Hydroxymethylfurfural (HMF)
Optimization of 5-hydroxymethylfurfural oxidation via photo-enzymatic cascade process
https://pubs.rsc.org/en/content/articlehtml/2024/gc/d4gc00673a
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Caco-2 cells are an immortalized line of human colorectal adenocarcinoma cells, derived from colon cancer, these cells develop features of mature enterocytes (small intestine cells).
5-Hydroxymethylfurfural (5-HMF) is an organic compound formed in food, particularly through the Maillard reaction, that has been shown to interact with aquaporin-1 (AQP1) channels and demonstrate cytotoxic and absorptive properties in Caco-2 cells (a human colon cancer cell line used to model intestinal absorption).
Metabolic Byproducts: HMF is largely metabolized into 5-hydroxymethyl-2-furoic acid (HMFA).
Mechanism: 5-HMF exhibits antioxidant activity by scavenging free radicals (ABTS and DPPH).
Protective Effects: It has been shown to protect against oxidative damage induced by hydrogen peroxide in cells (PC12 cells) and in in vivo models of ischemia.
Enzyme Modulation: HMF can increase the activities of antioxidant enzymes like superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPx).
Contradictory Evidence: Some studies suggest that in the presence of certain metals, HMF might exhibit pro-oxidative properties.
Biological Activities: Studies show that 5-HMF acts as a modulator of type I IFN-related antiviral immune responses and can suppress inflammatory responses, including blocking the NF-κB/NLRP3 inflammasome pathway in macrophages.
Hair Follicles: The ability of 5-HMF to scavenge radicals and reduce apoptosis induced by hydrogen peroxide suggests it could help protect hair follicles from the inhibitory effects of oxidative stress.
Pharmaceuticals: Furan derivatives are utilized in various medications, including antifungal, antiviral, and anti-inflammatory drugs.
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Thiazoles
Thiazoles are naturally occurring, sulfur-and-nitrogen-containing heterocyclic compounds found in essential vitamins (Vitamin B1/thiamine), firefly luciferin, and various marine/microbial organisms. They are key aroma compounds in cooked foods like peanut butter, coffee, and roasted meats. They are also found in peptides, penicillin, and antioxidants.
Biological Activities:
Naturally occurring thiazoles often exhibit antitumor, antibacterial, antifungal, and anti-inflammatory properties.
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Thiadiazoles are five-membered heterocyclic compounds containing one sulfur and two nitrogen atoms, existing in four isomeric forms. Known for their broad-spectrum pharmacological properties—including antimicrobial, anti-inflammatory, and anticancer activities.
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Thiadiazoles and thiazoles are five-membered heterocycles with nitrogen and sulfur atoms, frequently used in drug design for their anti-inflammatory, anticancer, and antioxidant activities, including inhibition of lipid peroxidation. These compounds act as radical scavengers, reducing oxidative damage caused by reactive oxygen species (ROS).
Anti-inflammatory Mechanism: Thiadiazole/Thiazole derivatives, particularly in the form of 4-thiazolidinones, act as potential anti-inflammatory agents by modulating the HMGB1-RAGE (Receptor for Advanced Glycation End products) and TLR4 signaling pathways.
Inhibition of HMGB1 Release: These compounds can suppress the secretion of HMGB1 from inflammatory cells and directly bind to HMGB1 or its receptors (RAGE/TLR4), blocking downstream activation of NF-κB and MAPK pathways.
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Thiazoles
Tetrahydrofuran (THF)
Furandicarboxylic acid
(FDCA)
Thiadiazolecarboxamide
Carboxamide
Alkaloids
Nicotinamide
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2-Aminothiazole: This is a heterocyclic aromatic compound used in medicinal chemistry to treat various conditions, including prion diseases, neurodegenerative disorders, and as an anti-inflammatory or antibacterial agent. Recent studies have also explored forming novel organosilicon salts using 2-aminothiazole and silanes.
Therapeutic Development: 2-Aminothiazoles are considered "privileged structures" in drug discovery, with applications as antioxidants and neuroprotective agents.
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Compounds:
SW033291
https://en.wikipedia.org/wiki/SW033291
Heteropolymetalate
https://en.wikipedia.org/wiki/Heteropolymetalate
Polyoxometalate
https://en.wikipedia.org/wiki/Polyoxometalate
Phosphotungstic Acid
https://en.wikipedia.org/wiki/Phosphotungstic_acid
Olation
https://en.wikipedia.org/wiki/Olation
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Thiazoles Thiadiazole Carboxamide Heterocyclic Cores Hantzsch Thiazole Synthesis
Hantzsch thiazole synthesis (invented in 1887) is the premier method for creating thiazole rings, a critical 5-membered sulfur/nitrogen heterocycle in drug design. It involves the cyclization of haloketones (or haloaldehydes) with thioamides or thioureas, producing diverse derivatives with high yields for applications like antibacterial agents, HIV drugs, and PROTACs.
Key Aspects of Hantzsch Thiazole Synthesis
Reaction Mechanism: The process begins with a nucleophilic attack of the thioamide sulfur on the carbon of the haloketone, followed by cyclization and dehydration to form the thiazole ring.
Reagents: Commonly uses haloketones/aldehydes, thiourea, or substituted thiosemicarbazones.
Reaction Conditions: Often performed in refluxing solvents (ethanol, acetone). Green chemistry advancements include one-pot, multi-component procedures using, for example, silica-supported tungstosilisic acid.
Applications: Key in creating pharmacological scaffolds, including antifungal, antitumor, and anti-inflammatory compounds.
Thiazole and Thiadiazole Carboxamide Cores
Thiazole: A 5-membered heterocyclic compound present in vitamins (thiamine) and drugs (sulfathiazole, ritonavir).
Thiadiazole Carboxamide: These are heterocyclic derivatives often used as, or incorporated into, pharmacological agents, where the carboxamide functional group attached to the heterocyclic ring enhances bioactivity.
Significance: Thiazole derivatives are used for their rigid structure in designing PROTACs (proteolysis-targeting chimeras) and in constructing highly stable therapeutic molecules.
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Preventing olation, the chemical process where monomeric silicic acid molecules link together to form polymers and eventually insoluble silica gel is critical for maintaining the bioavailability of silicon. Only monomeric, soluble orthosilicic acid (OSA) is readily absorbed by the body.
To prevent olation and keep silica bioavailable, the following methods are effective:
Stabilization with Molecules
Adding stabilizing agents prevents the polymerization of OSA, particularly when concentrations exceed 90 ppm.
Choline: Choline chloride is widely used to stabilize OSA in liquid supplements, preventing it from forming inactive polymerized silica.
Amino Acids/Nutrients: Other molecules can act as stabilizing agents to improve absorption.
Methyl Groups: The addition of a methyl group to form Monomethylsilanetriol (MMST) is a highly effective, stable, and bioavailable form of silicon.
Controlling Concentration and pH
Keep Concentration Low: OSA is stable when diluted. If using solid silica sources, it is recommended to prepare stock solutions no more concentrated than 45g/L to prevent premature gelation.
Lower the pH: Silica polymerization is accelerated at neutral or high pH levels. Maintaining an acidic environment (lower pH) helps prevent the polymerization process.
Order of Mixing: When adding silica (such as AgSil) to nutrient solutions, add the silica to the water first to avoid immediate interaction with nutrients like Calcium (Ca) or Magnesium (Mg), which can cause destabilization.
- Proper Storage and Handling
Prevent Rapid Aging: The polymerization process is often referred to as "aging" of the solution. Rapid sealing and minimizing air exposure can reduce the speed of olation.
Avoid High Temperatures: Increased temperatures can promote silica scaling (polymerization).