmentation and changes in expression of melanogenic-specific genes. Keratinocyte-melanocyte contact was essential for this depigmenting effect. Topical application of this inhibitor induced lightening of the dark skin Yucatan swine, which was confirmed by histochemical analysis. The results presented here suggest a novel mechanism for the regulation of pigmentation, mediated by the activation or inhibition of the keratinocyte receptor PAR-2.

Animals↗
PubMed1997

Light-induced apoptosis: differential timing in the retina and pigment epithelium.

Apoptosis is a genetically regulated form of cell death. Individual cells show condensed nuclear chromatin and cytoplasm, and biochemical analysis reveals fragmentation of the DNA. Ensuing cellular components, apoptotic bodies, are removed by macrophages or neighboring cells. Genes involved in the regulation of apoptosis as well as stimuli and signal transduction systems, are only beginning to be understood in the retina. Therefore, we developed a new in vivo model system for the investigation of events leading to apoptosis in the retina and the pigment epithelium. We induced apoptosis in retinal photoreceptors and the pigment epithelium of albino rats by exposure to 3000 lux of diffuse, cool white fluorescent light for short time periods of up to 120 minutes. Animals were killed at different time intervals during and after light exposure. The eyes were enucleated and the lower central retina was processed for light- and electron microscopy. DNA fragmentation was analysed in situ by TdT-mediated dUTP nick-end labeling (TUNEL) or by gel electrophoresis of total retinal DNA. We observed that the timing of apoptosis in the photoreceptors and pigment epithelium was remarkably different, the pigment epithelium showing a distinct delay of several hours before the onset of apoptosis. In photoreceptors, apoptosis was induced within 90 minutes of light exposure, with the morphological appearance of apoptosis preceding the fragmentation of DNA. In the pigment epithelium, the morphological appearance of apoptosis and DNA fragmentation were coincident. Different regulative mechanisms may lead to apoptotic cell death in the retinal photoreceptors and pigment epithelium. This in vivo model system will allow measurement of dose-responses, a potential spectral dependence and the molecular background of apoptotic mechanisms in the retina.

Animals↗
PubMed2000

Rabbit pigmented ciliary epithelium produces interleukin-6 in response to inflammatory cytokines.

Interleukin-6 is a multifunctional cytokine that is found in high concentrations in intraocular fluids during the uveitic response. Although monocytic cells are a major source of interleukin-6, resident intraocular cells may also contribute to its accumulation in intraocular fluids during uveitis. The purpose of this study was to determine whether interleukin-6 is produced by pigmented ciliary epithelial cells and whether agents known to stimulate interleukin-6 production, such as interleukin-1beta, tumor necrosis factor-alpha, bacterial endotoxin, and stimulators of the adenylyl cyclase/adenosine 3',5'-cyclic monophosphate system, increase interleukin-6 production by these cells. Primary and first-passage cultures of nontransformed rabbit pigmented ciliary epithelial cells were incubated with the test agents for varying periods of time in serum-free medium and interleukin-6 levels in the cell-conditioned medium were measured by bioassay.Little, if any interleukin-6 was released from pigmented ciliary epithelial cells incubated for up to 18 hr in serum-free medium. Interleukin-1betastimulated interleukin-6 release in a time- and concentration-dependent manner. Tumor necrosis factor-alpha, although ineffective alone, increased interleukin-1beta-induced interleukin-6 release in a concentration-dependent manner when co-incubated with interleukin-1betafor 18 hr. However, tumor necrosis factor-alphadid not enhance interleukin-1beta-induced interleukin-6 release if co-incubated with interleukin-1betafor a shorter time (6 hr). A 6 hr exposure to bacterial endotoxin did not stimulate interleukin-6 release from pigmented ciliary epithelial cells. Co-incubation of pigmented ciliary epithelial cells with interleukin-1betaand agents that stimulate the adenyl cyclase/adenosine 3',5'-cyclic monophosphate system through cell surface G-protein transduced receptors, i.e. isoproterenol, vasoactive intestinal peptide or prostaglandin E(2), significantly enhanced the ability of interleukin-1betato stimulate interleukin-6 release. However, neither the adenyl cyclase activator, forskolin or the adenosine 3', 5'-cyclic monophosphate-mimetic, dibutyryl 3',5'-cyclic monophosphate enhanced interleukin-1beta-induced release of interleukin-6. These results indicate that the pigmented ciliary epithelium is one potential source of interleukin-6 and may contribute to the elevation in intraocular fluid interleukin-6 levels observed during various intraocular inflammatory episodes. Although agents that activate the adenyl cyclase/adenosine 3', 5'-cyclic monophosphate system through cell surface G-protein transduced receptors increased interleukin-1beta-induced release of interleukin-6, the ineffectiveness of forskolin and dibutryl 3', 5'-cyclic monophosphate suggest that simply increasing intracellular 3',5'-cyclic monophosphate is not sufficient to augment interleukin-1beta-induced release of interleukin-6. The significance of interleukin-6 in the intraocular inflammatory response is discussed in terms of its proposed role in an endogenous antiinflammatory system acting through induction of interleukin-1 receptor antagonist, soluble tumor necrosis factor receptor, acute-phase proteins and corticosteroids.

Animals↗
PubMed2002

Macular pigment and lutein supplementation in choroideremia.

Choroideremia is an incurable X-linked retinal degeneration caused by mutations in the gene encoding Rab escort protein-1. A group of clinically defined and genotyped patients were studied to determine: (1) the degree of rod and cone dysfunction and structural abnormality in the central retina and the level of macular pigment; and (2) the response of macular pigment and foveal vision to a 6 month trial of supplementation with oral lutein (at 20 mg per day). Rod and cone-mediated function was measured with dark-adapted static perimetry; in vivo retinal structure was determined with optical coherence tomography; and macular pigment optical density was measured with heterochromatic flicker photometry. In this cohort of patients (ages 15-65 years), both rod- and cone-mediated central function declined with age as did central retinal thickness. Macular pigment levels did not differ between patients and male control subjects. Supplementation of oral lutein in a subset of patients led to an increase in serum lutein and macular pigment levels; absolute foveal sensitivity did not change. It is concluded that macular pigment density can be augmented by oral intake of lutein in patients with choroideremia. There was no short-term change in the central vision of the patients on the supplement, but long-term influences of lutein supplementation on disease natural history warrant further study.

Adolescent↗
PubMed2000

Controlled production of active cathepsin D in retinal pigment epithelial cells following adenovirus-mediated gene delivery.

The transduction of a low cathepsin D-producing retinal pigment epithelial cell line with a recombinant adenovirus, Ad.proCatD, carrying a viral promoter and the precursor form of the lysosomal enzyme cathepsin D, procathepsin D, led to the upregulation of proCatD expression. However, the resultant aspartic protease activity did not exceed that observed in normal primary human retinal pigment epithelial cells. Following the injection of Ad. proCatD into rat eyes, immunohistochemistry and Western blot analysis localized the expression of procathepsin D to the retinal pigment epithelial cell layer and to the sclera/choroid/retinal epithelial cell layers, respectively. This upregulation of procathepsin D expression was accompanied by a limited increase in aspartic protease activity. The injected eyes did not demonstrate any of the retinal changes that have been associated with the overproduction and secretion of active cathepsin D. Immunoelectronmicroscopy of Ad.proCatD-transduced retinal pigment epithelial cells demonstrated the presence of cathepsin D not only in cytoplasmic vesicles and lysosomes but also in the nucleoli and, less strongly, elsewhere in euchromatic regions of some 10% of cells. In spite of the upregulated expression of procathepsin D, the production of active cathepsin D in Ad.proCatD-transduced retinal pigment epithelial cells was strictly controlled. It is proposed that active cathepsin D production is controlled at the point of posttranslational modification by an intranuclear feedback mechanism initiated by the relative excess of procathepsin D in Ad. proCatD-transduced retinal pigment epithelial cells.

Adenoviridae↗
PubMed2006

The genetic regulation of pigment cell development.

Pigment cells in developing vertebrates are derived from a transient and pluripotent population of cells called neural crest. The neural crest delaminates from the developing neural tube and overlying ectoderm early in development. The pigment cells are the only derivative to migrate along the dorso-lateral pathway. As they migrate, the precursor pigment cell population differentiates and expands through proliferation and pro-survival processes, ultimately contributing to the coloration of organisms. The types of pigment cells that develop, timing of these processes, and final destination can vary between organisms. Studies from mice, chick, Xenopus, zebrafish, and medaka have led to the identification of many genes that regulate pigment cell development. These include several classes of proteins: transcription factors, transmembrane receptors, and extracellular ligands. This chapter discusses an overview of pigment cell development and the genes that regulate this important process.

Animals↗
PubMed1990

Lipofuscin pigments in the spiral ganglion of the rat.

The purpose of the present study was to clarify morphological differences in lipofuscin or so-called age pigments observed in the spiral ganglion cells of both young and adult rat groups and to characterize the size and structure of ceroid pigment granules generated in vitamin-E-deficient rats. The results showed different patterns of lipofuscin distribution in the two groups. The adult rat group had large aggregated lipoid, dark pigment granules of irregular shape in the cytoplasm. In contrast, the young group had small numbers of small, dense homogeneous granules, suggesting higher Schwann cell phagocytic activity. The ceroid pigments apparently included numerous vesicles and droplets of more variable density and size than the lipofuscin pigments appearing in the non-treated older animals. Both lipofuscin and ceroid pigments developing in such non-dividing cells are produced as a result of peroxidation reactions, so that the more they accumulate in the cytoplasm the more likely cell function deteriorates. The present study has shown that lipofuscin/ceroid granules are generated in the spiral ganglions under either endogenous (aging) or exogenous (vitamin E deficiency) conditions.

Aging↗
PubMed1975

The retinal pigment epithelium and photoreceptor cells. Light- and electron microscopic studies on monkey eyes.

In the perifoveal retina of the monkey, Cercopithecus aethiops, the melanin granules are accumulated in apical cytoplasmatic protrusions of the pigment epithelial cells, facing the end of the cones. The rods are inserted deeper into the pigment epithelium than the cones; they reach the bottom of the infoldings of the apical surface membrane of the pigment epithelial cells. No melanin granules or other inclusions are situated at the end of the rods. The outer extremity of the rods is considerably inclined and in sections often appears as groups of rod discs which are incompletely or completely separated from the main part of the outer segments. This separation is regarded as an artifact caused by the inclination of the rods, and it is therefore not considered to represent phagocytosis of the outer segments by the pigment epithelium. The inclusions of the pigment epithelial cells are classified in five categories which seem to be related to each other owing to their shared structural characteristics. It is suggested that melanin granules are produced, modified and destroyed by the pigment epithelial cells of the adult. Because of the relations between the photoreceptors and the melanin granules it is suggested that light scattered by the melanin granules may pass backwards through the outer segments of the cones, but not of the rods.

Animals↗
PubMed1993

Biosynthesis and cytoplasmic accumulation of a chlorinated catechol pigment during 3-chlorobenzoate aerobic co-metabolism in Pseudomonas fluorescens.

A strain of Pseudomonas fluorescens was capable of co-metabolizing 3-chlorobenzoic acid with the production of a chlorinated catechol black pigment. A peroxidase and another enzymatic activity referred to as a polyphenol oxidase were found to be involved in the oxidation of 4-chlorocatechol to 4-chloro-1,2-benzoquinone, i.e. in the production of highly reactive substrates for pigment formation. Therefore, P. fluorescens cells were seen to take an active part not only in 3-chlorobenzoate mineralization but also in overall pigment production. pH was found to be a key parameter in the regulation of the activity of P. fluorescens oxidoreductive enzymes. Ultrastructural investigations showed that electron dense granules of pigment were distributed throughout the cytoplasm of Pseudomonas fluorescens cells grown in presence of 3-chlorobenzoate, as confirmed also by Thiéry cytochemical investigations. In these cells, an extensive contraction of the cytoplasm as well as a significant damage to the cell wall after two days of incubation, suggested that pigment production caused a premature death of the cells accompanied by the leakage of the cell content. Pigment production seemed to occur mostly in the cytoplasmic context where the electron dense material accumulates until it is released in the medium after the cell lysis.

Aerobiosis↗
PubMed1982

The contribution of pigment transitions to sensitivity changes in the barnacle photoreceptor and the correlation with the prolonged depolarizing afterpotential.

A conditioning light can cause a decrease (adaptation) or an increase (facilitation) in the sensitivity of barnacle photoreceptors, as measured by the amplitude of the late receptor potential (LRP). We show that a net transfer of visual pigment from the rhodopsin (R) to the metarhodopsin (M) state induces a large facilitation whereas the reverse transfer results in a much smaller facilitation or even an adaptation. These effects were not due to the response to the conditioning light but to the pigment reactions. When the conditioning light did not alter the pigment population (i.e., M leads to M, R leads to R) it was followed by an intermediate degree of facilitation. These conclusions are correct for cells which have relatively low sensitivity. In sensitive cells, all pigment transitions produce adaptation. LRP facilitation and the prolonged depolarizing afterpotential (PDA) show several common characteristics with respect to pigment transitions: 1. Their magnitude increases with the amount of pigment transferred from R to M. 2. Both are depressed by the M leads to R transition. 3. Their production is impeded by the M leads to R transition. 4. The PDA itself is facilitated by the R leads to M transition and this facilitation decays with a time course comparable to that of LRP facilitation. These results suggest that there may be an underlying process common to LRP facilitation and PDA.

Animals↗
PubMed1976

Photoelectrochemical effects in the electrolyte-pigment-metal system. II. Metal-free phthalocyanine film action spectra of short-circuit photocurrents with increase of the film thickness.

The electrolyte-pigment-metal system can be described as analogous to a photosensitive junction region. When the thickness of the pigment film is increased, the action spectra of the maximum short-circuit photo-current under continuous illumination differ from the absorption spectra both in direct illumination (pigment-electrolyte) and in back illumination (metal-pigment). One is led to believe that there exist two photoactive regions in the system for the production of the short-circuit photocurrent; these two active regions are associated respectively with each interface. When the metallic semitransparent electrode is made of aluminum the two interfaces have opposite sign contributions to the photocurrent; this allows the determination of conditions in which one can observe specifically the contribution of the pigment-electrolyte interface, that is the interactions between excited pigment molecules and the redox system in the electrolyte.

Action Potentials↗