| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
None (excipient). DSPE-Thiol is a functionalized phospholipid used to incorporate free thiol (-SH) groups onto liposome or LNP surfaces. Thiol groups react with maleimide, iodoacetamide, or disulfide exchange chemistries, enabling covalent conjugation of thiol-reactive ligands for targeted drug delivery applications.
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|---|---|
| ln Vitro |
DSPE-Thiol liposomes are stable and can be functionalized with targeting ligands via maleimide-thiol conjugation. In vitro, antibody-conjugated DSPE-Thiol liposomes show increased cellular uptake and enhanced cytotoxicity in target cells expressing the corresponding antigen. The conjugation efficiency typically exceeds 70-80%. DSPE-Thiol can be incorporated into liposomes at 1-10 mol%.
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| ln Vivo |
DSPE-Thiol liposomes have been evaluated in vivo for targeted drug delivery. Antibody-targeted DSPE-Thiol liposomes encapsulating chemotherapeutic agents show enhanced tumor accumulation and improved therapeutic efficacy in mouse xenograft models compared to non-targeted liposomes. The free thiol group is typically protected (e.g., as a disulfide or thioacetate) during formulation and deprotected before conjugation. The saturated DSPE acyl chains (C18:0) provide resistance to phospholipase degradation, prolonging circulation time.
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| Enzyme Assay |
DSPE-Thiol (CAS 144735-82-0) is typically supplied as a disulfide-protected form (e.g., DSPE-S-S-Pyridine). For use, the disulfide is reduced with TCEP or DTT to generate free thiol groups. For liposome preparation: DSPE-Thiol (after deprotection) is mixed with other lipids (e.g., DOPC/DSPC, cholesterol, PEG2000-DSPE) in chloroform (typical molar ratio 5-10% for DSPE-Thiol). The mixture is dried, hydrated with buffer (degassed PBS, pH 6.5-7.0, containing 1-2 mM EDTA to prevent oxidation), and extruded (50-200 nm pores) to form Thiol-liposomes. For ligand conjugation: maleimide-activated ligands (e.g., maleimide-PEG-antibody, maleimide-peptide) are incubated with Thiol-liposomes (ligand:thiol ratio 1:2-1:5) at room temperature for 2-4 h at pH 6.5-7.0 (optimal maleimide-thiol reaction pH). The reaction is quenched with excess cysteine or glutathione, and free thiols are capped with iodoacetamide. Conjugation efficiency is measured by HPLC, Ellman's assay (for free thiols), or SDS-PAGE.
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| Cell Assay |
For cellular uptake studies, cancer cells (e.g., SK-BR-3, MDA-MB-231) are seeded in 96- or 24-well plates (1-5×10⁴ cells/well) and treated with ligand-conjugated DSPE-Thiol liposomes or non-targeted liposomes (0.1-1 mg/mL total lipid) containing a fluorescent dye (e.g., DiD, Rhodamine). After 2-24 h, cellular uptake is quantified by flow cytometry, and intracellular localization is visualized by confocal microscopy. Cytotoxicity is evaluated by MTT assays; ligand-targeted liposomes may show enhanced cytotoxicity due to increased drug delivery. For immunotoxicity, complement activation is measured by ELISA (C3a, C5a).
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| Animal Protocol |
DSPE-Thiol liposomes (typically as part of PEGylated long-circulating liposomes) are administered intravenously via the tail vein to 6-8 week old female BALB/c nude or C57BL/6 mice at lipid doses of 10-50 mg/kg, with encapsulated chemotherapeutics (e.g., doxorubicin 2-5 mg/kg). Tumor volume is measured every 2-3 days, and TGI is calculated. For biodistribution: mice are euthanized at 1, 4, 24, 48, 72 h; organs (liver, spleen, kidney, lung, tumor) are harvested, homogenized, and analyzed for drug content by HPLC. Pharmacodynamics are assessed by tumor immunohistochemistry (Ki67, TUNEL). Free thiols may react with plasma thiols (e.g., albumin) if not conjugated, potentially leading to rapid clearance; thus, full conjugation is critical.
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| ADME/Pharmacokinetics |
DSPE-Thiol, incorporated into PEGylated liposomes (with PEG2000-DSPE), extends circulation half-life to 6-12 h. The saturated DSPE acyl chains (C18:0) increase membrane rigidity and resistance to phospholipase degradation, enhancing plasma stability. Thiol groups, if left unconjugated, are susceptible to oxidation to form disulfides (DSPE-S-S-DSPE), which can cause liposome aggregation. In circulation, free thiols may react with plasma proteins, leading to opsonization and faster clearance. Ligand conjugation via maleimide-thiol chemistry is stable for at least 24-48 h in circulation. Liposomes are cleared primarily by the liver (∼30-50% of dose) and spleen (∼10-20%).
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| Toxicity/Toxicokinetics |
DSPE-Thiol itself is not toxic; however, free thiol groups in liposomes may react with plasma proteins, leading to opsonization and potential immunogenicity. If not properly conjugated, free thiols can cause complement activation or thrombocytopenia at high doses. In practice, DSPE-Thiol is conjugated to ligands before administration, minimizing free thiol exposure. Standard PEGylated liposome safety applies: potential for CARPA, mild hepatotoxicity (transient ALT/AST elevation), and splenic accumulation. No severe toxicity has been reported at therapeutic doses.
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| References | |
| Additional Infomation |
DSPE-Thiol (CAS 144735-82-0, molecular weight ∼750-1000 Da) has >95% purity and is a white to off-white solid powder. Storage at -20degC under inert atmosphere (N2 or Ar) to prevent oxidation. DSPE-Thiol is typically supplied as a disulfide-protected form (e.g., DSPE-S-S-Pyridine) or as a free thiol (less stable). It is soluble in chloroform and DMSO. DSPE-Thiol is used in research for preparing targeted liposomes and LNPs, and for conjugating maleimide-activated ligands (antibodies, peptides, PEG). No clinical approvals have been reported.
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| Molecular Formula |
C44H86NO9PS
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|---|---|
| Molecular Weight |
836.19
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| Exact Mass |
835.576
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| CAS # |
144735-82-0
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| PubChem CID |
15087996
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| Appearance |
White to off-white solid powder
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
46
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| Heavy Atom Count |
56
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| Complexity |
957
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCNC(=O)CCS)OC(=O)CCCCCCCCCCCCCCCCC
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| InChi Key |
VPGMYYHJMRLITI-VQJSHJPSSA-N
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| InChi Code |
InChI=1S/C44H86NO9PS/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-43(47)51-39-41(40-53-55(49,50)52-37-36-45-42(46)35-38-56)54-44(48)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h41,56H,3-40H2,1-2H3,(H,45,46)(H,49,50)/t41-/m1/s1
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| Chemical Name |
[(2R)-3-[hydroxy-[2-(3-sulfanylpropanoylamino)ethoxy]phosphoryl]oxy-2-octadecanoyloxypropyl] octadecanoate
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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) |
DMF: 2 mg/mL (2.39 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 | 1.1959 mL | 5.9795 mL | 11.9590 mL | |
| 5 mM | 0.2392 mL | 1.1959 mL | 2.3918 mL | |
| 10 mM | 0.1196 mL | 0.5980 mL | 1.1959 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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