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| 5mg |
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| 10mg |
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| Targets |
Penetratin primarily targets the plasma membrane of eukaryotic cells. Its mechanism of action involves direct translocation across lipid bilayers via an energy-independent pathway, potentially involving membrane destabilization and inverted micelle formation, allowing it to deliver conjugated or complexed cargo into the cytoplasm and nucleus.
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| ln Vitro |
In vitro, Penetratin shows low cytotoxicity against NHC cells with an IC50 higher than 2.5 mM. At concentrations of 57-285 microM, it significantly increases cellular uptake of various molecules. It also enhances corneal permeation ability and facilitates the intracellular delivery of drugs, nanoparticles, and fluorescent probes in a variety of cell lines.
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| ln Vivo |
In vivo, Penetratin shows long-lasting retention in ocular tissues following conjunctival administration (570 microM, three times with 10-minute intervals). It also increases the retention of single-chain variable fragments (scFvs) in LS174T tumor-bearing mouse models when administered intravenously (12.5 microM), demonstrating its utility as a delivery-enhancing agent.
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| Enzyme Assay |
Penetratin's membrane activity is assessed using lipid vesicle leakage or dye encapsulation assays. Liposomes encapsulating a fluorescent dye (e.g., calcein) are prepared. Penetratin is added at varying concentrations, and fluorescence increase due to dye release upon membrane disruption is measured. This non-cellular assay quantifies the peptide‘s membrane-permeating efficiency.
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| Cell Assay |
The standard cellular assay measures Penetratin's cell-penetrating efficiency using fluorescence microscopy or flow cytometry. Cells (e.g., HeLa or CHO) are incubated with a fluorescently-labeled Penetratin (e.g., FITC-Penetratin) at 37degC for 30-120 minutes. After washing to remove surface-bound peptide, the mean fluorescence intensity (MFI) is quantified to determine cellular uptake, often in the presence or absence of endocytosis inhibitors to elucidate the uptake mechanism.
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| Animal Protocol |
Mice are used to evaluate Penetratin‘s in vivo delivery capability. A fluorescently-labeled or drug-conjugated Penetratin is administered via a chosen route (e.g., conjunctival instillation for ocular delivery, intravenous injection for tumor targeting). After 1-24 hours, relevant tissues (cornea, conjunctiva, or tumor) are collected, sectioned, and examined under a fluorescence microscope to assess retention and biodistribution of the delivered cargo.
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| ADME/Pharmacokinetics |
Penetratin has a molecular weight of 2360.83 Da (C108H174N36O22S). It is freely soluble in water (90 mg/mL). As a peptide, it is rapidly degraded by proteases in serum and tissues; therefore, its plasma half-life is typically short (minutes). For enhanced stability, it is often stored as a powder at -20degC and protected from light.
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| Toxicity/Toxicokinetics |
Systemic toxicity of Penetratin is low at concentrations used for drug delivery (e.g., up to 570 uM in vivo). In vitro, it shows low cytotoxicity with an IC50 >2.5 mM. Local administration (e.g., conjunctival) is well-tolerated. However, as a membrane-active peptide, very high concentrations could potentially disrupt cell membranes and cause non-specific cytotoxicity.
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| References |
[1]. Jianzhong Wen, et al. Quantitation of Super Basic Peptides in Biological Matrices by a Generic Perfluoropentanoic Acid-Based Liquid Chromatography-Mass Spectrometry Method. J Am Soc Mass Spectrom. 2019 Sep;30(9):1779-1789.
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| Additional Infomation |
galparan (C107160) analogue, which can be used as a carrier for hydrophilic molecules, is named transportan; its amino acid sequence is known. A drug carrier derived from Drosophila antennal protein.
Penetratin's sequence is RQIKIWFQNRRMKWKK. It was first described in 1994 and has since become a standard tool for intracellular delivery in cell biology. It is not a therapeutic agent itself but serves as a delivery vehicle for research applications. It is not approved by the FDA for clinical use, and its use in humans remains experimental. |
| Molecular Formula |
C108H174N36O22S
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|---|---|
| Molecular Weight |
2360.83017969131
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| Exact Mass |
2360.335
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| CAS # |
940866-75-1
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| PubChem CID |
168013270
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| Appearance |
White to off-white solid powder
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| LogP |
-7.1
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| Hydrogen Bond Donor Count |
37
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| Hydrogen Bond Acceptor Count |
31
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| Rotatable Bond Count |
87
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| Heavy Atom Count |
167
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| Complexity |
4980
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| Defined Atom Stereocenter Count |
18
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| SMILES |
CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC4=CNC5=CC=CC=C54)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)NCC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCNC(=N)N)N
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| InChi Key |
OWTCNGRIGAUCBN-IQXNUNNASA-N
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| InChi Code |
InChI=1S/C108H174N36O22S/c1-6-60(3)88(144-99(160)77(40-42-84(115)146)130-90(151)67(113)30-23-48-123-106(117)118)104(165)138-73(36-18-22-47-112)98(159)143-89(61(4)7-2)105(166)142-81(54-64-57-127-69-32-14-12-29-66(64)69)102(163)139-79(52-62-26-9-8-10-27-62)100(161)136-76(39-41-83(114)145)96(157)141-82(55-85(116)147)103(164)135-75(38-25-50-125-108(121)122)93(154)133-74(37-24-49-124-107(119)120)94(155)137-78(43-51-167-5)97(158)132-72(35-17-21-46-111)95(156)140-80(53-63-56-126-68-31-13-11-28-65(63)68)101(162)134-71(34-16-20-45-110)92(153)131-70(33-15-19-44-109)91(152)129-58-86(148)128-59-87(149)150/h8-14,26-29,31-32,56-57,60-61,67,70-82,88-89,126-127H,6-7,15-25,30,33-55,58-59,109-113H2,1-5H3,(H2,114,145)(H2,115,146)(H2,116,147)(H,128,148)(H,129,152)(H,130,151)(H,131,153)(H,132,158)(H,133,154)(H,134,162)(H,135,164)(H,136,161)(H,137,155)(H,138,165)(H,139,163)(H,140,156)(H,141,157)(H,142,166)(H,143,159)(H,144,160)(H,149,150)(H4,117,118,123)(H4,119,120,124)(H4,121,122,125)/t60-,61-,67-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,88-,89-/m0/s1
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| Chemical Name |
2-[[2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-6-amino-2-[[(2S,3S)-2-[[(2S)-5-amino-2-[[(2S)-2-amino-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]amino]hexanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenylpropanoyl]amino]-5-oxopentanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-methylsulfanylbutanoyl]amino]hexanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]hexanoyl]amino]hexanoyl]amino]acetyl]amino]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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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) |
H2O: 100 mg/mL (42.36 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 | 0.4236 mL | 2.1179 mL | 4.2358 mL | |
| 5 mM | 0.0847 mL | 0.4236 mL | 0.8472 mL | |
| 10 mM | 0.0424 mL | 0.2118 mL | 0.4236 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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