Cytochalasin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-01754 |
| CAS | 14110-64-6 |
| Molecular Weight | 477.59 |
| Molecular Formula | C29H35NO5 |
| Purity | >98% by HPLC |
Online Inquiry
Description
It is produced by the strain of Helminthosporium dematioideum, Coriolus vernicipes. It has many biological activities, such as inhibiting cytokinesis reversibly, inhibiting megasophil endocytosis and exocytosis. Cytochalasin A is an HIV protease inhibitor.
Specification
| Synonyms | NSC174119; Dehydrophomin; 5-Dehydrophomin; 5,5-Didehydrophomin; 2H-Oxacyclotetradecino(2,3-d)isoindole-2,5,18-trione, 6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-13-hydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-, (3E,9R,11E,12aS,13S,15S,15aS,16S,18aS)-; (7S,13E,16R,21E)-7-Hydroxy-16-methyl-10-phenyl-24-Oxa[14]cytochalasa-6(12),13,21-triene-1,20,23-trione; 16-Benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-13-hydroxy-9,15-dimethyl-14-methylene-2H-Oxacyclotetradecino[2,3-d]isoindole-2,5,18-trione |
| Storage | -20 °C |
| IUPAC Name | (1S,4E,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-15-hydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,6,21-trione |
| Canonical SMILES | CC1CCCC(=O)C=CC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O |
| InChI | InChI=1S/C29H35NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,23-24,26-27,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,23+,24+,26+,27-,29-/m1/s1 |
| InChI Key | ZMAODHOXRBLOQO-TZVKRXPSSA-N |
| Source | Cytochalasin A was first isolated in the fungus Helminthosporium dermatioideum. |
Properties
| Appearance | Off-White to White Solid |
| Boiling Point | 725.1 °C at 760 mmHg |
| Melting Point | 185-187 °C |
| Flash Point | 392.3±32.9 °C |
| Density | 1.20 g/cm3 |
| Solubility | Soluble in Acetone; Slightly soluble in DMSO, Methanol |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Cytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament. One cytochalasin will bind to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. Cytochalasin A also inhibits the transport of monosaccharides across the cell membrane. |
Reference Reading
1. Effect of Mycotoxin Cytochalasin A on Photosystem II in Ageratina adenophora
Zhi Luo, Shiguo Chen, Yanjing Guo, Qian Yang, He Wang, Jiale Shi, Xiaoxiong Wang, Sheng Qiang, Mengyun Jiang, Reto Jörg Strasser Plants (Basel) . 2022 Oct 21;11(20):2797. doi: 10.3390/plants11202797.
Biological herbicides have received much attention due to their abundant resources, low development cost, unique targets and environmental friendliness. This study reveals some interesting effects of mycotoxin cytochalasin A (CA) on photosystem II (PSII). Our results suggested that CA causes leaf lesions onAgeratina adenophoradue to its multiple effects on PSII. At a half-inhibitory concentration of 58.5 μΜ (I50, 58.5 μΜ), the rate of O2evolution of PSII was significantly inhibited by CA. This indicates that CA possesses excellent phytotoxicity and exhibits potential herbicidal activity. Based on the increase in the J-step of the chlorophyll fluorescence rise OJIP curve and the analysis of some JIP-test parameters, similar to the classical herbicide diuron, CA interrupted PSII electron transfer beyond QAat the acceptor side, leading to damage to the PSII antenna structure and inactivation of reaction centers. Molecular docking model of CA and D1 protein ofA. adenophorafurther suggests that CA directly targets the QBsite of D1 protein. The potential hydrogen bonds are formed between CA and residues D1-His215, D1-Ala263 and D1-Ser264, respectively. The binding of CA to residue D1-Ala263 is novel. Thus, CA is a new natural PSII inhibitor. These results clarify the mode of action of CA in photosynthesis, providing valuable information and potential implications for the design of novel bioherbicides.
2. Action of cytochalasin A, a sulfhydryl-reactive agent, on sugar metabolism and membrane-bound adenosine triphosphatase of yeast
S C Kuo, J O Lampen Biochim Biophys Acta . 1975 Apr 21;389(1):145-53. doi: 10.1016/0005-2736(75)90392-2.
Cytochalasin A at 10-20 mug/ml inhibits growth and sugar uptake by Saccharomyces strain 1016. The effects of cytochalasin A in intact cells were completely prevented when 1 mM cysteine or dithiothreitol was added along with cytochalasin A, but were not eliminated by thiols added after inhibition had occurred. Purified yeast hexokinase, glucose-6-P dehydrogenase, phosphofructokinase and aldolase were not sensitive to cytochalasin A (20 mug/ml). Glyceraldehyde-3-P dehydrogenase was strongly inhibited by cytochalasin A (5 mug/ml); activity was promptly restored by thiols. Anaerobic glycolysis was inhibited by cytochalasin A or by iodoacetate; unlike iodoacetate, cytochalasin A did not cause accumulation of sugar phosphates. In contrast, cytochalasin A, but not iodoacetate, inhibited isolated membrane-bound ATPases. Cytochalasin A is a sulfhydryl-reactive agent and has membrane-related effects (adenosine triphosphatase) which may well be the basis of its interference with energy-dependent uptake of solutes.
3. Cytochalasin A inhibits B-lymphocyte capping and activation by antigens
M F La Via, A Misefari, D Venza-Teti, G Teti Immunol Lett . 1981 Aug;3(3):151-4. doi: 10.1016/0165-2478(81)90118-8.
Cytochalasin B (CB) has been shown to be a potent depressant of the antigen-induced clone expansion and terminal differentiation of mouse B-lymphocytes to antibody-forming cells. This effect could be the result of the microfilament-disrupting effect of CB with subsequent inhibition of antigen-sIg complex redistribution, a series of events which seems to be necessary for B-lymphocyte activation. CB is not very active in depressing capping and will inhibit glucose transport. To further investigate the mechanism of action of cytochalasins, the effect of cytochalasin A (CA) on cap formation and plaque-forming cell generation was studied, since CA is less inhibitory of glucose transport and more inhibitory of cap formation. The results presented here indicate that complexes of anti-Ig-sIg will be prevented from capping by as little as 1 microgram of CA, a quantity sufficient to depress markedly the generation of plaque-forming cells to SRBC in culture. These results further confirm our conclusion that the depression of B-lymphocyte activation may be related to the depression of cap formation. It also strongly suggested that inhibition of glucose transport can be regraded as a negligible factor in this depression.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C29H35NO5
Molecular Weight (Monoisotopic Mass): 477.2515 Da
Molecular Weight (Avergae Mass): 477.5919 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C29H35NO5
Molecular Weight (Monoisotopic Mass): 477.2515 Da
Molecular Weight (Avergae Mass): 477.5919 Da
Recommended Products
| BBF-01825 | Loganin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
