Retinoid Structure, Chemistry, and Biologically Active Derivatives

Curley, Robert W.; Robarge, Michael J.

doi:10.1016/s1569-2590(08)60051-8

Cited by 4 publications

(3 citation statements)

References 143 publications

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“…The higher phototoxicity observed for porphyrin−retinamides 2 and 3 which accumulated to a significantly smaller extent within cells than conjugates 4 and 5 , and in addition localized mainly within the cell lysosomes, while 4 and 5 were also found in the more sensitive ER, suggests that these porphyrin−retinamides induce cell death via different mechanisms. Previous studies have shown that retinoids are capable of mediating apoptosis, although the biological mechanisms leading to retinoid-induced cell death are poorly understood ( , ). It is possible that, upon light exposure, the lysosomal content is released into the cytoplasm where the hydrophobic porphyrin−retinamides 2 and 3 preferentially bind the CRABPs proteins in comparison with the more hydrophilic conjugates 4 and 5 .…”

Section: Discussionmentioning

confidence: 99%

“…Nuclear receptors consist of a vast family of proteins composed of steroid receptors, nonsteroidal receptors, thyroid hormone receptors, and retinoic acid receptors, all of which play a major role in intracellular signaling and carcinogenesis ( , ). Among these, the retinoic acid receptor (RAR) and the retinoic X receptor (RXR) belong to a large family of proteins that activate transcription in the presence of retinoic acids, the biologically active metabolites of vitamin A (retinol) and its active derivatives ( , ). The use of retinoids to suppress tumor development has been evaluated in animal models of carcinogenesis including skin, breast, oral cavity, lung, hepatic, gastrointestinal, prostate, and bladder cancers ( − ).…”

Section: Introductionmentioning

confidence: 99%

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Porphyrin−Retinamides: Synthesis and Cellular Studies

Sibrian‐Vazquez

2007

Bioconjugate Chem.

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A series of four porphyrin-retinamides containing either all-trans- or 13-cis-retinoid acid residues, directly linked to the para-phenyl position of meso-tetraphenylporphyrin or via a low-molecular-weight PEG spacer, have been synthesized. The biological properties of these conjugates were evaluated in a model cell line, human HEp2, and in neuroblastoma SK-N-DZ cells, which exhibit moderate expression of retinoic acid receptors and retinoic acid-induced differentiation. The directly linked porphyrin-retinamides were taken up by a greater extent (20-50% more) in SK-N-DZ than in HEp2 cells. However, the PEG-containing conjugates accumulated maximally within both cell lines and approximately by the same amount, probably due to their increased amphiphilicity. Among all conjugates, the porphyrin-PEG-13-cis-retinamide accumulated the most in both cell lines (about 5 times more than the non-pegylated conjugates). None of the porphyrin-retinamide conjugates were toxic toward HEp2 cells at concentrations up to 100 microM, and only the hydrophobic non-pegylated conjugates were moderately toxic to SK-N-DZ cells [IC50 (dark) = 56-92 microM, and IC50 (at 1 J/cm2) = 6-8 microM]. All conjugates preferentially localized within cellular vesicles that correlated well to the lysosomes and, in addition, the PEG-containing porphyrin-retinamides were also found in the ER.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Porphyrin−Retinamides: Synthesis and Cellular Studies

Sibrian‐Vazquez

2007

Bioconjugate Chem.

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“…The primary molecules with critical functions are retinol (vitamin A) and retinoic acid, followed by the oxidized form of retinol, with the most common isomers being all trans-retinoic acid (AT-RA) and 9-cis retinoic acid (9-cis-RA) [114,115]. RA is known chemically as 3,7-dimethyl-9-(2,6,6-trimethyl-lcyclohexen-l-yl)-2,4,6,8-nonatetaenoic acid (Figure 4) [116].…”

Section: Retinoic Acid (Ra)mentioning

confidence: 99%

Synergistic Effect of Retinoic Acid and Lactoferrin in the Maintenance of Gut Homeostasis

Peña-Juárez,

Guadarrama-Escobar,

Serrano-Castañeda

et al. 2024

Biomolecules

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Lactoferrin (LF) is a glycoprotein that binds to iron ions (Fe2+) and other metallic ions, such as Mg2+, Zn2+, and Cu2+, and has antibacterial and immunomodulatory properties. The antibacterial properties of LF are due to its ability to sequester iron. The immunomodulatory capability of LF promotes homeostasis in the enteric environment, acting directly on the beneficial microbiota. LF can modulate antigen-presenting cell (APC) biology, including migration and cell activation. Nonetheless, some gut microbiota strains produce toxic metabolites, and APCs are responsible for initiating the process that inhibits the inflammatory response against them. Thus, eliminating harmful strains lowers the risk of inducing chronic inflammation, and consequently, metabolic disease, which can progress to type 2 diabetes mellitus (T2DM). LF and retinoic acid (RA) exhibit immunomodulatory properties such as decreasing cytokine production, thus modifying the inflammatory response. Their activities have been observed both in vitro and in vivo. The combined, simultaneous effect of these molecules has not been studied; however, the synergistic effect of LF and RA may be employed for enhancing the secretion of humoral factors, such as IgA. We speculate that the combination of LF and RA could be a potential prophylactic alternative for the treatment of metabolic dysregulations such as T2DM. The present review focuses on the importance of a healthy diet for a balanced gut and describes how probiotics and prebiotics with immunomodulatory activity as well as inductors of differentiation and cell proliferation could be acquired directly from the diet or indirectly through the oral administration of formulations aimed to maintain gut health or restore a eubiotic state in an intestinal environment that has been dysregulated by external factors such as stress and a high-fat diet.

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