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| Targets |
1-Boc-4-carboxymethyl piperazine is a PROTAC linker and has no direct biological target. As a PROTAC linker, it serves as a spacer connecting an E3 ubiquitin ligase ligand (e.g., CRBN or VHL) to a target protein ligand. The piperazine ring provides conformational flexibility and can improve the solubility of the PROTAC molecule. The Boc group protects the piperazine nitrogen during synthesis and can be removed under acidic conditions to reveal a secondary amine for further conjugation. The carboxymethyl group (CH2COOH) can be activated (e.g., to an NHS ester) for amide bond formation with amine-containing ligands. This linker has been used to synthesize PROTAC IRAK4 degrader-12.
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| ln Vitro |
The compound itself has no direct in vitro biological activity. It is a chemical building block for PROTAC synthesis. Its activity is assessed after conjugation to an E3 ligase ligand and a target protein ligand. The resulting PROTAC is then evaluated for its ability to induce target protein degradation in cells. The piperazine linker enhances solubility and may improve the cell permeability of the PROTAC.
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| ln Vivo |
The compound is not a drug; it is a PROTAC linker. PROTACs synthesized using this linker can have potent in vivo activity. In xenograft mouse models, PROTACs are administered intraperitoneally or intravenously (10-100 mg/kg) once daily for 2-4 weeks. They induce sustained degradation of target proteins in tumors (>80% reduction) and inhibit tumor growth. This linker has been used in the development of PROTAC IRAK4 degrader-12.
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| Enzyme Assay |
Not applicable. 1-Boc-4-carboxymethyl piperazine is a PROTAC linker, not a standard enzyme inhibitor. Its purity (>97-98%) is assessed by HPLC. The structure is confirmed by ¹H NMR (Boc group delta 1.4-1.5 ppm, piperazine protons delta 2.4-3.5 ppm, CH2 delta 3.2 ppm, COOH delta 12.0-12.5 ppm) and mass spectrometry (ESI-MS, expected [M+H]+ m/z 245). Physicochemical properties: MW 244.29, off-white to gray solid powder, soluble in DMSO, stored at 2-8degC. No biological assays are applicable.
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| Cell Assay |
Not applicable. 1-Boc-4-carboxymethyl piperazine is not used directly in cell-based assays; it is a building block for PROTAC synthesis. For PROTAC evaluation, cells expressing the target protein are seeded in 6-well plates (3×10⁵ cells/well) and treated with the PROTAC (0.1-1000 nM) for 4-24 h. Target protein degradation is assessed by Western blotting. DC₅0 is calculated from the dose-response curve. Cell viability is measured by MTT or CellTiter-Glo.
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| Animal Protocol |
In vivo efficacy of PROTACs incorporating 1-Boc-4-carboxymethyl piperazine can be evaluated in xenograft mouse models. For example, PROTAC IRAK4 degrader-12, which uses this linker, has been studied. Female BALB/c nude mice (6-8 wk) are subcutaneously inoculated with 5×10⁶ cancer cells. When tumors reach ~100-150 mm3, mice are randomized into treatment groups (n=6-8/group). The PROTAC is formulated in 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% saline and administered intraperitoneally at 10-100 mg/kg once daily or every other day for 2-4 weeks. Tumor volume is measured every 3 days with calipers, and tumors are excised for Western blot analysis of target protein levels.
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| ADME/Pharmacokinetics |
No specific PK data is available for 1-Boc-4-carboxymethyl piperazine alone. When incorporated into a PROTAC (MW 800-1200), the overall PK properties are determined by the full PROTAC molecule. PROTACs generally have moderate to low oral bioavailability (<20%), short plasma half-life (1-4 h), high plasma protein binding (>90%), and rapid clearance. The piperazine linker improves solubility and may increase the metabolic stability of the PROTAC.
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| Toxicity/Toxicokinetics |
For 1-Boc-4-carboxymethyl piperazine, hazard statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation). Signal word: Warning. Precautionary statements: P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). Storage: at 2-8degC, sealed, protect from light.
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| References | |
| Additional Infomation |
1-Boc-4-carboxymethyl piperazine (4-Boc-1-piperazineacetic acid; CAS# 156478-71-6) is a research-grade PROTAC linker and chemical building block. It is not an FDA-approved drug. For research and industrial synthesis use only, not for diagnostic or therapeutic applications.
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| Molecular Formula |
C11H20N2O4
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|---|---|
| Molecular Weight |
244.29
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| Exact Mass |
244.142
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| CAS # |
156478-71-6
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| PubChem CID |
2735642
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| Appearance |
Off-white to gray solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
365.5±37.0 °C at 760 mmHg
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| Flash Point |
174.9±26.5 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.501
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| LogP |
0.92
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
17
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| Complexity |
290
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)(C)OC(=O)N1CCN(CC(O)=O)CC1
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| InChi Key |
WZBHMXRBXXCEDD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H20N2O4/c1-11(2,3)17-10(16)13-6-4-12(5-7-13)8-9(14)15/h4-8H2,1-3H3,(H,14,15)
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| Chemical Name |
2-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]acetic acid
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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 | 4.0935 mL | 20.4675 mL | 40.9350 mL | |
| 5 mM | 0.8187 mL | 4.0935 mL | 8.1870 mL | |
| 10 mM | 0.4093 mL | 2.0467 mL | 4.0935 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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