| Size | Price | Stock | Qty |
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| 50g |
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| 100g |
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| 500g |
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| Other Sizes |
| Targets |
This compound has weak biological activity. L-Tartaric acid derivatives are known to inhibit certain enzymes such as tartrate-resistant acid phosphatase (TRAP) and some matrix metalloproteinases (MMPs). The (2S,3S) stereochemistry is important for binding. It can chelate metal ions (e.g., Fe3+, Ca2+) due to the diol and carboxylate groups. The methyl esters are prodrugs.
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| ln Vitro |
PROTAC contains two distinct ligands linked by a single linker: one is the ligand for the E12 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.
In vitro, the free acid (tartaric acid) inhibits TRAP with IC50 ~100 uM. The dimethyl ester is less active. As a building block, it can be incorporated into HIV protease inhibitors (e.g., amprenavir analogs) with IC50 in the low nM range. The compound itself is not potently active against cancer cells (IC50 >1 mM). |
| ln Vivo |
No direct in vivo activity. A HIV protease inhibitor synthesized from this scaffold (e.g., amprenavir) has in vivo efficacy (viral load reduction) at 10 mg/kg PO. The dimethyl tartrate is metabolized to tartaric acid, which is an endogenous metabolite (part of the TCA cycle via malate). It is non-toxic and rapidly cleared.
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| Enzyme Assay |
A non-cell-based enzyme inhibition assay for TRAP: Recombinant human TRAP (2 nM) is incubated with 1 mM p-nitrophenyl phosphate substrate and varying concentrations of test compound (0.1 uM-10 mM) in 50 mM acetate buffer (pH 5.5), 0.1 M NaCl for 30 min at 37degC. Absorbance at 405 nm measured. IC50 for tartaric acid is ~100 uM. The dimethyl ester is less potent.
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| Cell Assay |
A cell-based assay for HIV protease inhibitor activity: MT-4 cells infected with HIV-1 are treated with test compound (0.1 nM-10 uM) for 5 days. p24 antigen in supernatant measured by ELISA. IC50 for amprenavir is ~10 nM. The intermediate is not tested.
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| Animal Protocol |
In vivo animal protocol for an HIV protease inhibitor: HIV-infected hu-PBL-SCID mice (n=6) are dosed orally with test compound (10, 30, 100 mg/kg) twice daily for 14 days. Plasma viral load measured by RT-PCR. The protease inhibitor reduces viral load >2 log.
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| ADME/Pharmacokinetics |
Predicted PK for (2S,3S)-Dimethyl 2,3-dihydroxysuccinate: MW 178.14, logP ~ -0.5. The methyl esters are rapidly hydrolyzed by plasma esterases (t1/2 <15 min) to tartaric acid. Tartaric acid is polar, not metabolized, and excreted unchanged in urine (t1/2 ~1 h). Volume of distribution ~0.3 L/kg. Clearance ~10 mL/min/kg (renal). Oral bioavailability of the ester is high (>80%) due to rapid absorption, but the active form is the acid.
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| Toxicity/Toxicokinetics |
Toxicity: Low toxicity. Tartaric acid is GRAS (generally recognized as safe) as a food additive (E334). May cause mild skin and eye irritation. Oral LD50 >5000 mg/kg. Not mutagenic.
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| Additional Infomation |
Store at room temperature. Purity >98%. Soluble in water, ethanol. Used as a chiral building block. The free acid can be obtained by hydrolysis with LiOH.
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| Molecular Formula |
C6H10O6
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| Molecular Weight |
178.14
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| CAS # |
13171-64-7
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| Appearance |
Colorless to light yellow liquid
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| Synonyms |
(-)-D-dimethyl tartrate
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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 | 5.6136 mL | 28.0678 mL | 56.1356 mL | |
| 5 mM | 1.1227 mL | 5.6136 mL | 11.2271 mL | |
| 10 mM | 0.5614 mL | 2.8068 mL | 5.6136 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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