A cytochalasin with diverse biological activities
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Deoxaphomin

Item No. 44753

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,3aR,4S,6S,6aR,7E,10R,14R,15E,17aR)-3,3a,4,5,6,6a,9,10,11,12, 13,14-dodecahydro-6,14-dihydroxy-4,10-dimethyl-5-methylene-3-(phenylmethyl)-1H-Ccclotridec[d]isoindole-1,17(2H)-dione
CAS Number
51053-39-5
Molecular Formula
C29H37NO4
Formula Weight
463.6
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
O=C1[C@]23[C@]([C@@H](C([C@H]([C@]2([H])/C=C/C[C@@H](CCC[C@H](/C=C/C3=O)O)C)O)=C)C)([H])[C@@H](N1)CC4=CC=CC=C4
InChi Code
InChI=1S/C29H37NO4/c1-18-9-7-13-22(31)15-16-25(32)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
InChi Key
GPCJCBIEJCXNKC-TYHYBEHESA-N
Origin
Fungus/Drechslera sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

    250 µg

    $139

    Add

    1 mg

    $528

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Deoxaphomin is a polyketide synthase-derived cytochalasin that has been found in P. semeniperda and has diverse biological activities.1,2,3,4 It inhibits anti-mouse IgG-induced capping in isolated mouse splenic lymphocytes by 70% when used at a concentration of 20 µM and inhibits actin filament elongation in C3H fibroblasts by 66% at 2 µM.3 Deoxaphomin (100 µM) inhibits seed germination and radicle growth induced by GR24 (Item No. 13210) in the broomrapes O. crenata and P. ramosa.2 It inhibits the growth of OE21, U373 MG, SK-MEL-28, A549, B16/F10, and Hs 683 cancer cells (IC50s = 0.75, 1.7, 5.9, 2.2, and 0.61 µM, respectively).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Steyn, P.S. The biosynthesis of polyketide-derived mycotoxins. J. Environ. Pathol. Toxicol. Oncol. 11(1), 47-59 (1992).

    2. Cimmino, A., Fernández-Aparicio, M., Andolfi, A., et al. Effect of fungal and plant metabolites on broomrapes (Orobanche and Phelipanche spp.) seed germination and radicle growth. J. Agric. Food Chem. 62(43), 10485-10492 (2014).

    3. Yahara, I., Harada, F., Sekita, S., et al. Correlation between effects of 24 different cytochalasins on cellular structures and cellular events and those on actin in vitro. J. Cell Biol. 92(1), 69-78 (1982).

    4. Van Goietsenoven, G., Mathieu, V., Andolfi, A., et al. In vitro growth inhibitory effects of cytochalasins and derivatives in cancer cells. Planta Med. 77(7), 711-717 (2011).