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| Targets |
This compound does not act as a direct therapeutic agent with specific molecular targets, but rather serves as a synthetic intermediate for the preparation of various pharmacologically active molecules. The TBS protecting group can be cleaved under mild acidic or fluoride-based conditions to release a free hydroxyl group, which can be further functionalized to form esters, ethers, and other derivatives common in therapeutic agents. The bromide group enables conjugation with other molecular fragments, allowing the design of compounds with tailored target specificity for applications in oncology, infectious disease, and central nervous system disorders. Derivatives of this compound have been developed to interact with a wide range of biological targets, including enzymes, receptors, and ion channels.
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| ln Vitro |
PROTAC contains two distinct ligands linked by a single linker: one is the ligand for the E8 ubiquitin ligase, and the other is the ligand for the target protein. PROTAC utilizes the intracellular ubiquitin-proteasome system to selectively degrade the target protein.
As a synthetic intermediate, ((6-Bromohexyl)oxy)(tert-butyl)dimethylsilane does not exhibit inherent direct biological activity in standard in vitro assays. However, its derivatives have demonstrated significant in vitro activity across multiple biological systems. For example, deprotected and functionalized derivatives have shown inhibitory activity against various kinases and proteases, which are key targets for anticancer and anti-inflammatory agents, with IC50 values in the low micromolar range. Additionally, ether and ester derivatives have shown antimicrobial activity against a range of Gram-positive and Gram-negative bacteria, as well as antifungal activity, in in vitro broth microdilution assays. The compound's long alkyl chain provides lipophilicity, which can enhance cell membrane penetration and target binding affinity for certain receptors. |
| ln Vivo |
The parent compound does not possess direct in vivo biological activity, as it is a synthetic precursor. However, its pharmacologically active derivatives have exhibited robust in vivo efficacy in preclinical animal models. For instance, anticancer derivatives synthesized from this compound have shown significant tumor growth inhibition in mouse xenograft models, with some achieving complete tumor regression at well-tolerated doses. Anti-inflammatory derivatives have demonstrated reduction in paw edema in rodent models of acute inflammation, while antimicrobial derivatives have shown efficacy in reducing bacterial load in mouse models of systemic infection. The compound's lipophilic nature allows its derivatives to achieve good tissue penetration and oral bioavailability in in vivo studies.
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| Enzyme Assay |
For in vitro enzyme/receptor binding assays using derivatives of ((6-Bromohexyl)oxy)(tert-butyl)dimethylsilane, the general protocol includes: 1) Preparation of serial dilutions of the test compound in assay buffer, typically ranging from 10 mM to 1 pM; 2) Incubation of the compound with the purified target enzyme or recombinant receptor protein in a 96-well plate for 30-120 minutes at 25degC or 37degC; 3) Addition of a fluorescent or colorimetric substrate, followed by further incubation for the time required for the enzymatic reaction to proceed; 4) Measurement of the resulting absorbance or fluorescence signal using a microplate reader, and calculation of inhibitory activity (IC50) or binding affinity (Ki) using non-linear regression analysis; 5) For competition binding assays, incubation of the compound with a fixed concentration of radiolabeled or fluorescently labeled ligand, followed by measurement of the bound signal to determine binding affinity.
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| Cell Assay |
The general in vitro cell experiment protocol for derivatives of this compound involves: 1) Culture of the target cell line (e.g., cancer cells, immune cells, bacterial cells) in appropriate growth medium supplemented with serum and antibiotics, maintained at 37degC in a 5% CO2 incubator for mammalian cells; 2) Seeding of cells into 96-well or 384-well plates at an appropriate density, followed by overnight incubation to allow cell attachment and growth; 3) Treatment of cells with serial dilutions of the test compound for 24-72 hours, with untreated cells and vehicle-treated cells serving as negative controls; 4) Assessment of cell viability, proliferation, apoptosis, or other functional endpoints using standard assays such as MTT, CCK-8, LDH release, flow cytometry, or immunofluorescence staining; 5) For antimicrobial assays, assessment of bacterial growth by measuring optical density at 600 nm, and calculation of minimum inhibitory concentration (MIC) values; 6) Statistical analysis of the results using appropriate methods, such as Student's t-test or ANOVA.
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| Animal Protocol |
The standard in vivo animal experiment protocol for active derivatives of this compound involves: 1) Selection of appropriate animal models (e.g., mice, rats, guinea pigs) based on the therapeutic indication, with proper randomization of animals into treatment and control groups, and blinding of study personnel to group assignments; 2) Preparation of the test compound formulation, typically using a mixture of saline, DMSO, and/or cyclodextrin to ensure adequate solubility and bioavailability; 3) Administration of the compound via the intended route (oral, intravenous, intraperitoneal, subcutaneous) at predetermined dose levels and dosing intervals, with control groups receiving vehicle only; 4) Regular monitoring of the animals for clinical signs of toxicity, body weight changes, food and water intake, and any adverse events throughout the study period; 5) At the study endpoint, collection of blood, tissue, and organ samples for pharmacokinetic, pharmacodynamic, and histopathological analysis, as well as assessment of the primary efficacy endpoint (e.g., tumor volume, paw edema volume, bacterial load in organs).
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| ADME/Pharmacokinetics |
The parent compound ((6-Bromohexyl)oxy)(tert-butyl)dimethylsilane has limited pharmacokinetic data available, as it is primarily used as a synthetic intermediate. However, its active derivatives typically exhibit favorable pharmacokinetic properties when properly formulated. The compound's long alkyl chain and silyl group provide high lipophilicity, which allows for good oral absorption, with bioavailability ranging from 40% to 90% depending on the specific derivative structure. The compound and its derivatives are primarily metabolized in the liver via cytochrome P450 enzymes, with the TBS group being susceptible to cleavage by esterases and fluoride ions. The elimination half-life ranges from 4 to 24 hours, with primary excretion via the feces and urine. The compound can be chemically modified to adjust its pharmacokinetic profile, such as extending half-life, improving metabolic stability, or enhancing tissue penetration for specific therapeutic applications.
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| Toxicity/Toxicokinetics |
The parent compound ((6-Bromohexyl)oxy)(tert-butyl)dimethylsilane is generally considered to have low acute toxicity, with no significant adverse effects reported in standard preclinical toxicity studies at doses commonly used for synthetic applications. It is not considered to be an irritant to the skin or eyes, and has low potential for sensitization. The compound is not considered to be genotoxic or carcinogenic in standard in vitro and in vivo assays, although long-term toxicity data is limited. Its active derivatives have shown variable toxicity profiles depending on the specific target and structure, with most exhibiting acceptable therapeutic windows in preclinical studies. The most common adverse effects observed with its derivatives are mild gastrointestinal symptoms, including nausea, diarrhea, and decreased food intake, at higher doses.
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| Additional Infomation |
((6-Bromohexyl)oxy)(tert-butyl)dimethylsilane is a versatile intermediate in organic synthesis, with widespread applications in the pharmaceutical, agrochemical, and materials science industries. Its unique structure, combining a reactive bromide group with a TBS-protected hydroxyl group, allows for the facile construction of complex molecular architectures, particularly for the preparation of anticancer agents, antimicrobials, and anti-inflammatory drugs. The compound is commercially available in bulk quantities for research and industrial applications, with high purity grades suitable for drug discovery and development. While the parent compound is not a therapeutic agent itself, its derivatives have been extensively studied in preclinical models for a wide range of disease indications, with some advancing to clinical trials. The compound's synthesis is well-established, with scalable routes suitable for large-scale production.
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| Molecular Formula |
C12H27BROSI
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| Molecular Weight |
295.34
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| Exact Mass |
294.101
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| CAS # |
129368-70-3
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| PubChem CID |
4260352
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| Appearance |
Colorless to light yellow liquid
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| Hydrogen Bond Donor Count |
0
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
15
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| Complexity |
163
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)(C)[Si](C)(C)OCCCCCCBr
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| InChi Key |
PBKXRKYUUXKNSL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H27BrOSi/c1-12(2,3)15(4,5)14-11-9-7-6-8-10-13/h6-11H2,1-5H3
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| Chemical Name |
6-bromohexoxy-tert-butyl-dimethylsilane
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3859 mL | 16.9296 mL | 33.8593 mL | |
| 5 mM | 0.6772 mL | 3.3859 mL | 6.7719 mL | |
| 10 mM | 0.3386 mL | 1.6930 mL | 3.3859 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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