Chemistry and Physical Properties of Retinoids

Frickel, Fritz

doi:10.1016/b978-0-12-658101-0.50008-1

Cited by 25 publications

(9 citation statements)

References 422 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[The possible allosteric control of Schiffs base stability has already been suggested on the basis of other experiments with the gecko pigment (Crescitelli and Karvaly, 1989a)l. The next step in this postulated multi-step process is conceived to be a series of chemical reactions in which the nucleophilic addition of cyanide to the terminal carbon of retinal is folllowed by an electrophilic addition of a proton to the adjacent oxygen (Streitweiser and Heathcock, 1981) resulting in retinonitrile or retinal aldehyde cyanohydrin (Conant, 1936, Clark, 1964 (Sporn et al, 1984), a-retinyl ahydroxy acetic acid, a-retinyl lactic acid as well as the more systematic name (all-E)-or (1 l-Z)-4,8-dimethyl-10-(2,6,6-trimethyI-cyclohex-l-en-l-yl)-3-hydroxydeca-5,7,9-tetraenoic acid (Frickel, 1984) all are justified. However, the name a-hydroxy homoretinoic acid seems to describe most accurately the features of the reaction product in the present context and this is why its use is preferred.…”

Section: Discussionmentioning

confidence: 99%

The Visual Pigment Cyanide Effect

Crescitelli

Karvaly

1989

Photochem & Photobiology

View full text Add to dashboard Cite

The visual pigment of the Tokay gecko (Gekko gekko) with its in situ absorption maximum at 521 nm has its spectral position at 500 to 505 nm when chloride-deficient digitonin is used for the extraction. In this case the addition of chloride or bromide to the extract restores the maximum to 521 nm. This property, characteristic of gecko pigments in general, does not occur with any of the rhodopsins that have been tested. Simple salts of cyanide, a pseudohalogenoid with an ionic radius close to those of chloride and bromide and/or its hydrolysis product attacks both this gecko pigment and rhodopsins in the dark. This is seen as a slow thermal loss of photopigment if (sodium) cyanide is present at concentrations above 40 mM for the gecko pigment and 150 mM for the rhodopsins of the midshipman (Porichthys notatus) and of the frog (Rana pipiens). In all cases the loss of the photopigment is accompanied by the appearance of a spectral product with maximum absorption at about 340 nm. Cyanide addition has no effect on the photosensitivity of the native pigments and neither does it alter, as do chloride, bromide and other anions, the spectral absorbance curve. The spectral product at 340 nm also appears when the visual pigments are photolyzed in the presence of cyanide salts below the threshold concentrations given above. Incubation of digitonin-solubilized all-trans-retinal with (sodium) cyanide leads to a reaction product with absorption spectrum similar to that obtained with visual pigments under comparable conditions.(ABSTRACT TRUNCATED AT 250 WORDS)

show abstract

Section: Discussionmentioning

confidence: 99%

The Visual Pigment Cyanide Effect

Crescitelli

Karvaly

1989

Photochem & Photobiology

View full text Add to dashboard Cite

show abstract

“…Cyclodextrin inclusion may protect the guest molecules from their environment and several pharmaceutically interesting compounds show increased stability in the presence of cyclodextrins (Szejtli, 1982;Lerner et al, 1989). Retinal is a member of the retinoid family of compounds (Frickel, 1984). Retinoids are biologically significant compounds because of their roles as essential vitamins, in the photochemistry of vision and in cellular differentiation and proliferation.…”

Section: Introductionmentioning

confidence: 99%

Differentiating inclusion complexes from host molecules by tapping-mode atomic force microscopy

Muñoz-Botella

Martin

Castillo

et al. 1996

Biophysical Journal

View full text Add to dashboard Cite

Tapping-mode atomic force microscopy imaging under different cantilever vibration amplitudes has been used to differentiate the host beta-cyclodextrin nanotubes from retinal/beta-cyclodextrin inclusion complex nanotubes. It was observed that both compounds were deformed differently by the applied probe force because of their different local rigidity. This change in the elasticity properties can be explained as a consequence of the inclusion process. This method shows that tapping-mode atomic force microscopy is an useful tool to map soft sample elasticity properties and to distinguish inclusion complexes from their host molecules on the basis of their different mechanical response.

show abstract

“…The major biologically active retinoid, all-trans retinoic acid, is a metabolite of retinol (vitamin A) (2). Retinol can be stored within lung tissue esterified to fatty acids, where it can be released by retinyl ester hydrolases and then be converted to all-trans retinoic acid (1).…”

mentioning

confidence: 99%

Alveolarization in Retinoic Acid Receptor-β–Deficient Mice

et al. 2005

View full text Add to dashboard Cite

Retinoids bind to nuclear receptors [retinoic acid receptors (RARs) and retinoid X receptors]. RAR␤, one of three isoforms of RARs (␣, ␤, and ␥), is expressed in the fetal and adult lung. We hypothesized that RAR␤ plays a role in alveolarization. Using morphometric analysis, we determined that there was a significant increase in the volume density of airspace in the alveolar region of the lung at 28, 42, and 56 d postnatal age in RAR␤ null mice when compared with wild-type controls. The mean cord length of the respiratory airspaces was increased in RAR␤ null animals at 42 d postnatal age. Respiratory gasexchange surface area per unit lung volume was significantly decreased in RAR␤ null animals at 28, 42, and 56 d postnatal age. In addition, alveolar ducts tended to comprise a greater proportion of the lung airspaces in the RAR␤ null mice. The RAR␤ null mice also had impaired respiratory function when compared with wild-type control mice. There was no effect of RAR␤ gene deletion on lung platelet-derived growth factor (PDGF) receptor ␣ mRNA levels in postnatal lung tissue at several postnatal ages. However PDGF-A protein levels were significantly lower in the RAR␤ null mice than in wild-type controls. Thus, deletion of the RAR␤ gene impairs the formation of the distal airspaces during the postnatal phase of lung maturation in mice via a pathway that may involve PDGF-A. Retinoids regulate the development of the conducting airways and the gas-exchange portion of the lung (1). The major biologically active retinoid, all-trans retinoic acid, is a metabolite of retinol (vitamin A) (2). Retinol can be stored within lung tissue esterified to fatty acids, where it can be released by retinyl ester hydrolases and then be converted to all-trans retinoic acid (1). All-trans retinoic acid binds with high affinity to retinoic acid receptors (RARs), which exist in three isoforms, ␣, ␤, and ␥ (3). Retinoid X receptors (RXRs) primarily bind 9-cis retinoic acid (3). RARs form a heterodimer with RXRs and bind to retinoid responsive elements in target genes (3). RARs and RXRs are members of the steroid hormone receptor superfamily of transcription factors (3).Massaro and co-workers (4,5) reported that all-trans retinoic acid increases the number of alveoli in rat lung. In the first study, postnatal rats that were treated with all-trans retinoic acid had increased numbers of alveoli and increased gas exchange surface area (4). A synthetic glucocorticoid, dexamethasone, decreases the number of alveoli in this animal model. All-trans retinoic acid overcame the inhibitory effects of dexamethasone on alveolarization in the postnatal rats (4). In the second study, elastase was insufflated into the lungs of adult rats to create a model of emphysema, i.e. the damaged lungs in the treated rats were characterized by fewer and larger alveoli and decreased gas exchange area (5). When the elastase-treated rats received an injection of all-trans retinoic acid, the emphysema-like effects of the elastase treatment were almost completely reversed, i...

show abstract

Chemistry and Physical Properties of Retinoids

Cited by 25 publications

References 422 publications

The Visual Pigment Cyanide Effect

The Visual Pigment Cyanide Effect

Differentiating inclusion complexes from host molecules by tapping-mode atomic force microscopy

Alveolarization in Retinoic Acid Receptor-β–Deficient Mice

Contact Info

Product

Resources

About