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| Targets |
3-Chlorogentisyl alcohol targets multiple biological systems and enzymes. It is a potent inhibitor of E. coli beta-glucuronidase, a bacterial enzyme that can reactivate glucuronidated drug metabolites in the intestine, contributing to drug-induced gastrointestinal toxicity. The compound has an IC50 of 0.74 microM and a Ki of 0.58 microM for E. coli beta-glucuronidase. It also exhibits antioxidant activity by scavenging DPPH radicals (IC50 = 1 uM), antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA) and other Gram-positive bacteria, and antiproliferative activity against cancer cells.
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| ln Vitro |
3-Chlorogentisyl alcohol (Compound 1) (20 µM; 24 hours) antiproliferative action in Namalwa, U266 cells [1].
In vitro, 3-Chlorogentisyl alcohol potently inhibits E. coli beta-glucuronidase with an IC50 of 0.74 microM and a Ki of 0.58 microM, demonstrating strong binding affinity. It acts as a DPPH radical scavenger with an IC50 of 1 microM, confirming its antioxidant capacity. In antimicrobial assays, it is active against methicillin-resistant S. aureus (MRSA) with an MIC of 50 ug/mL, as well as against 13 other Gram-positive and Gram-negative bacteria at a concentration of 200 ug/mL. It also exhibits antiproliferative activity against cancer cell lines, suggesting potential for anti-cancer and anti-inflammatory research. |
| ln Vivo |
In vivo, 3-Chlorogentisyl alcohol has not been extensively studied, but it is of interest for its potential to inhibit E. coli beta-glucuronidase in the gut. By inhibiting this bacterial enzyme, the compound could reduce the reactivation of certain glucuronidated drug metabolites (e.g., irinotecan or NSAIDs) in the intestine, thereby alleviating drug-induced gastrointestinal side effects such as diarrhea. This mechanism has been explored as a therapeutic strategy to improve the tolerability of certain anticancer drugs. However, detailed in vivo efficacy data in animal models is limited.
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| Enzyme Assay |
For non-cell-based enzyme inhibition assays, a standard protocol is used for beta-glucuronidase inhibition. E. coli beta-glucuronidase is diluted in assay buffer (100 mM sodium phosphate, pH 7.4, 1 mM EDTA, 10% DMSO) to a final concentration of 0.1 U/mL. The reaction mixture (total volume 200 uL) contains enzyme, varying concentrations of 3-Chlorogentisyl alcohol (0.01-1000 uM), and the fluorogenic substrate 4-methylumbelliferyl-beta-D-glucuronide (4-MUG, 200 uM). The reaction is initiated by addition of substrate and incubated at 37degC for 30 min. The reaction is terminated by adding 1 M sodium carbonate (50 uL). Fluorescence is measured at Ex 365 nm/Em 445 nm. The IC50 is calculated from the dose-response curve, and the Ki is determined by performing the assay at multiple substrate concentrations (Lineweaver-Burk analysis). For DPPH radical scavenging assays, 3-Chlorogentisyl alcohol at varying concentrations (0.1-100 uM) is mixed with DPPH (100 uM) in ethanol. After incubation at room temperature for 30 min in the dark, the decrease in absorbance at 517 nm is measured, and the IC50 for DPPH scavenging is calculated.
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| Cell Assay |
Cell proliferation assay [1]
Cell Types: Namalwa, U266 Cell Tested Concentrations: 20 µM Incubation Duration: 24 h Experimental Results: It has anti-proliferative activity, and the survival rates of Namalwa and U266 cells were 70.40% and 94.08% respectively. For in vitro cell-based assays, human cancer cell lines (e.g., HeLa, MCF-7, or A549) are seeded in 96-well plates at 5 × 10^3 cells/well and cultured for 24 hours. Cells are then treated with varying concentrations of 3-Chlorogentisyl alcohol (0-200 uM) for 48-72 hours. Cell viability is measured by MTT assay (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide). For antimicrobial assays, bacterial strains (e.g., MRSA ATCC 43300, E. coli) are cultured overnight in Mueller-Hinton broth. The minimum inhibitory concentration (MIC) is determined by the broth microdilution method in 96-well plates. Bacterial suspensions (5 × 10^5 CFU/mL) are added to wells containing serial twofold dilutions of the compound (6.25-400 ug/mL). Plates are incubated at 37degC for 18-20 hours, and the MIC is defined as the lowest concentration inhibiting visible bacterial growth. |
| Animal Protocol |
Detailed in vivo protocols for this compound are limited, as it remains a research-grade compound. However, a mouse model of irinotecan-induced gastrointestinal toxicity could be used to evaluate the in vivo efficacy of 3-Chlorogentisyl alcohol as an E. coli beta-glucuronidase inhibitor. Female BALB/c mice (6-8 weeks old) are treated with irinotecan (50 mg/kg, IP) to induce diarrhea. 3-Chlorogentisyl alcohol is administered orally (10-50 mg/kg) twice daily for 3-7 days. Control groups receive vehicle (e.g., 0.5% methylcellulose) or a positive control inhibitor (e.g., amoxapine). Mice are monitored for diarrhea severity (scoring system: 0=normal, 1=mild, 2=moderate, 3=severe, 4=lethal), body weight loss, and survival. At study endpoint (day 7), cecal contents are collected for measurement of beta-glucuronidase activity and quantification of bacterial abundance. Plasma is collected for measurement of drug exposure (irinotecan and SN-38). The compound is not a clinical drug.
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| ADME/Pharmacokinetics |
3-Chlorogentisyl alcohol has a molecular weight of 174.58 g/mol and a molecular formula of C7H7ClO3. The compound is sparingly soluble in water and soluble in organic solvents such as DMSO, ethanol, and PBS (pH 7.2) at 1-10 mg/mL. For in vivo studies, the compound is typically formulated in DMSO/PEG400/saline or 0.5% methylcellulose for oral administration. Pharmacokinetic data is not available, but as a small phenolic compound, it is expected to have good oral absorption, rapid distribution, and conjugation (glucuronidation/sulfation) as the primary metabolic pathways. The half-life in rodents is likely 1-2 hours.
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| Toxicity/Toxicokinetics |
Specific toxicity data for 3-Chlorogentisyl alcohol is not publicly available. As a naturally occurring microbial metabolite and a chlorinated phenolic compound, it is generally considered to have low to moderate toxicity. At the concentrations used for beta-glucuronidase inhibition in cell-free assays (IC50 0.74 uM) and antimicrobial assays (MIC 50 ug/mL), the compound is not expected to cause significant mammalian cell toxicity. In cell viability assays, the compound may exhibit an IC50 for antiproliferative activity in the range of 20-100 uM, indicating a therapeutic window. Standard safety precautions (gloves, lab coat, eye protection) should be used when handling the compound.
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| References | |
| Additional Infomation |
Chloroisothiocyanates are organohalides belonging to the hydroquinone class of compounds. 3-Chloroisothiocyanates have been reported to exist in Penicillium terrestris, Penicillium monotyphi, and other organisms with relevant data.
3-Chlorogentisyl alcohol is a research compound and is not approved for clinical use. It is a chlorinated hydroquinone derivative with a 2-chloro-6-(hydroxymethyl)benzene-1,4-diol structure. Gentisyl alcohol (2,5-dihydroxybenzyl alcohol) is known to be produced by various fungi, and its 3-chloro derivative is a halogenated analog with enhanced bioactivity. The compound has been isolated from endophytic fungi such as Ampelomyces and is investigated for its potential as a beta-glucuronidase inhibitor to reduce drug-induced gastrointestinal toxicity. This compound is also of interest for its antioxidant and antimicrobial properties, with potential applications in the food and cosmetic industries. It is for research use only. |
| Molecular Formula |
C7H7O3CL
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|---|---|
| Molecular Weight |
174.58168
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| Exact Mass |
174.008
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| CAS # |
32744-80-2
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| PubChem CID |
593615
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| Appearance |
Off-white to light yellow solid powder
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| LogP |
1.327
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
131
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| Defined Atom Stereocenter Count |
0
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| SMILES |
OCc1cc(O)cc(Cl)c1O
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| InChi Key |
GUIGFYWMQAYTBT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H7ClO3/c8-6-2-5(10)1-4(3-9)7(6)11/h1-2,9-11H,3H2
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| Chemical Name |
2-chloro-6-(hydroxymethyl)benzene-1,4-diol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~572.80 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.32 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (14.32 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (14.32 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.7280 mL | 28.6402 mL | 57.2803 mL | |
| 5 mM | 1.1456 mL | 5.7280 mL | 11.4561 mL | |
| 10 mM | 0.5728 mL | 2.8640 mL | 5.7280 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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