Cytochalasin B - Moligand™, ≥98% , CAS No.14930-96-2

CAS: 14930-96-2 Cat. No.: C113160 Molecular Weight: 479.61 Beilstein Registry Number: 1096207 EC Number: 239-000-2

GRADE & PURITY Moligand™, ≥98%

Synonyms

C19954 | IDI1_034070 | MLS002703001 | SCHEMBL9046718 | 2H-Oxacyclotetradec(2,3-d)isoindole-2,18(5H)-dione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-, (E,E)-(5S,9R,12aS,13S,15S,15aS,16S,18aS)- | BDBM

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Cytochalasin B is used in actin polymerization studies and cytological research. Cytochalasin B is a metabolite of the fungus Drechslera dematoidea which binds to the barbed end of actin filaments resulting in inhibition of both the association and dissociation of subunits. As opposed to other Cytochalasins, cytochalasin A and Cytochalasin B bind to the glucose transporter and inhibit monosaccharide transport across the plasma membrane. Cytochalasin B inhibits phagocytosis by both mononuclear phagocytes and polymorphonuclear leukocytes
A cell-permeable fungal toxin used in actin polymerization studies and cytological

Specifications

Synonyms

C19954 | IDI1_034070 | MLS002703001 | SCHEMBL9046718 | 2H-Oxacyclotetradec(2, 3-d)isoindole-2, 18(5H)-dione, 16-benzyl-6, 7, 8, 9, 10, 12a, 13, 14, 15, 15a, 16, 17-dodecahydro-5, 13-dihydroxy-9, 15-dimethyl-14-methylene-, (E, E)-(5S, 9R, 12aS, 13S, 15S, 15aS, 16S, 18aS)- | BDBM

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

One of a group of fungal metabolites that interfere with a wide variety of cellular movements. Useful tool for characterizing some of the polymerization properties of actin, and in studies on cytokinesis. Probe for the two hexose-transport systems in rat

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1CCCC(C=CC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O)O
• IUPAC Name: (1S,4E,6R,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione
• InChIKey: GBOGMAARMMDZGR-TYHYBEHESA-N
• INCHI: 1S/C29H37NO5/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/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1
• Isomeric SMILES: C[C@@H]1CCC[C@H](/C=C/C(=O)O[C@]23[C@@H](/C=C/C1)[C@@H](C(=C)[C@H]([C@H]2[C@@H](NC3=O)CC4=CC=CC=C4)C)O)O
• WGK Germany: 3
• RTECS: RO0205000
• UN Number: 1544
• Molecular Weight: 479.61
• Beilstein: 1096207
• Reaxy-Rn: 949535
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=949535&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Cytochalasans
      • Subclass Cytochalasins

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Cytochalasans
• Subclass: Cytochalasins
• Intermediate Tree Nodes: Not available
• Direct Parent: Cytochalasins
• Alternative Parents: Isoindolones Isoindoles Benzene and substituted derivatives Pyrrolidine-2-ones Enoate esters Secondary carboxylic acid amides Cyclic alcohols and derivatives Secondary alcohols Lactams Lactones Oxacyclic compounds Azacyclic compounds Monocarboxylic acids and derivatives Organopnictogen compounds Hydrocarbon derivatives Carbonyl compounds Organic oxides Organonitrogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Lactone cytochalasin skeleton - Cytochalasin - Isoindolone - Isoindoline - Isoindole - Isoindole or derivatives - Monocyclic benzene moiety - Pyrrolidone - Benzenoid - 2-pyrrolidone - Cyclic alcohol - Pyrrolidine - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Secondary carboxylic acid amide - Secondary alcohol - Carboxamide group - Carboxylic acid ester - Lactam - Lactone - Organoheterocyclic compound - Carboxylic acid derivative - Oxacycle - Azacycle - Monocarboxylic acid or derivatives - Organopnictogen compound - Organic oxygen compound - Alcohol - Organonitrogen compound - Carbonyl group - Organic oxide - Hydrocarbon derivative - Organic nitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cytochalasins. These are cytochalasans in which the hydrogenated isoindolone bears a benzyl group.
• External Descriptors: Cytochalasins

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MAOA Tclin Monoamine oxidase A (11911 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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MAOB Tclin Monoamine oxidase B (8835 Activities)

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ITGAL Tclin Leukocyte adhesion glycoprotein LFA-1 alpha (170 Activities)

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SLC2A1 Tchem Glucose transporter (14755 Activities)

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A498 (42825 Activities)

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HL-60 (67320 Activities)

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MCF7 (126967 Activities)

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SK-MEL-2 (46422 Activities)

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SK-OV-3 (52876 Activities)

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XF498 (12972 Activities)

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A549 (127892 Activities)

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HCT-116 (91556 Activities)

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HepG2 (196354 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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HCT-15 (51914 Activities)

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SLC2A3 Tchem Solute carrier family 2, facilitated glucose transporter member 3 (465 Activities)

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SLC2A2 Tchem Solute carrier family 2, facilitated glucose transporter member 2 (428 Activities)

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SLC2A4 Tchem Solute carrier family 2, facilitated glucose transporter member 4 (396 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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NPC1 Tchem Niemann-Pick C1 protein (18985 Activities)

Discover Target: NPC1

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RAB9A Tbio Ras-related protein Rab-9A (22488 Activities)

Discover Target: RAB9A

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BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)

Discover Target: BAZ2B

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ITGAL Tclin Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 (760 Activities)

Discover Target: ITGAL

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Associated Targets(non-human)

Mapk1 MAP kinase ERK2 (650 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Vibrio parahaemolyticus (473 Activities)

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CHO (4503 Activities)

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RAW264.7 (28094 Activities)

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Vero (26788 Activities)

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C6 (2371 Activities)

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H4 (48 Activities)

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BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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TGR Thioredoxin glutathione reductase (28579 Activities)

Discover Target: TGR

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Cirsium arvense (30 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in methanol (20 mg/ml), and 1:20 DMF:PBS(7.2) (~0.05 mg/ml).
• Sensitivity: Heat sensitive;Light sensitive;Moisture sensitive
• Melt Point(°C): 218-223°C
• Molecular Weight: 479.600 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 479.267 Da
• Monoisotopic Mass: 479.267 Da
• Topological Polar Surface Area: 95.900 Ų
• Heavy Atom Count: 35
• Formal Charge: 0
• Complexity: 859.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

References

1. Yaqi Feng, Mi Li.  (2023)  Micropipette-assisted atomic force microscopy for single-cell 3D manipulations and nanomechanical measurements.  Nanoscale,      [PMID:37526589] [10.1039/D3NR02404K]

2. Yuying Bai, Dawei Tian, Zhengxin Ren, Dangyang Yue, Qian Ren, Li Pei, Jun Pan.  (2023)  The dependences of mesenchymal stem cells commitments on the size, concentration, internalization and exposure time of Iron Oxide Nanoparticles through F-actin, Lamin A and ROS.  JOURNAL OF BIOMEDICAL MATERIALS RESEARCH PART A,      [PMID:36939155] [10.1002/jbm.a.37534]

3. Xinyue Li, Yuanyuan Fan, Zhengbao Zha, Deyan Gong, Jiajia Yu, Qianhui Li, Ruoyao Li, Hua Wang, Fei Wang.  (2023)  Cordycepin-Loaded Macrophage Vesicles for Targeted Nonalcoholic Steatohepatitis Attenuation.  ADVANCED FUNCTIONAL MATERIALS,  33  (18): (2214059).  [PMID:] [10.1002/adfm.202214059]

4. Sun Xiaoxi, Huang Bing, Pan Yuping, Fang Jinhua, Wang Hefeng, Ji Yanru, Ling Yingchen, Guo Pei, Lin Jiangguo, Li Quhuan, Fang Ying, Wu Jianhua.  (2022)  Spatiotemporal characteristics of P-selectin-induced β2 integrin activation of human neutrophils under flow.  Frontiers in Immunology,      [PMID:36439190] [10.3389/fimmu.2022.1023865]

5. Luchun Zhang, Meng Yuan, Xingwei Huang, Qianzi Cao, Shaogang Huang, Ruizhen Sun, Lei Lei.  (2022)  Inhibition of METTL5 improves preimplantation development of mouse somatic cell nuclear transfer embryos.  REPRODUCTION,      [PMID:36111643] [10.1530/REP-22-0169]

6. Zhe Chen, Qing Luo, Chuanchuan Lin, Dongdong Kuang, Guanbin Song.  (2016)  Simulated microgravity inhibits osteogenic differentiation of mesenchymal stem cells via depolymerizing F-actin to impede TAZ nuclear translocation..  Scientific Reports,      [PMID:27444891] [10.1038/srep30322]

7. Gu Haiping, Lou Jun, Wang Haizhen, Yang Yu, Wu Laosheng, Wu Jianjun, Xu Jianming.  (2016)  Biodegradation, Biosorption of Phenanthrene and Its Trans-Membrane Transport by Massilia sp. WF1 and Phanerochaete chrysosporium.  Frontiers in Microbiology,      [PMID:26858710] [10.3389/fmicb.2016.00038]

8. Y.N. Lin, R. Jia, Y.H. Liu, Y. Gao, L.L. Wang, J.P. Kou, B.Y. Yu.  (2015)  Ruscogenin suppresses mouse neutrophil activation: Involvement of protein kinase A pathway.  JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY,      [PMID:26134424] [10.1016/j.jsbmb.2015.06.003]

9. Jiaqi Lin, Ziwei Lin, Anqi Huang, Xinyi Wu, Wei Yan, Daojun Liu, Chiju Wei, Wencan Xu.  (2025)  Effects of a PDGF-Stem Cell-Hydrogel Compound on Skin Wound Healing in Mice.  CYTOTHERAPY,      [PMID:40121568] [10.1016/j.jcyt.2025.01.001]

10. Di Wu, Hang Sun, Bingwei Yang, Erqun Song, Yang Song, Weihong Tan.  (2024)  Exosome Heterogeneity Affects the Distal “Barrier-Crossing” Trafficking of Exosome Encapsulated Quantum Dots.  ACS Nano,      [PMID:38394382] [10.1021/acsnano.3c09378]

11. Yijie Li, Shuni Duan, Yinhao Zhang, Runping Liu, Rong Sun, Jianzhi Wu, Zhi Ma, Xiaojiaoyang Li.  (2025)  Precise subcellular organelle-targeted analyses of hepatotoxicity of Polygonum multiflorum.  Chinese Herbal Medicines,      [PMID:41584695] [10.1016/j.chmed.2025.03.001]

12. Zixuan Dong, Song Liu, Xiaobing Liu, Dong He, Qi Chu, Linjie Zhong, Xiangyu Yu, Xiaoling Fu.  (2025)  Therapeutic Mitochondrial Transfer via Mesenchymal Stem Cell-Derived Microvesicles for Macrophage Modulation in Myocardial Infarction Complicated by Diabetes.  BIOMATERIALS,      [PMID:40706127] [10.1016/j.biomaterials.2025.123563]

13. Zixuan Dong, Xiaobing Liu, Shichun Li, Xiaoling Fu.  (2025)  Inhibition and Rescue of Hyperglycemia-Induced Cellular Senescence by Mitochondrial Transfer from Enucleated Mesenchymal Stem Cell-Derived Microvesicles for Chronic Wound Healing.  Advanced Science,      [PMID:40407245] [10.1002/advs.202501612]