Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

Retinoids comprise a group of compounds each composed of three basic parts: a trimethylated cyclohexene ring that is a bulky hydrophobic group, a conjugated tetraene side chain that functions as a linker unit, and a polar carbon-oxygen functional group. Biochemical conversion of carotenoid or other retinoids to retinoic acid (RA) is essential for normal regulation of a wide range of biological processes including development, differentiation, proliferation, and apoptosis. Retinoids regulate various physiological outputs by binding to nuclear receptors called retinoic acid receptors (RARs) and retinoid X receptors (RXRs), which themselves are DNA-binding transcriptional regulators. The functional response of RA and their receptors are modulated by a host of coactivators and corepressors. Retinoids are essential in the development and function of several organ systems; however, deregulated retinoid signaling can contribute to serious diseases. Several natural and synthetic retinoids are in clinical use or undergoing trials for treating specific diseases including cancer. In this review, we provide a broad overview on the importance of retinoids in development and various diseases, highlighting various retinoids in the drug discovery process, ranging all the way from retinoid chemistry to clinical uses and imaging.

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“…Compound 20 containing three methoxy groups in the aromatic ring was compound displaying the most potent anti-proliferative activity. 95 …”

Section: Drug Discovery and Use Of Retinoids For Treatment Of Disementioning

confidence: 99%

Retinoic acid signaling pathways in development and diseases

Das

Thapa

Karki

et al. 2014

Bioorganic & Medicinal Chemistry

224

177

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“…This assay is based on the reduction of WST-1 reagent by viable cells, producing a soluble formazan salt and its absorbance is measured at 450 nm (reference wavelength at 650 nm), as described previously [25], [26]. All results were compared to the internal control of the assay 1% PF-127.…”

Section: Toxicological Assessment Of Cntsmentioning

confidence: 99%

Preparation and Toxicological Assessment of Functionalized Carbon Nanotube-Polymer Hybrids

et al. 2014

Self Cite

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Novel Carbon Nanotube-Polymer Hybrids were synthesized as potential materials for the development of membranes for water treatment applications in the field of Membrane Bioreactors (MBRs). Due to the toxicological concerns regarding the use of nanomaterials in water treatment as well as the rising demand for safe drinking water to protect public health, we studied the functionalization of MWCNTs and Thin-MWCNTs as to control their properties and increase their ability of embedment into porous anisotropic polymeric membranes. Following the growth of the hydrophilic monomer on the surface of the properly functionalized CNTs, that act as initiator for the controlled radical polymerization (ATRP) of sodium styrene sulfonate (SSNa), the antimicrobial quaternized phosphonium and ammonium salts were attached on CNTs-g-PSSNa through non-covalent bonding. In another approach the covalent attachment of quaternized ammonium polymeric moieties of acrylic acid-vinyl benzyl chloride copolymers with N,N-dimethylhexadecylamine (P(AA12-co-VBCHAM)) on functionalized CNTs has also been attempted. Finally, the toxicological assessment in terms of cell viability and cell morphological changes revealed that surface characteristics play a major role in the biological response of functionalized CNTs.

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“…A more convergent strategy was applied to the synthesis of 13 C‐labeled all‐ E ‐retinal 1d , by combining 2 major fragments 9 and 13 (Figure ) 1b, 20, 21 . The fragment containing 2 13 C labels required the phosphonium ylide 14 , which was combined with hydroxyacetone to give the E enoate 15 (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of isotopically labeled all‐trans retinals for DNP‐enhanced solid‐state NMR studies of retinylidene proteins

Leeder

Brown

Becker‐Baldus

et al. 2018

Labelled Comp Radiopharmac

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Three all-trans retinals containing multiple C labels have been synthesized to enable dynamic nuclear polarization enhanced solid-state magic angle spinning NMR studies of novel microbial retinylidene membrane proteins including proteorhodpsin and channelrhodopsin. The synthetic approaches allowed specific introduction of C labels in ring substituents and at different positions in the polyene chain to probe structural features such as ring orientation and interaction of the chromophore with the protein in the ground state and in photointermediates. [10-18- C ]-All-trans-retinal (1b), [12,15- C ]-all-trans-retinal (1c), and [14,15- C ]-all-trans-retinal (1d) were synthesized in in 12, 8, and 7 linear steps from ethyl 2-oxocyclohexanecarboxylate (5) or β-ionone (4), respectively.

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Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

Cited by 31 publications

References 69 publications

Retinoic acid signaling pathways in development and diseases

Retinoic acid signaling pathways in development and diseases

Preparation and Toxicological Assessment of Functionalized Carbon Nanotube-Polymer Hybrids

Synthesis of isotopically labeled all‐trans retinals for DNP‐enhanced solid‐state NMR studies of retinylidene proteins

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