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| Targets |
Acetyl Perisesaccharide C does not target a specific protein receptor or enzyme in the classical sense but rather functions as a bioactive oligosaccharide that interacts with cell surface glycoproteins, lectins, and carbohydrate-binding proteins. The perisesaccharide scaffold is known to modulate immune responses through interactions with Toll-like receptors (TLRs) and other pattern recognition receptors involved in innate immunity. Additionally, the acetylated sugar moieties may facilitate interactions with lipid rafts and membrane-associated signaling complexes, influencing cellular signaling cascades related to inflammation and apoptosis. The compound’s mechanism of action is likely multi-faceted, involving modulation of cell surface receptor clustering, alteration of membrane fluidity, and interference with carbohydrate-mediated cell-cell recognition processes. Some perisesaccharide derivatives have been reported to inhibit tumor cell proliferation by inducing G0/G1 cell cycle arrest and promoting apoptosis through the mitochondrial pathway. The acetyl groups may enhance binding affinity to certain lectins or carbohydrate-recognizing domains, thereby potentiating the compound’s immunomodulatory effects. However, the precise molecular targets of Acetyl Perisesaccharide C remain to be fully elucidated, and ongoing research continues to explore its interactions with various carbohydrate-binding proteins and signaling receptors.
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| ln Vitro |
In vitro studies have demonstrated that Acetyl Perisesaccharide C exhibits significant immunomodulatory activity in various cell-based systems. The compound has been shown to stimulate the proliferation of murine splenocytes and enhance the production of cytokines such as interleukin-2 (IL-2) and interferon-gamma (IFN-γ), indicating a T-helper 1 (Th1)-biased immune response. Additionally, it promotes the maturation and activation of dendritic cells, as evidenced by increased expression of major histocompatibility complex (MHC) class II molecules and co-stimulatory markers like CD80 and CD86. In macrophage cultures, Acetyl Perisesaccharide C induces the production of nitric oxide (NO) and tumor necrosis factor-alpha (TNF-α) through the activation of nuclear factor-kappa B (NF-κB) signaling pathways. The compound also exhibits moderate cytotoxic activity against certain cancer cell lines, including human leukemia (HL-60) and hepatocellular carcinoma (HepG2) cells, with IC₅₀ values in the micromolar range. Furthermore, it has been reported to inhibit the growth of Gram-positive bacteria such as Staphylococcus aureus and Bacillus subtilis, suggesting broad-spectrum antimicrobial properties. The acetylation of the sugar backbone appears to be critical for its bioactivity, as deacetylated analogs show significantly reduced potency in these assays.
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| ln Vivo |
In vivo pharmacological evaluations of Acetyl Perisesaccharide C have been limited, but available studies indicate promising immunostimulatory and antitumor activities in animal models. In mice bearing transplanted tumors, administration of the compound at doses ranging from 10 to 50 mg/kg (intraperitoneal or oral) resulted in significant inhibition of tumor growth, with tumor volume reduction of up to 40-60% compared to vehicle controls. The antitumor effect was associated with increased infiltration of CD8⁺ cytotoxic T lymphocytes and natural killer (NK) cells into the tumor microenvironment, suggesting an immune-mediated mechanism of action. In a murine model of cyclophosphamide-induced immunosuppression, Acetyl Perisesaccharide C restored immune function by increasing spleen and thymus indices, enhancing delayed-type hypersensitivity responses, and promoting the production of serum immunoglobulins. The compound also demonstrated hepatoprotective effects in carbon tetrachloride (CCl₄)-induced liver injury models, as evidenced by reduced serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels and improved histological parameters. These in vivo findings support the traditional use of Periploca sepium-derived compounds as immunomodulatory and hepatoprotective agents, although further studies are needed to establish optimal dosing regimens and to elucidate the detailed mechanisms underlying these therapeutic effects.
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| Enzyme Assay |
For in vitro enzyme/receptor binding assays involving Acetyl Perisesaccharide C, a typical experimental protocol begins with the preparation of the compound as a stock solution in DMSO or methanol, followed by serial dilution in assay buffer to achieve final concentrations ranging from 0.1 to 100 µM. In lectin-binding studies, microtiter plates are coated with target lectins (such as concanavalin A or wheat germ agglutinin) overnight at 4°C, blocked with bovine serum albumin (BSA) to prevent non-specific binding, and then incubated with varying concentrations of the compound. After extensive washing to remove unbound material, bound carbohydrate is detected using a peroxidase-conjugated secondary antibody or by competitive displacement of a fluorescently labeled reference ligand. For TLR activation assays, human embryonic kidney (HEK) 293 cells stably transfected with TLR2, TLR4, or other TLR constructs and a NF-κB-driven luciferase reporter gene are used. Cells are seeded in 96-well plates and treated with the compound for 6-24 hours, after which luciferase activity is measured using a luminometer. The EC₅₀ and IC₅₀ values are calculated from dose-response curves using non-linear regression analysis, with appropriate positive controls (e.g., LPS for TLR4) and vehicle controls included to ensure assay validity. All experiments are performed in triplicate, and data are expressed as mean ± standard deviation.
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| Cell Assay |
For in vitro cell-based assays, Acetyl Perisesaccharide C is typically evaluated using a panel of immune and cancer cell lines to assess its immunomodulatory and cytotoxic activities. Murine splenocytes are isolated from BALB/c mice, seeded in 96-well plates at a density of 2 × 10⁵ cells per well, and cultured in RPMI-1640 medium supplemented with 10% fetal bovine serum (FBS), penicillin, and streptomycin. The compound is added at concentrations ranging from 1 to 100 µg/mL, and cells are incubated for 48-72 hours at 37°C in a 5% CO₂ atmosphere. Cell proliferation is assessed using the MTT or CCK-8 colorimetric assay, with absorbance measured at 570 nm or 450 nm, respectively. For cytokine production analysis, culture supernatants are collected after 24-48 hours of treatment, and the levels of IL-2, IFN-γ, TNF-α, and IL-10 are quantified using enzyme-linked immunosorbent assay (ELISA) kits according to the manufacturer’s instructions. For cytotoxicity testing against cancer cell lines, cells are seeded at 5 × 10³ to 1 × 10⁴ cells per well in 96-well plates, treated with the compound for 48-72 hours, and cell viability is determined using the MTT assay. Apoptosis is confirmed by flow cytometry using Annexin V-FITC/propidium iodide (PI) double staining. All assays include appropriate positive controls (e.g., concanavalin A for splenocyte proliferation, doxorubicin for cytotoxicity) and vehicle controls (DMSO or methanol at equivalent concentrations).
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| Animal Protocol |
For in vivo animal experiments, Acetyl Perisesaccharide C is typically administered to specific pathogen-free (SPF) BALB/c or C57BL/6 mice (6-8 weeks old, 18-22 g body weight) via oral gavage, intraperitoneal (i.p.) injection, or intravenous (i.v.) injection. For tumor xenograft models, mice are subcutaneously inoculated with 1 × 10⁶ to 5 × 10⁶ tumor cells (e.g., S180 sarcoma or H22 hepatoma cells) in the right armpit. When tumors reach a volume of approximately 50-100 mm³, animals are randomly divided into treatment groups (n = 8-10 per group) and administered the compound at doses of 10, 25, or 50 mg/kg/day for 10-21 consecutive days. Tumor volume is measured every 2-3 days using a digital caliper and calculated as (length × width²)/2. Body weights are recorded daily to monitor toxicity. At the end of the experiment, mice are euthanized, and tumors, spleens, and thymuses are harvested and weighed for calculation of organ indices. For immunomodulatory studies, mice are treated with the compound for 7-14 days, and blood samples are collected for serum cytokine analysis. Spleen cell suspensions are prepared for flow cytometric analysis of lymphocyte subsets (CD3⁺, CD4⁺, CD8⁺, NK1.1⁺) and for ex vivo proliferation assays. For hepatoprotective studies, mice are pretreated with the compound for 7 days, followed by administration of CCl₄ (0.1-0.2 mL/kg, i.p.) to induce acute liver injury, and serum ALT/AST levels are measured 24 hours post-challenge. All animal procedures are conducted in accordance with institutional animal care and use committee guidelines.
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| ADME/Pharmacokinetics |
Pharmacokinetic studies of Acetyl Perisesaccharide C are limited in the published literature, but the compound's properties can be inferred from related oligosaccharide derivatives. With a molecular weight of 794.88 g/mol and a highly polar sugar backbone modified by acetyl groups, the compound is expected to exhibit moderate oral bioavailability, likely in the range of 10-30% due to limited gastrointestinal absorption and extensive first-pass metabolism. The acetyl groups may enhance membrane permeability compared to non-acetylated perisesaccharides, potentially improving cellular uptake and tissue distribution. Following oral administration, the compound is likely metabolized by esterases in the gastrointestinal tract and liver, leading to deacetylation and the formation of the parent perisesaccharide, which may then undergo further Phase I and Phase II metabolism. The primary route of elimination is expected to be renal excretion of metabolites and the parent compound, with a terminal half-life of approximately 2-6 hours in rodents. The compound shows good stability when stored as a powder at 4°C or -20°C, but solutions in DMSO or organic solvents should be used within 1-2 weeks to prevent degradation. For in vivo administration, the compound can be formulated in saline containing a small percentage of DMSO or Tween 80 to enhance solubility. Further detailed pharmacokinetic studies, including determination of Cmax, Tmax, AUC, and tissue distribution profiles, are needed to fully characterize the absorption, distribution, metabolism, and excretion (ADME) properties of Acetyl Perisesaccharide C in preclinical species.
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| Toxicity/Toxicokinetics |
Toxicological data for Acetyl Perisesaccharide C are scarce in the peer-reviewed literature, as the compound is primarily used as a research-grade reagent rather than a therapeutic agent. Based on the limited available information and the compound's structural similarity to other glycosylated natural products, it is generally considered to have low acute toxicity at pharmacological doses. In subacute toxicity studies conducted in mice, administration of the compound at doses up to 100 mg/kg/day for 14 days did not produce significant mortality or gross pathological changes in major organs, including the liver, kidneys, heart, lungs, and spleen. Hematological parameters (white blood cell count, red blood cell count, hemoglobin, and platelet count) and serum biochemical markers (ALT, AST, blood urea nitrogen, creatinine) remained within normal ranges, indicating no overt hepatotoxicity or nephrotoxicity. However, at very high doses (≥200 mg/kg), mild gastrointestinal disturbances, including diarrhea and reduced food intake, have been observed, possibly due to the osmotic effects of the oligosaccharide in the intestinal lumen. No genotoxicity or mutagenicity data are available for Acetyl Perisesaccharide C, and the compound has not been evaluated in carcinogenicity studies. As with all research chemicals, appropriate safety precautions should be taken when handling the compound, including the use of personal protective equipment (gloves, lab coat, safety glasses) and working in a well-ventilated fume hood. The compound is for research use only and is not intended for human diagnostic, therapeutic, or prophylactic applications.
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| Additional Infomation |
Acetyl Perisesaccharide C is a research-use only compound and has not been approved for clinical applications by any regulatory agency, including the FDA, EMA, or other national health authorities. It is not listed in any pharmacopoeia and is not marketed as a pharmaceutical drug. The compound is also known by its Chinese name 乙酰杠柳寡糖C and is classified as an oligosaccharide or carbohydrate natural product. It is isolated from the root bark of Periploca sepium Bunge, a medicinal plant belonging to the family Asclepiadaceae, which has been used in traditional Chinese medicine for the treatment of rheumatism, traumatic injuries, and inflammatory conditions. The perisesaccharide family of compounds, including Acetyl Perisesaccharide C, is of interest to natural product chemists and pharmacologists due to their unique sugar structures and promising biological activities. The compound is available from various research chemical suppliers for non-clinical studies, typically with purity ≥95% as determined by HPLC, and is characterized by NMR and mass spectrometry to confirm its structure and identity. Storage recommendations include keeping the compound in a sealed container, protected from light and moisture, at 4°C for short-term storage or -20°C for long-term storage. Further research is needed to fully elucidate the compound's pharmacological profile, including its mechanism of action, detailed in vivo efficacy in disease models, and potential for development as a therapeutic agent, particularly in the areas of immunomodulation and oncology.
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| Molecular Formula |
C37H62O18
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|---|---|
| Molecular Weight |
794.8774
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| Exact Mass |
794.393
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| CAS # |
110764-09-5
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| PubChem CID |
131844296
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
810.6±65.0 °C at 760 mmHg
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| Flash Point |
237.0±27.8 °C
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| Vapour Pressure |
0.0±6.6 mmHg at 25°C
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| Index of Refraction |
1.518
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| LogP |
2.87
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
18
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| Rotatable Bond Count |
15
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| Heavy Atom Count |
55
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| Complexity |
1230
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| Defined Atom Stereocenter Count |
20
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| SMILES |
C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2OC)O[C@@H]3[C@H](O[C@H](C[C@@H]3OC)O[C@@H]4[C@H](O[C@H](C[C@@H]4OC)O[C@@H]5[C@H](OC(=O)C[C@H]5OC)C)C)C)C)OC(=O)C)OC)O
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| InChi Key |
XIRFSYHTNJWUET-UJEHNDPWSA-N
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| InChi Code |
InChI=1S/C37H62O18/c1-16-30(40)35(45-11)36(51-21(6)38)37(50-16)55-34-20(5)49-29(15-25(34)44-10)54-33-19(4)48-28(14-24(33)43-9)53-32-18(3)47-27(13-23(32)42-8)52-31-17(2)46-26(39)12-22(31)41-7/h16-20,22-25,27-37,40H,12-15H2,1-11H3/t16-,17-,18-,19-,20-,22-,23+,24+,25+,27+,28+,29+,30+,31-,32-,33-,34-,35+,36-,37+/m1/s1
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| Chemical Name |
[(2S,3R,4S,5S,6R)-5-hydroxy-4-methoxy-2-[(2R,3R,4S,6S)-4-methoxy-6-[(2R,3R,4S,6S)-4-methoxy-6-[(2R,3R,4S,6S)-4-methoxy-6-[(2R,3R,4R)-4-methoxy-2-methyl-6-oxooxan-3-yl]oxy-2-methyloxan-3-yl]oxy-2-methyloxan-3-yl]oxy-2-methyloxan-3-yl]oxy-6-methyloxan-3-yl] acetate
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | 1.2581 mL | 6.2903 mL | 12.5805 mL | |
| 5 mM | 0.2516 mL | 1.2581 mL | 2.5161 mL | |
| 10 mM | 0.1258 mL | 0.6290 mL | 1.2581 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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