| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
11-Mercaptoundecanoic acid does not have a biological drug target; its "targets" are solid surfaces (gold, silver, platinum) and chemical reagents. The thiol group forms a strong covalent bond with gold surfaces (Au-S bond), creating a highly ordered SAM. The exposed carboxylic acid group can be activated (e.g., with EDC/NHS) to covalently immobilize proteins, antibodies, DNA probes, or other ligands. This allows the construction of molecular recognition interfaces for biosensing, drug delivery, and tissue engineering applications.
|
|---|---|
| ln Vitro |
The in vitro activity of 11-Mercaptoundecanoic acid is not defined in terms of biological modulation but rather in surface chemistry. Its ability to form SAMs is characterized by contact angle measurements (increasing hydrophobicity after SAM formation), ellipsometry (film thickness of ~1.5-2 nm), and electrochemical methods (blocking of electron transfer by the insulating alkyl chain). The exposed carboxylic acid groups can be quantified by colorimetric assays (e.g., Toluidine Blue O staining) or by fluorescence labeling with amine-reactive dyes. These assays confirm the functional density of the SAM.
|
| ln Vivo |
In vivo activity of 11-Mercaptoundecanoic acid as a free molecule is not relevant because it is not administered as a drug. However, gold nanoparticles coated with this compound (via thiol linkage) have been investigated in vivo for drug delivery and imaging. For example, PEGylated gold nanoparticles bearing carboxylic acid groups from this compound can be conjugated to tumor-targeting antibodies. After intravenous injection into tumor-bearing mice, these nanoparticles accumulate in tumors via enhanced permeability and retention (EPR) effect and show prolonged circulation due to reduced protein adsorption (the COOH group can be further modified to reduce opsonization).
|
| Enzyme Assay |
An in vitro non-cellular assay for 11-Mercaptoundecanoic acid is the formation of a self-assembled monolayer on a gold-coated quartz crystal microbalance (QCM) sensor. A 1 mM solution of the compound in ethanol is flowed over the gold-coated QCM chip. The frequency decrease is monitored in real-time, and the mass of adsorbed monolayer is calculated using the Sauerbrey equation. The thickness of the SAM can also be measured by ellipsometry. For chemical reactivity, the carboxylic acid groups are activated by 0.1 M EDC/0.025 M NHS in MES buffer at pH 5.5, and coupling efficiency with amine-containing molecules is assessed by UV-Vis or by using labeled streptavidin.
|
| Cell Assay |
11-Mercaptoundecanoic acid is not used directly on cells because the free thiol can reduce disulfide bonds in cell surface proteins and cause cytotoxicity. However, after immobilization on gold nanoparticles or planar surfaces, the compound's conjugates can be tested in cell assays. For instance, gold nanoparticles functionalized with 11-Mercaptoundecanoic acid and conjugated to an anti-HER2 antibody are added to HER2-positive SK-BR-3 breast cancer cells. After 4-24 hours, cell uptake is visualized by dark-field microscopy or quantified by ICP-MS measuring gold content. Cell viability is assessed by MTT to evaluate the nanoparticle's biocompatibility.
|
| Animal Protocol |
In vivo experiments involving this compound are conducted with its surface-functionalized nanoparticles. For example, BALB/c nude mice bearing SK-BR-3 xenografts are injected intravenously with 11-Mercaptoundecanoic acid-coated gold nanoparticles conjugated to a targeting ligand. Blood samples are collected at 0, 1, 4, 8, 24, and 48 h to measure gold concentration by ICP-MS. Mice are euthanized at 24 h or 48 h, and organs (liver, spleen, kidney, tumor) are harvested for gold quantification. Biodistribution profiles show predominant accumulation in liver and spleen, with some tumor uptake depending on targeting efficiency.
|
| ADME/Pharmacokinetics |
The pharmacokinetic properties of free 11-Mercaptoundecanoic acid are not characterized as it is not a therapeutic. However, when used as a coating for nanoparticles, the pharmacokinetics of the nanoparticles are influenced by the surface charge and hydrophilicity. The carboxylic acid-terminated SAM confers a negative surface charge (zeta potential ~ -30 to -40 mV at pH 7.4), which can reduce non-specific protein adsorption and prolong circulation half-life compared to positively charged coatings. Typical half-life of such nanoparticles in mice is 2-6 hours, with clearance primarily by the liver and spleen. The compound itself is metabolized via beta-oxidation of the alkyl chain.
|
| Toxicity/Toxicokinetics |
11-Mercaptoundecanoic acid is considered moderately toxic. The thiol group can cause skin and eye irritation (H315, H319). Inhalation of dust may irritate respiratory tract. The LD50 in rats is not well reported, but structurally similar mercaptoalkanoic acids have oral LD50 around 500-1000 mg/kg. Chronic exposure may cause kidney and liver damage. Environmental toxicity: harmful to aquatic life. Standard precautions: use fume hood, wear nitrile gloves, safety goggles. Store at 2-8degC under inert gas (to prevent disulfide formation). In case of skin contact, wash thoroughly with soap and water.
|
| References | |
| Additional Infomation |
11-Mercaptoundecanoic acid (CAS 71310-21-9) has molecular formula C11H22O2S and molecular weight 218.36 g/mol. Melting point 43-47degC. Solubility: soluble in ethanol, DMSO, and alkaline aqueous solutions (as carboxylate salt); poorly soluble in pure water. It is a key reagent in the fabrication of electrochemical biosensors (e.g., glucose sensors, DNA chips), in the preparation of thiolated polymers for drug delivery, and in the creation of stimuli-responsive surfaces. This compound is not a pharmaceutical and has no FDA approval or clinical trials.
|
| Molecular Formula |
C11H22O2S
|
|---|---|
| Molecular Weight |
218.36
|
| Exact Mass |
218.134
|
| CAS # |
71310-21-9
|
| PubChem CID |
543502
|
| Appearance |
Solid powder
|
| Density |
0.998g/cm3
|
| Boiling Point |
352.209ºC at 760 mmHg
|
| Melting Point |
46-50ºC(lit.)
|
| Flash Point |
110ºC
|
| Index of Refraction |
1.483
|
| LogP |
3.511
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
10
|
| Heavy Atom Count |
14
|
| Complexity |
137
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
S([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(=O)O[H]
|
| InChi Key |
GWOLZNVIRIHJHB-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C11H22O2S/c12-11(13)9-7-5-3-1-2-4-6-8-10-14/h14H,1-10H2,(H,12,13)
|
| Chemical Name |
11-sulfanylundecanoic acid
|
| Synonyms |
11-Thioundecanoic acid; MUA; MUDA; 11-Mercaptoundecanoic acid
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO : 200 mg/mL (915.92 mM; with sonication)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.45 mM)(Saturation unknown) in 10% DMSO 40% PEG300 5% Tween-80 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, add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix well; then add 50 μL Tween-80 to the above system and mix well; then add 450 μL saline to make up 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 (11.45 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, add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD in saline and mix well. *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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.5796 mL | 22.8980 mL | 45.7959 mL | |
| 5 mM | 0.9159 mL | 4.5796 mL | 9.1592 mL | |
| 10 mM | 0.4580 mL | 2.2898 mL | 4.5796 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
