Physicochemical Properties
| Molecular Formula | C30H39NO5 |
| Exact Mass | 493.283 |
| CAS # | 53760-19-3 |
| PubChem CID | 5351303 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.19g/cm3 |
| Boiling Point | 676.5ºC at 760mmHg |
| Melting Point | 252-258ºC |
| Flash Point | 362.9ºC |
| Index of Refraction | 1.591 |
| LogP | 4.066 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 36 |
| Complexity | 920 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CC1C/C=C\C2C(C(=C)C(C3C2(C(/C=C/C(C1)(C)O)OC(=O)C)C(=O)NC3Cc4ccccc4)C)O |
| InChi Key | NAEWXXDGBKTIMN-BBXOWAOSSA-N |
| InChi Code | InChI=1S/C30H39NO5/c1-18-10-9-13-23-27(33)20(3)19(2)26-24(16-22-11-7-6-8-12-22)31-28(34)30(23,26)25(36-21(4)32)14-15-29(5,35)17-18/h6-9,11-15,18-19,23-27,33,35H,3,10,16-17H2,1-2,4-5H3,(H,31,34)/b13-9+,15-14+ |
| Chemical Name | [(3E,9E)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-18-oxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| ln Vitro | Cytochalasin H (24–72 h) suppresses the growth of A549 cells with an IC50 value of 159.5 µM[1]. A549 cells undergo apoptosis when exposed to cytochalasin H (0–50 µM; 48 h), which also stops the cell cycle in the G2/M phase and modifies the expression of proteins linked to apoptosis [1]. Antibacterial activity of cytochalasin H (1-512 μg/mL) is demonstrated against Staphylococcus aureus, Gram-positive bacteria, and MDR enteric pathogens [3]. |
| ln Vivo | In Balb/cnu/nu mice, cytochalasin H (2.5 mg/kg; ip) slows the growth of A549 xenograft tumors [2]. |
| Cell Assay |
Apoptosis Analysis[1] Cell Types: A549 cells Tested Concentrations: 0, 6.25, 12.5, 25 and 50 µM Incubation Duration: 48 h Experimental Results: Induced apoptosis in a dose-dependent manner in the A549 cells. Cell Cycle Analysis[1] Cell Types: A549 cells Tested Concentrations: 0, 6.25, 12.5, 25 and 50 µM Incubation Duration: 48 h Experimental Results: Arrested cell cycle at the G2 /M phase and sub-G1 peaks. Western Blot Analysis[1] Cell Types: A549 cells Tested Concentrations: 0, 6.25, 12.5, 25 and 50 µM Incubation Duration: 48 h Experimental Results: Increased the protein expression levels of Bax, P53 and cleaved caspase-3 and diminished the protein expression levels of Bcl-xL, Bcl-2 and full-length caspase-3. |
| Animal Protocol |
Animal/Disease Models: male Balb/cnu/nu (nude) mice with A549 xenograft[2] Doses: 2.5 mg/kg Route of Administration: intraperitoneal (ip)injection; 3 injections/week,for 80 days Experimental Results: Attenuated tumor growth in vivo. |
| References |
[1]. Cytochalasin H isolated from mangrove‑derived endophytic fungus induces apoptosis and inhibits migration in lung cancer cells. Oncol Rep. 2018 Jun;39(6):2899-2905. [2]. In Vivo Anti-tumor Effects of the Ethanol Extract of Gleditsia sinensis Thorns and Its Active Constituent, Cytochalasin H. Biol Pharm Bull. 2015;38(6):909-12. [3]. Antibacterial and cytotoxic cytochalasins from the endophytic fungus Phomopsis sp. harbored in Garcinia kola (Heckel) nut. BMC Complement Altern Med. 2016 Nov 14;16(1):462. |
| Additional Infomation | Cytochalasins are mycotoxins that have the ability to bind to actin filaments and block polymerization and the elongation of actin. As a result, they can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. Cytochalasins also have the ability to permeate cell membranes, prevent cellular translocation, cause cells to enucleate, and affect other aspects of biological processes unrelated to actin polymerization. Cytochalasin H is has been isolated from the fungus Phomopsis paspali. It also regulates plant growth and has shown CNS activity. (A2910, A2911, L1913, L1916) |
Solubility Data
| 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 |
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |