Isotope-Labeled Compounds

Tolcapone-d4 is a deuterated derivative of the selective catechol-O-methyltransferase (COMT) inhibitor, Tolcapone. This compound exhibits an IC50 of 773 nM, demonstrating its potency in inhibiting COMT activity. Tolcapone-d4 is utilized in research related to neurodegenerative disorders and cancer, as it influences α-synuclein and amyloid-beta oligomerization and fibrillogenesis. Additionally, it has been shown to induce oxidative stress, promote apoptosis in cancer cells, and increase reactive oxygen species (ROS) production, making it valuable for studies in both cancer and neurological disease contexts.

Colchicine-d3 is a deuterium-labeled derivative of colchicine, a potent inhibitor of tubulin that disrupts microtubule dynamics. It exerts its primary biological activity by inhibiting microtubule polymerization at an IC50 of 3 nM. Additionally, colchicine acts as a competitive antagonist of α3 glycine receptors (GlyRs), making it valuable for various research applications in cell biology and neurobiology.

Triclosan-13C12 is a stable isotope-labeled form of Triclosan, a potent broad-spectrum antibacterial agent that targets the enoyl-acyl carrier protein reductase (FabI) involved in bacterial fatty acid synthesis. This compound exhibits inhibitory activity against E. coli FabI with IC50 values of 2 μM and 10 μM for the wild-type and FabIG93V variants, respectively. Additionally, Triclosan has been shown to induce apoptosis in cultured rat neural stem cells and to exacerbate colitis and colitis-associated colorectal tumorigenesis in various animal models. This reagent is valuable for studies involving metabolic tracking and the investigation of antibiotic mechanisms.

Enterolactone-d6 is a deuterium-labeled form of Enterolactone, a bioactive phenolic metabolite classified as a mammalian lignan derived from dietary sources. Enterolactone exhibits estrogenic activity and has demonstrated anti-breast cancer effects, functioning as a radiosensitizer by impairing DNA repair mechanisms and promoting increased apoptosis in human breast cancer cell lines. This stable isotope is valuable for metabolic studies and research exploring the biological pathways and effects of lignans.

L-Histidine-13C6 hydrochloride hydrate is a stable isotope-labeled form of L-Histidine, used primarily in metabolic research and tracer studies. This compound serves as an endogenous metabolite that can scavenge hydroxyl radicals and singlet oxygen, demonstrating notable anti-inflammatory and antioxidant properties. Additionally, it plays a role in the regulation of essential metal ion absorption, including zinc, copper, and iron, and is capable of penetrating the blood-brain barrier, making it valuable for neurobiological investigations.

Paclitaxel-d5 (benzoyloxy) is a deuterium-labeled derivative of the antineoplastic agent Paclitaxel. It primarily targets tubulin, enhancing polymerization stability, which leads to mitotic arrest and promotes apoptotic pathways. Additionally, Paclitaxel-d5 has been shown to induce autophagy, making it valuable for research applications focused on cancer biology and cellular response mechanisms.

Vincristine-d3-1 sulfate is a deuterium-labeled derivative of Vincristine sulfate, a potent antitumor vinca alkaloid. It acts by inhibiting microtubule polymerization, leading to cell cycle arrest at the metaphase stage, which is critical in cancer treatment. With a Ki of 85 nM for microtubule binding, this stable isotope is valuable for mechanistic studies and quantitative applications in cancer research.

Vorinostat-d5 is a deuterium-labeled form of Vorinostat, a potent pan-inhibitor of histone deacetylases (HDACs), specifically targeting HDAC1, HDAC2, and HDAC3 (Class I), HDAC7 (Class II), and HDAC11 (Class IV), with ID50 values of 10 nM and 20 nM for HDAC1 and HDAC3, respectively. It effectively induces apoptosis in cancer cells and serves as an inhibitor of human papillomavirus (HPV)-18 DNA amplification. Vorinostat-d5 is valuable for research applications focused on epigenetics, cancer therapy, and virology.

Camptothecin-d5 is a deuterium-labeled derivative of Camptothecin, a potent inhibitor of DNA topoisomerase I with an IC50 of 679 nM. This compound exhibits significant antineoplastic activity against various cancers, including colorectal, breast, lung, and ovarian malignancies. Additionally, Camptothecin modulates hypoxia-inducible factor-1α (HIF-1α) activity by altering microRNA expression patterns in human cancer cells, making it valuable for cancer research applications.

5-Fluorouracil-15N2 is a stable isotope-labeled analogue of the chemotherapeutic agent 5-Fluorouracil (5-FU). It primarily targets thymidylate synthetase, inhibiting pyrimidine synthesis and leading to decreased intracellular dTTP levels, which induces apoptosis in cancer cells. Additionally, it has been noted for its potential to serve as a chemical sensitizer and exhibits inhibitory effects on HIV. This compound is valuable for research applications in cancer therapy and HIV studies.

Chlorhexidine-d8 dihydrochloride is a deuterated form of the cationic antimicrobial agent chlorhexidine, which specifically targets microbial cell membranes. It exhibits broad-spectrum bactericidal activity against both Gram-positive and Gram-negative bacteria by binding non-specifically to cell membrane phospholipids, disrupting membrane integrity, and causing the leakage of cellular contents. This compound is valuable for research applications exploring antimicrobial mechanisms, membrane permeability, and the effects of antimicrobial agents on microbial physiology and cell death pathways.

Thiamine-d3 hydrochloride is a deuterated form of Thiamine hydrochloride, serving as a stable isotope in metabolic studies. Thiamine is a vital micronutrient that acts as a cofactor for numerous central metabolic enzymes, playing a crucial role in carbohydrate metabolism. This labeled compound is particularly valuable in biological research applications such as tracer studies, metabolic flux analysis, and the investigation of thiamine-related metabolic pathways.

(Rac)-Hesperetin-13C,d3 is a deuterium- and carbon-13 labeled derivative of (Rac)-Hesperetin, the racemic form of the natural flavanone Hesperetin. This compound serves as a stable isotope for metabolic studies and provides a valuable tool for elucidating the role of UGT enzymes, as Hesperetin is known to be a potent inhibitor of human UGT activity. Additionally, (Rac)-Hesperetin displays pro-apoptotic effects through the activation of the p38 MAPK pathway, offering insights into its potential biological mechanisms.

D-Mannitol-13C6 is a stable isotope-labeled form of D-Mannitol, targeting metabolic pathways through its role as an osmotic agent. This compound is utilized in various research applications, including studies on calcium and magnesium absorption, cecal fermentation, and the modulation of insulin sensitivity. D-Mannitol has been shown to promote the browning of white adipose tissue by activating the β3-adrenergic receptor, which can lead to enhanced thermogenesis and potential reductions in blood glucose levels. Additionally, it is employed in plant cell culture to maintain osmotic balance and protect cellular integrity.

D-Mannitol-13C is a stable isotope-labeled derivative of D-Mannitol. This compound serves as a valuable osmotic diuretic and is utilized in various research applications, including the study of calcium and magnesium absorption and retention through cecal fermentation. D-Mannitol is known to promote brown adipose tissue formation, enhance insulin sensitivity, and lower blood glucose levels by activating the β3-adrenergic receptor, leading to the conversion of white fat cells into brown fat cells. Additionally, it is employed to maintain osmotic pressure in plant cell cultures, aiding in cellular protection during physiological manipulation.

Lenalidomide-d5 is a stable isotope-labeled derivative of Lenalidomide, an immunomodulatory compound that functions as a molecular glue. By acting as a ligand for the ubiquitin E3 ligase cereblon (CRBN), it facilitates the selective ubiquitination and subsequent degradation of the transcription factors IKZF1 and IKZF3. Lenalidomide-d5 is pivotal for research in cancer biology, particularly for investigating the mechanisms of action in mature B-cell lymphomas, including multiple myeloma, and for studying its effects on cytokine release from T cells.

Oxybenzone-d5 is a deuterium-labeled analogue of Oxybenzone, which functions primarily as a UV filter in various personal care products. This compound has been identified as an endocrine-disrupting chemical (EDC), capable of traversing the placental and blood-brain barriers. Oxybenzone-d5 is valuable for studying the effects of EDCs, as it plays a role in impairing autophagy, modifying epigenetic states, and disrupting retinoid X receptor signaling in apoptotic neuronal cells, making it useful in toxicology and pharmacology research.

Glyphosate-d2 is a deuterium-labeled form of Glyphosate, an herbicide derived from the amino acid glycine. It specifically inhibits the enzyme 5-enolpyruvylshikimate-3-phosphate synthase within the shikimate pathway, a metabolic route essential for the biosynthesis of aromatic amino acids in plants. This stable isotope is valuable for research applications including environmental monitoring and metabolic studies to trace glyphosate's behavior in ecological systems.

Diclofenac-13C6 sodium is a stable isotope-labeled derivative of Diclofenac, a potent and nonselective inhibitor of cyclooxygenases (COX-1 and COX-2). With IC50 values of 4 nM and 1.3 nM in human CHO cells, it exhibits strong anti-inflammatory activity. Additionally, Diclofenac sodium has been shown to induce apoptosis in neural stem cells through the activation of the caspase cascade, making it a valuable tool in biochemical and pharmacological research.

Mitotane-13C6 is a stable isotope-labeled form of Mitotane (2,4′-DDD), which targets adrenocortical carcinoma. This antineoplastic agent exerts its effects primarily through lipotoxicity resulting from the accumulation of intracellular free cholesterol. Additionally, Mitotane influences pituitary function by affecting corticotroph cells and induces CYP3A4 gene expression via activation of the steroid and xenobiotic receptor (SXR). This compound is essential for studies investigating adrenocortical function and drug interactions.

L-Asparagine-13C4,15N2,d8 is a stable isotope-labeled form of the amino acid L-Asparagine, enriched with carbon-13 and nitrogen-15 isotopes. This compound plays a critical role in cancer research, particularly in the study of leukemia, as it serves as a substrate for the enzyme L-Asparaginase, which depletes asparagine and glutamine levels in the body. By inhibiting RNA and DNA synthesis in lymphoblasts, L-Asparaginase induces apoptosis in leukemic cells, making L-Asparagine-13C4,15N2,d8 a valuable tool for understanding mechanisms of cancer cell growth and for investigating childhood acute lymphoblastic leukemia.

5-Aminolevulinic acid-13C-1 hydrochloride is a stable isotope-labeled form of 5-aminolevulinic acid, an essential intermediate in heme biosynthesis and a universal precursor of tetrapyrroles. This compound is widely utilized in metabolic research and tracer studies to investigate the dynamics of heme synthesis and its regulatory mechanisms. The incorporation of the 13C label enables advanced analytical techniques for tracking metabolic pathways and studying the role of heme-related compounds in various biological processes.

Flubendazole-d3 is a deuterium-labeled derivative of Flubendazole, a well-established anthelmintic agent targeting microtubule function. This compound exhibits significant biological activity, including the induction of p53-mediated apoptosis and the arrest of the G2/M cell cycle phase. Flubendazole-d3 is useful in research applications focused on antiparasitic therapies and cancer treatment mechanisms, providing a stable isotope variant for advanced analytical studies.

Tamoxifen-d3 is a deuterium-labeled derivative of Tamoxifen, a selective estrogen receptor modulator (SERM) that primarily functions by inhibiting estrogen action in breast tissue while potentially activating it in other tissues such as bone, liver, and uterus. This compound serves as a powerful Hsp90 activator, enhancing ATPase activity, and exhibits inhibition of EBOV Zaire and Marburg viruses with IC50 values of 0.1 μM and 1.8 μM, respectively. Tamoxifen-d3 is used in various research applications including studies on autophagy, apoptosis induction, and gene knockout in CreER(T2) transgenic models.

Glyphosate-13C is a stable isotope-labeled form of glyphosate, a non-selective systemic herbicide that targets the 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS) within the shikimic acid pathway. By inhibiting EPSPS, glyphosate effectively disrupts the synthesis of key aromatic amino acids, including tyrosine, phenylalanine, and tryptophan. Its biological activity includes the induction of oxidative stress and neuroinflammation, which can lead to mitochondrial dysfunction and neuronal cell death through autophagy or apoptosis. This compound is useful in research applications related to herbicide metabolism, environmental impact studies, and understanding the neurotoxic effects associated with glyphosate exposure.

Perphenazine-d4 is a deuterated derivative of Perphenazine, a typical antipsychotic agent primarily inhibiting the 5-HT2A receptor, alpha-1A adrenergic receptor, dopamine receptor D2/D3, D2L receptor, and histamine H1 receptor, with Ki values of 5.6, 10, 0.765/0.13, 3.4, and 8 nM, respectively. This stable isotope is valuable for pharmacokinetic studies, allowing for the precise tracking of Perphenazine metabolism and distribution in biological systems. Perphenazine-d4 is essential for researchers focusing on neuropharmacology and drug interaction studies involving antipsychotic medications.

5-Fluorouracil-13C,15N2 is a stable isotope-labeled derivative of 5-Fluorouracil (5-FU), an analogue of uracil known for its potent antitumor activity. It primarily targets thymidylate synthetase, leading to a significant reduction in intracellular dTTP levels, thereby disrupting pyrimidine synthesis and promoting apoptosis. This compound is valuable in cancer research and may also provide insights into mechanisms of viral inhibition, including activity against HIV.

Thiocolchicine-d3 is a deuterium-labeled derivative of Thiocolchicine, which acts as a potent inhibitor of tubulin polymerization. With an IC50 of 2.5 μM, it competitively binds to tubulin, exhibiting a Ki of 0.7 μM. This compound is known to induce apoptosis in cells and can serve as a cytotoxic agent in antibody-drug conjugate (ADC) applications, making it valuable for cancer research and therapeutic development.

Meloxicam-13C,d3 is a deuterated derivative of Meloxicam, a non-steroidal anti-inflammatory drug that inhibits cyclooxygenase (COX) enzyme activity, exhibiting IC50 values of 0.49 µM for COX-2 and 36.6 µM for COX-1. This stable isotope-labeled compound is primarily utilized in pharmacokinetic studies and metabolism research, enabling precise tracking and quantification in biological systems. Its application enhances the understanding of Meloxicam's pharmacological properties and interactions within various biological contexts.

Salicylic acid-13C6 is a stable isotope-labeled form of salicylic acid, a key metabolite and precursor of aspirin. This compound functions primarily as a cyclo-oxygenase-2 (COX-2) inhibitor, making it relevant for studies focused on inflammation and pain management. Salicylic acid-13C6 is widely used in metabolomics and tracer studies to investigate metabolic pathways and the pharmacokinetics of aspirin and its derivatives.

2,4-D-13C6 is a stable isotope-labeled form of 2,4-Dichlorophenoxyacetic acid (2,4-D), a selective systemic herbicide. This compound functions as a plant growth regulator by mimicking natural hormones, leading to uncontrolled growth in meristematic tissues. 2,4-D-13C6 is utilized in research applications involving herbicide behavior, plant physiology studies, and tracking metabolic pathways in plants. Its stable isotope label facilitates precise quantification and tracing in complex biological systems.

β-Zearalanol-d4 is a deuterated derivative of β-Zearalenol, representing a stable isotope for precision studies. As a mycotoxin produced by Fusarium species, β-Zearalenol induces apoptosis and oxidative stress in mammalian reproductive cells, making it pertinent for research into reproductive toxicity. This compound is instrumental for investigations involving zearalenone (ZEA) and its metabolic pathways, including conjugation with glucuronic acid.

Metronidazole-d4 is a deuterium-labeled derivative of Metronidazole, a nitroimidazole antibiotic that selectively targets anaerobic bacteria and protozoa. This stable isotope is ideal for use in pharmacokinetic studies and metabolic research, allowing for precise tracking and quantification of drug metabolism and efficacy. Its application extends to elucidating metabolic pathways and assessing drug interactions in various biological systems.

Apocynin-d3 is a deuterium-labeled analog of Apocynin, specifically designed for use as a stable isotope in research applications. As a selective inhibitor of NADPH oxidase, it exhibits an IC50 value of 10 μM, making it a valuable tool for investigating oxidative stress and associated signaling pathways. This compound is particularly useful in studies of inflammatory processes and cardiovascular diseases, facilitating the elucidation of NADPH oxidase's role in various biological systems.

1-Stearoyl-sn-glycero-3-phosphocholine-d35 is a deuterium-labeled variant of 1-Stearoyl-sn-glycero-3-phosphocholine, serving as a stable isotope for precision research applications. This lysophosphatidylcholine inhibits histone deacetylase 3 (HDAC3) activity and reduces phosphorylation of STAT3 in K562 cells. Additionally, it induces apoptosis and demonstrates anticancer properties specifically in chronic myelogenous leukemia (CML) K562 cells, making it valuable for studies in cancer biology and therapeutic development.

2,4-Di-tert-butylphenol-d21 is a deuterated form of 2,4-Di-tert-butylphenol, serving as a stable isotope for research applications. This compound exhibits significant biological activity as an RXRα activator and a ligand for the human estrogen receptor, demonstrating anti-inflammatory and antioxidant properties. Additionally, it can induce apoptosis in tumor cells and activate RXRα in various receptor complexes. Its diverse applications include studying neurotoxicity, as well as serving as an intermediate in the development of antioxidants, UV stabilizers, and pharmaceuticals.

L-Ascorbic acid-13C-2 is a stable isotope-labeled form of L-Ascorbic acid, serving as an electron donor and a potent endogenous antioxidant. This compound is known for its selective inhibition of Cav3.2 channels, exhibiting an IC50 of 6.5 μM. L-Ascorbic acid's role in collagen synthesis further highlights its importance in various biological research applications, making it invaluable for studies related to antioxidant activity and cellular physiology.

L-Asparagine-amide-15N monohydrate is a stable isotope-labeled form of the amino acid L-Asparagine. It serves as an essential substrate for L-Asparaginase, an enzyme that depletes asparagine and glutamine levels, ultimately inhibiting protein biosynthesis in leukemic cells. This compound is instrumental in research applications targeting childhood acute lymphoblastic leukemia, where the depletion of asparagine leads to inhibited RNA and DNA synthesis, promoting apoptosis in cancer cells with low asparagine synthetase expression. Additionally, L-Asparagine monohydrate functions as a valuable biomarker and sensor in studies of leukemic cell metabolism.

Maltol-d3 is a deuterated form of Maltol, functioning as a stable isotope. Maltol exhibits significant antioxidant properties, promoting neural health by reducing oxidative stress and preventing apoptosis. This compound is particularly useful in research focused on neuroprotection, including studies on diabetic peripheral neuropathy. Additionally, Maltol acts as a chelator for metal ions, making it applicable in various fields, including catalysis, cosmetics, and medicinal research.

Nitrendipine-d5 is a deuterium-labeled analog of Nitrendipine, a dihydropyridine calcium channel blocker. This compound exhibits significant antihypertensive effects and promotes apoptosis in various cell types. Nitrendipine has been shown to alleviate withdrawal symptoms associated with alcohol and morphine and can mitigate right ventricular hypertrophy and pulmonary vascular alterations due to intermittent hypoxia. Additionally, Nitrendipine demonstrates anticancer activities, particularly against neuroblastoma, making it a valuable tool for research in cardiovascular and cancer biology.

Orlistat-d3 is a deuterated form of Orlistat, a well-characterized irreversible inhibitor of pancreatic and gastric lipases. This compound also inhibits fatty acid synthase (FASN) and serves as a vital tool for studying obesity and metabolic disorders. Its applications extend to research on anti-atherosclerotic effects and long-term dietary interventions.

Ibuprofen-13C6 is a stable isotope-labeled form of ibuprofen, a potent and selective inhibitor of cyclooxygenase-1 (COX-1) with an IC50 value of 13 μM. This compound exhibits key biological activities including the inhibition of cell proliferation, angiogenesis, and the induction of apoptosis. As a nonsteroidal anti-inflammatory drug (NSAID) and nitric oxide (NO) donor, Ibuprofen-13C6 serves as an important reagent in research related to pain, inflammation, immunology, and cancer biology.

Sunitinib-d10 is a deuterium-labeled variant of Sunitinib, a multi-targeted receptor tyrosine kinase inhibitor that primarily targets VEGFR2 and PDGFRβ with IC50 values of 80 nM and 2 nM, respectively. As an ATP-competitive inhibitor, Sunitinib-d10 effectively blocks autophosphorylation of Ire1α, thereby inhibiting its RNase activity. This stable isotope is utilized in pharmacokinetic studies and metabolic labeling, facilitating deeper insights into kinase signaling pathways and drug metabolism.

Cytarabine-d2 is a deuterium-labeled analog of Cytarabine, targeting DNA synthesis inhibition. As a nucleoside analog, it induces S phase cell cycle arrest and effectively inhibits DNA polymerase activity, exhibiting an IC50 of 16 nM. In addition to its role in cancer research, Cytarabine-d2 displays antiviral properties against herpes simplex virus (HSV), making it pertinent for studies in virology and oncology.

Adenosine-13C is a stable isotope-labeled form of adenosine, a naturally occurring purine nucleoside that interacts with various G protein-coupled receptors, including A1, A2A, A2B, and A3. This compound plays a critical role in numerous biological processes, including modulation of neurotransmission, immune responses, and cardiovascular function. Adenosine-13C serves as an essential tool in metabolic and pharmacological research, facilitating studies related to receptor signaling and metabolic pathways in various cellular contexts.

Idebenone-13C,d3 is a deuterium and carbon-13 labeled derivative of Idebenone, a potent mitochondrial protectant. It demonstrates neuroprotective effects and is relevant for studying neurodegenerative disorders such as Alzheimer's disease and Huntington's disease. Idebenone exhibits a dose-dependent inhibitory effect on the enzymatic metabolism of arachidonic acid, with an IC50 of 16.65 μM, and induces apoptotic cell death in SHSY-5Y human dopaminergic neuroblastoma cells. Additionally, it readily penetrates the blood-brain barrier, enhancing its potential in neurological research.

Dihexyl phthalate-3,4,5,6-d4 is a deuterium-labeled derivative of Dihexyl phthalate, a noted phthalate ester prevalent in plastics and consumer products. This compound serves as a stable isotope tracer for environmental studies, particularly in assessing the fate and transport of phthalates in ecosystems. Dihexyl phthalate is recognized for its role as an endocrine disruptor, promoting the accumulation of reactive oxygen species, inflammation, and increased apoptosis. It is considered a reproductive toxicant and has been linked to testicular atrophy, making it significant for research in toxicology and reproductive health.

Sodium propionate-d3 is a deuterium-labeled form of sodium propionate, a short-chain fatty acid that functions as a stable isotope. It selectively enhances PPAR-γ activation while inhibiting NF-κB activation, reducing COX-2 expression and nitric oxide production. This compound exhibits significant biological activities, including apoptosis induction and autophagy promotion, along with neuroprotective, antioxidant, and anti-inflammatory properties. Sodium propionate-d3 is valuable in research applications related to spinal cord injury, Alzheimer's disease, and the treatment of glioblastoma, as well as in studying viral infections such as HSV-1-induced keratitis.

Risedronic acid-d4 is a deuterium-labeled derivative of Risedronic acid, a bisphosphonate known for its potent antiresorptive effects. This compound functions primarily by inhibiting osteoclast-mediated bone resorption and altering bone metabolism, making it essential for studies related to osteoporosis and related conditions. In addition, Risedronic acid has been shown to induce apoptosis and inhibit the transfer of farnesyl pyrophosphate groups in parasites, with notable activity against the blood-stage of Plasmodium falciparum (IC50 of 20.3 μM). Risedronic acid-d4 serves as a valuable tool in chemical research and metabolic studies.

Laquinimod-d5 is a deuterium-labeled variant of Laquinimod, a potent immunomodulator primarily targeting neuroinflammation in the central nervous system. This compound effectively reduces astrocytic NF-κB activation, offering protection against demyelination induced by Cuprizone. Laquinimod-d5 is intended for research applications exploring relapsing-remitting and chronic progressive forms of multiple sclerosis, as well as various neurodegenerative diseases.