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| Targets |
The molecular target of Neocryptomerin appears to be associated with the inhibition of topoisomerase II, an enzyme crucial for DNA replication and cell division. By inhibiting this enzyme, Neocryptomerin can induce DNA damage and trigger cell cycle arrest, leading to the death of rapidly proliferating cells. Additionally, it has been shown through computational docking studies to have favorable binding affinities in the active pocket of the SARS-CoV-2 main protease (Mpro), suggesting a potential mechanism for its antiviral activity. However, as a natural product, it may have multiple targets, and its primary protein target remains an active area of investigation. Its phenolic hydroxyl groups are likely involved in its interaction with cellular proteins.
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| ln Vitro |
In vitro studies have shown that Neocryptomerin possesses broad-spectrum anticancer activity. Specifically, it has demonstrated inhibitory activity against several human cancer cell lines, including the human glioblastoma cell line U251 (IC50 in the low micromolar range), the human breast cancer cell line MCF-7, and the human cervical cancer cell line HeLa. The compound also exhibited cytotoxic effects against other cell lines, such as A549 (lung cancer) and HepG2 (liver cancer). The in vitro activity is typically assessed using MTT or SRB assays after 48-72 hours of treatment. Its activity is concentration-dependent, and the observed potency is consistent with other natural product biflavonoids that act through topoisomerase inhibition and apoptosis induction.
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| ln Vivo |
In vivo data for Neocryptomerin is very limited, as it remains in the early stages of preclinical research. Most studies have been confined to in vitro cell-based assays. There is no published in vivo animal model efficacy data specifically for Neocryptomerin against tumor xenografts or in viral infection models. However, given its structural similarity to other bioactive biflavonoids (e.g., amentoflavone) that show in vivo antitumor and anti-inflammatory activity, it is plausible that Neocryptomerin would exhibit similar pharmacokinetic and pharmacodynamic properties. Further studies are required to establish its bioavailability, in vivo efficacy, and safety profile in animal models. Currently, its use is strictly limited to in vitro experiments and structural characterization studies.
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| Enzyme Assay |
No specific in vitro enzyme or receptor binding assays have been standardized and published for Neocryptomerin. However, the methodology to assess its binding to SARS-CoV-2 Mpro is based on computational molecular docking. For this, the 3D structure of the target protein (e.g., PDB: 6LU7) is obtained from the Protein Data Bank. The compound's 3D structure is prepared and minimized. AutoDock Vina or Schrödinger Maestro software is then used to predict the binding pose and calculate the binding free energy (deltaG) or docking score. Hydrogen bonds and hydrophobic interactions with key active site residues (e.g., Cys145, His41) are analyzed. To confirm topoisomerase II inhibition, a DNA relaxation assay is performed, where purified topoisomerase II and DNA are incubated with the compound, and DNA relaxation is visualized by agarose gel electrophoresis. The compound's purity (≥98%) is confirmed by HPLC.
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| Cell Assay |
In vitro cellular assays are the standard method for testing Neocryptomerin's activity. Human cancer cell lines (U251, MCF-7, HeLa, A549, etc.) are cultured in appropriate media (e.g., DMEM or RPMI-1640) supplemented with 10% fetal bovine serum (FBS) and 1% penicillin-streptomycin. Cells are seeded in 96-well plates at a density of 5,000-10,000 cells per well and allowed to attach overnight. The cells are then treated with varying concentrations (e.g., 0-100 microM) of Neocryptomerin for 48 or 72 hours, with a final DMSO concentration not exceeding 0.1%. Cell viability is then measured using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) or SRB (Sulforhodamine B) colorimetric assay. The absorbance is read at 570 nm (for MTT) or 510 nm (for SRB) using a microplate reader. The half-maximal inhibitory concentration (IC50) is calculated using GraphPad Prism. For apoptosis detection, an Annexin V-FITC/PI double staining kit is used, followed by flow cytometry.
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| Animal Protocol |
No standardized in vivo animal protocols exist for Neocryptomerin in public scientific literature, as the compound has not yet advanced to animal studies. To conduct such a study, a murine xenograft model would be typical. Immunodeficient nude mice would be inoculated subcutaneously with 5×10⁶ U251 or MCF-7 cells. Once tumors reach 100-150 mm3, mice would be randomized into groups (n=8-10). Neocryptomerin would be formulated in a vehicle such as a saline solution containing up to 10% DMSO and 10% Tween 80. The compound would be administered via intraperitoneal (IP) or intravenous (IV) injection daily or every other day. Tumor volume would be measured with calipers, and body weight recorded. At study termination, tumors would be excised and analyzed by histology (H&E) and immunohistochemistry (e.g., Ki-67 for proliferation, cleaved caspase-3 for apoptosis). The effective dose (ED50) and maximum tolerated dose (MTD) would be determined. However, these are proposed methods, not published data.
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| ADME/Pharmacokinetics |
No published data on the pharmacokinetics (PK) of Neocryptomerin is available. As a biflavonoid with a molecular weight of 552.48 g/mol and a relatively high LogP value of 5.856, the compound is likely highly lipophilic, which may result in poor aqueous solubility and low oral bioavailability. This class of compounds typically has limited absorption and extensive first-pass metabolism. The compound is likely to be metabolized by phase II conjugation enzymes (glucuronidation, sulfation). The plasma protein binding is expected to be high due to its multiple phenolic groups and lipophilic nature. Without dedicated studies, the volume of distribution, half-life, and clearance remain unknown. Solubility data suggests it is soluble in DMSO but may have low solubility in physiological buffers; thus, formulations for in vivo use would require optimization (e.g., use of cyclodextrins, liposomes, or nanoemulsions). The in vitro solubility is often enhanced with DMSO, but the concentration for in vivo use is limited by the toxicity of the vehicle. Storage at -20degC under inert conditions is recommended.
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| Toxicity/Toxicokinetics |
No specific toxicology studies have been published for Neocryptomerin. However, due to its structural similarity to other biflavonoids, it may exhibit dose-dependent hepatotoxicity, as many polyphenolic compounds can cause liver damage at high doses. The compound has an aromatic structure and multiple phenolic groups, which can undergo redox cycling and generate reactive oxygen species (ROS), leading to oxidative stress and cellular damage. It should be regarded as a potential skin and respiratory irritant. Standard safety precautions for handling bioactive natural products should be employed, including the use of gloves, safety glasses, and working in a fume hood. As it is a research-grade product with demonstrated cell growth inhibitory activity, it is assumed to be cytotoxic and should be handled with appropriate care. It is not intended for human use as a therapeutic.
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| References | |
| Additional Infomation |
Reports indicate that Podocarpus macrophyllus contains cryptosporin, and relevant data is available for reference.
Neocryptomerin is a biflavonoid isolated from several plant species, including Cryptomeria japonica (Japanese cedar) and Selaginella tamariscina (a spikemoss). Biflavonoids are a subclass of flavonoids characterized by the dimerization of two flavonoid units. This compound has garnered interest for its potential therapeutic applications in both cancer and viral infections. Computational studies have suggested that Neocryptomerin has favorable binding affinities in the active pocket of the SARS-CoV-2 main protease, indicating a potential as a lead compound against COVID-19. However, these are preliminary computational findings and require extensive experimental validation. The compound is used solely as a research tool for investigating the biological activities of natural products and is not approved for any clinical use. Its natural abundance is low, so it is typically obtained through chemical synthesis or advanced extraction and purification processes for research purposes. The product is supplied for research use only, not for human use. |
| Molecular Formula |
C31H20O10
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|---|---|
| Molecular Weight |
552.48
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| Exact Mass |
552.106
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| CAS # |
20931-36-6
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| PubChem CID |
5320065
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| Appearance |
Off-white to light yellow solid powder
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| LogP |
5.856
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
41
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| Complexity |
1040
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC1=CC(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)OC4=C(C5=C(C=C4O)OC(=CC5=O)C6=CC=C(C=C6)O)O)O
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| InChi Key |
YEMFTKDEHYFESW-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C31H20O10/c1-38-19-10-20(33)28-21(34)12-24(40-26(28)11-19)16-4-8-18(9-5-16)39-31-23(36)14-27-29(30(31)37)22(35)13-25(41-27)15-2-6-17(32)7-3-15/h2-14,32-33,36-37H,1H3
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| Chemical Name |
5,7-dihydroxy-6-[4-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)phenoxy]-2-(4-hydroxyphenyl)chromen-4-one
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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) |
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 | 1.8100 mL | 9.0501 mL | 18.1002 mL | |
| 5 mM | 0.3620 mL | 1.8100 mL | 3.6200 mL | |
| 10 mM | 0.1810 mL | 0.9050 mL | 1.8100 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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