| Size | Price | Stock | Qty |
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| 500mg |
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| 1g |
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| Other Sizes |
| Targets |
Fmoc-(R)-2-(7-octenyl)Ala-OH itself has no biological target. It is a synthetic amino acid used to construct bioactive peptides. The peptides that incorporate this building block can be designed to target various protein-protein interactions. As stated in the search results, it is used to synthesize inhibitor peptides that can combinatorially inactivate ErbB1, ErbB2, and ErbB3 (EGFR family). Its target is determined by the final stapled peptide sequence.
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| ln Vitro |
Specific in vitro activity data for the compound itself is not available. Its value lies in its role as a building block for creating stapled alpha-helical peptides that can penetrate cells and inhibit specific protein-protein interactions. For instance, a stapled peptide incorporating this residue could block the dimerization of ErbB receptors, leading to inhibition of downstream signaling and anti-proliferative effects in cancer cells. The biological activity is attributed to the final peptide, not the individual amino acid building block.
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| ln Vivo |
Not applicable. The compound itself is not administered in vivo. However, stapled peptides synthesized using this building block have been shown to be more stable and cell-permeable than their linear counterparts, making them suitable for in vivo applications. These stapled peptides have demonstrated the ability to disrupt intracellular protein-protein interactions and exhibit anti-tumor activity in animal models. This building block is a critical tool for enabling such in vivo efficacy.
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| Enzyme Assay |
Not applicable. Fmoc-(R)-2-(7-octenyl)Ala-OH is not used in biological binding assays. It is a chemical reagent for peptide synthesis. Its reactivity is utilized in the ring-closing metathesis (RCM) reaction to create all-hydrocarbon "staples" between two alkenyl side chains within a peptide. A typical procedure involves dissolving the resin-bound peptide containing two alkene-bearing amino acids (e.g., Fmoc-(R)-2-(7-octenyl)Ala-OH and another S-pentenylalanine) in degassed DCE. Grubbs catalyst (first or second generation) is added, and the reaction is stirred at room temperature for 2-8 hours. The stapled peptide is then cleaved from the resin and purified by HPLC.
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| Cell Assay |
Not applicable. Fmoc-(R)-2-(7-octenyl)Ala-OH is not tested on cells directly. However, the final stapled peptides that incorporate this building block can be tested in cellular assays. Procedure: Cancer cells (e.g., ErbB2-positive breast cancer SK-BR-3 cells) are seeded in 96-well plates and treated with varying concentrations (0.1-10 microM) of the stapled peptide for 48-72 hours. Cell viability is measured using CellTiter-Glo or MTT assay. To assess target engagement, cells are treated for 6 hours, and cell lysates are analyzed by Western blotting for levels of phospho-EGFR, phospho-AKT, and phospho-ERK, which are downstream readouts of ErbB receptor activity.
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| Animal Protocol |
The in vivo efficacy of the final stapled peptide can be evaluated in a mouse xenograft model of ErbB2-positive breast cancer. Procedure: Female athymic nude mice are inoculated subcutaneously with 5x10^6 SK-BR-3 cells. When tumors reach 100-150 mm3, mice are randomized (n=8/group). The stapled peptide is dissolved in PBS or a suitable formulation (e.g., 5% glucose) and administered intraperitoneally (IP) or intravenously (IV) at a dose of 10-20 mg/kg, daily or every other day, for 2-3 weeks. Tumor volumes are measured twice weekly. Blood is collected to measure peptide stability and PK. Tumors are harvested for analysis of target inhibition by Western blotting and for IHC with Ki-67 and cleaved caspase-3.
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| ADME/Pharmacokinetics |
Not applicable. The compound is a synthetic building block, not a drug. The pharmacokinetics of the final stapled peptide (which incorporates this building block) would be studied. Stapling generally improves the pharmacokinetic profile of peptides by increasing their proteolytic stability and half-life. The presence of the lipophilic octenyl side chain can also enhance membrane permeability and tissue distribution. The specific PK parameters would be determined by the overall structure of the stapled peptide.
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| Toxicity/Toxicokinetics |
Specific toxicity data for Fmoc-(R)-2-(7-octenyl)Ala-OH is not available. As a Fmoc-protected amino acid derivative, it is a chemical reagent intended for research use only and should be handled with standard precautions. Direct exposure should be avoided as it may cause skin or eye irritation. It is not intended for human or animal consumption. The final stapled peptide would require its own toxicological assessment.
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| References | |
| Additional Infomation |
Fmoc-(R)-2-(7-octenyl)Ala-OH is a sophisticated tool for the synthesis of "stapled peptides." This chemical strategy is used to lock peptides, which are normally flexible and susceptible to proteolysis, into a stable alpha-helical conformation. The stapling is achieved via a ring-closing metathesis reaction between the octenyl side chain of this building block and a shorter alkenyl side chain from another amino acid in the peptide sequence. This technology has revolutionized the development of peptide therapeutics by enabling them to target intracellular protein-protein interactions that are traditionally considered "undruggable." This product is for research use only.
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| Molecular Formula |
C26H31NO4
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|---|---|
| Molecular Weight |
421.53
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| Exact Mass |
421.225
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| CAS # |
945212-26-0
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| PubChem CID |
45489836
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| Appearance |
Off-white to yellow Solid-Liquid Mixture
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| Density |
1.14
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| Boiling Point |
588.348ºC at 760 mmHg
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| Flash Point |
309.622ºC
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| Index of Refraction |
1.567
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| LogP |
6.286
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
12
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| Heavy Atom Count |
31
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| Complexity |
599
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C(C1C2C=CC=CC=2C2C=CC=CC1=2)OC(=O)N[C@@](C)(C(=O)O)CCCCCCC=C
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| InChi Key |
MADFVGMQNXRFAF-AREMUKBSSA-N
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| InChi Code |
InChI=1S/C26H31NO4/c1-3-4-5-6-7-12-17-26(2,24(28)29)27-25(30)31-18-23-21-15-10-8-13-19(21)20-14-9-11-16-22(20)23/h3,8-11,13-16,23H,1,4-7,12,17-18H2,2H3,(H,27,30)(H,28,29)/t26-/m1/s1
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| Chemical Name |
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyldec-9-enoic 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 Note: (1). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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 | 2.3723 mL | 11.8616 mL | 23.7231 mL | |
| 5 mM | 0.4745 mL | 2.3723 mL | 4.7446 mL | |
| 10 mM | 0.2372 mL | 1.1862 mL | 2.3723 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
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