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| Other Sizes |
| Targets |
Fmoc-Phe(4-I)-OH primarily targets dipeptidyl peptidase 4 in humans and aminopeptidase S in Streptomyces griseus. These enzymes play crucial roles in protein metabolism and regulation. As a phenylalanine derivative, it also falls within the broader category of amino acid derivatives as molecular targets. The compound's action is largely dependent on the specific peptides into which it is incorporated; the Phe(4-I) residue can be converted into a wide variety of substituted phenylalanines, potentially leading to diverse effects at the molecular level.
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| ln Vitro |
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
As a phenylalanine derivative, Fmoc-Phe(4-I)-OH has been recognized in the context of amino acid and amino acid derivative research. Amino acids and their derivatives have been commercially used as ergogenic supplements, influencing the secretion of anabolic hormones, the supply of fuel for activity, mental performance under stress, and the prevention of exercise-induced muscle damage. They are regarded as beneficial synergistic food ingredients. The compound can be converted to phosphophenylalanine or the protected phosphotyrosine analog F2Pmp, suggesting interactions with enzymes involved in phosphorylation reactions. |
| ln Vivo |
Specific in vivo activity data for Fmoc-Phe(4-I)-OH as a standalone compound are not extensively documented in the literature. As a specialized building block for peptide synthesis, its in vivo effects are primarily determined by the biological activities of the final peptide or conjugate into which it is incorporated. The iodine handle enables the synthesis of radiolabeled peptides for in vivo imaging applications such as SPECT, where the incorporated iodine isotope (I-123 or I-125) serves as the imaging probe. The compound's in vivo behavior would therefore be dictated by the pharmacokinetic and targeting properties of the specific peptide construct.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for Fmoc-Phe(4-I)-OH typically involve evaluating its role as a building block in peptide synthesis rather than direct enzyme binding. However, when incorporated into peptides, the resulting iodinated peptides can be assessed for target binding affinity using standard radioligand binding assays or surface plasmon resonance (SPR). The compound can be converted to phosphophenylalanine or F2Pmp, enabling studies on phosphatase inhibition. Typical assay conditions involve buffered aqueous solutions at physiological pH, with binding affinity expressed as IC₅₀ or Kd values determined through competitive binding experiments.
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| Cell Assay |
In vitro cell-based studies using Fmoc-Phe(4-I)-OH typically focus on evaluating the biological activities of peptides synthesized with this building block rather than the compound itself. When incorporated into peptides, the resulting constructs can be assessed in various cell-based assays including proliferation assays (e.g., MTT), receptor binding and internalization studies, and functional readouts such as calcium flux or reporter gene activation. For iodinated peptides, cellular uptake and intracellular trafficking can be monitored using radiolabeled or fluorescently labeled derivatives. Standard cell culture conditions (37°C, 5% CO₂) with appropriate cell lines are employed depending on the biological target of interest.
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| Animal Protocol |
In vivo animal studies using Fmoc-Phe(4-I)-OH are conducted with peptides or conjugates synthesized from this building block rather than the compound itself. The iodine handle enables radio-labeling with isotopes such as I-123 or I-125 for SPECT imaging studies in animal models. Typical experimental designs involve administration of the radiolabeled peptide to rodents (e.g., mice or rats) via intravenous injection, followed by imaging at various time points to assess biodistribution, target engagement, and clearance. Biodistribution studies may also involve ex vivo organ counting to quantify tissue accumulation. All procedures must comply with institutional animal care and use guidelines.
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| ADME/Pharmacokinetics |
Specific pharmacokinetic data for Fmoc-Phe(4-I)-OH as a standalone compound are not well characterized. The compound is known to be sparingly soluble in water, which may impact its absorption and distribution. Its solubility can be influenced by pH and temperature of the environment. When incorporated into peptides, the pharmacokinetic properties are determined by the overall peptide construct, including factors such as molecular weight, charge, hydrophobicity, and stability toward proteolytic degradation. The Fmoc protecting group is typically removed during peptide synthesis, so the final peptide's PK profile is the primary consideration for in vivo applications.
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| Toxicity/Toxicokinetics |
Toxicological data for Fmoc-Phe(4-I)-OH as a standalone compound are not extensively documented. The compound is intended for research use only and is not approved for human or veterinary use. Standard safety precautions should be observed when handling this compound, including the use of appropriate personal protective equipment. As an iodine-containing compound, its toxicity profile may be influenced by the iodine moiety, though the Fmoc protecting group is typically removed during peptide synthesis. For peptides synthesized using this building block, standard toxicological assessments would be performed on the final peptide product rather than on the individual amino acid building block.
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| References | |
| Additional Infomation |
Fmoc-Phe(4-I)-OH (CAS#: 82565-68-2) has a molecular formula of C₂₄H₂₀INO₄ and a molecular weight of 513.32 g/mol. Its IUPAC name is (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-iodophenyl)propanoic acid. The compound is typically stored as a powder at -20°C (stable for 3 years) or 4°C (stable for 2 years); in solvent, it can be stored at -80°C for 6 months or -20°C for 1 month. It is soluble in DMSO at 62 mg/mL with ultrasonic assistance. The Fmoc group enables selective deprotection under mild basic conditions (e.g., piperidine in DMF), allowing peptide chain elongation in SPPS. The para-iodo substituent provides a versatile handle for post-synthetic modifications including cross-coupling reactions and radio-labeling. This compound is not a drug and has not undergone clinical trials or received regulatory approval for therapeutic use; it is strictly a research reagent for peptide synthesis and chemical biology applications.
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| Molecular Formula |
C24H20INO4
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|---|---|
| Molecular Weight |
513.32
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| Exact Mass |
513.043
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| CAS # |
82565-68-2
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| PubChem CID |
2761479
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
658.8±55.0 °C at 760 mmHg
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| Melting Point |
213-217 °C(lit.)
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| Flash Point |
352.2±31.5 °C
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| Vapour Pressure |
0.0±2.1 mmHg at 25°C
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| Index of Refraction |
1.668
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| LogP |
6.44
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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 |
7
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| Heavy Atom Count |
30
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| Complexity |
584
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C(C1C2=CC=CC=C2C2C=CC=CC1=2)OC(=O)N[C@H](C(=O)O)CC1C=CC(I)=CC=1
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| InChi Key |
LXOXXTQKKRJNNB-QFIPXVFZSA-N
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| InChi Code |
InChI=1S/C24H20INO4/c25-16-11-9-15(10-12-16)13-22(23(27)28)26-24(29)30-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/t22-/m0/s1
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| Chemical Name |
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-iodophenyl)propanoic 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) |
DMSO: 62.5 mg/mL (121.76 mM)
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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 | 1.9481 mL | 9.7405 mL | 19.4810 mL | |
| 5 mM | 0.3896 mL | 1.9481 mL | 3.8962 mL | |
| 10 mM | 0.1948 mL | 0.9741 mL | 1.9481 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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