An actin depolymerizing macrolide
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16-epi Latrunculin B

Item No. 19608

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4S)-4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-2-thiazolidinone
CAS Number
444911-05-1
Molecular Formula
C20H29NO5S
Formula Weight
395.5
Purity
≥95%
Formulation (Request formulation change)
A film
Solubility(Learn about Variance in Solubility)
DMSO: solubleEthanol: soluble
SMILES
C/C(CC/C=C\[C@H]1C)=C/C(O[C@H]2C[C@@]([C@]3([H])NC(SC3)=O)(O)O[C@H](CC1)C2)=O
InChi Code
InChI=1S/C20H29NO5S/c1-13-5-3-4-6-14(2)9-18(22)25-16-10-15(8-7-13)26-20(24,11-16)17-12-27-19(23)21-17/h3,5,9,13,15-17,24H,4,6-8,10-12H2,1-2H3,(H,21,23)/b5-3-,14-9-/t13-,15-,16-,17-,20-/m1/s1
InChi Key
NSHPHXHGRHSMIK-WAXGXQFOSA-N
Origin
Sponge/Negombata magnifica
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 µg

    $156

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    Product Description

    16-epi Latrunculin B, first isolated from the Red Sea sponge N. magnifica, is a stereoisomer of the actin polymerization inhibitor, latrunculin B (Item No. 10010631).1,2 At 5-10 µg/ml, 16-epi latrunculin B can disrupt microfilament activity in an actin disruption assay.2 It also demonstrates cytotoxic activity in mouse KA31T and NIH3T3 tumor cells (GI50s = 1 and 4 µg/ml, respectively) and antiviral activity against herpes simplex type 1 virus (ED50 = 1 µg/ml).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hoye, T.R., Ayyad, S.E.N., Eklov, B.M., et al. Toward computing relative configurations: 16-epi-latrunculin B, a new stereoisomer of the actin polymerization inhibitor latrunculin B. J. Am. Chem. Soc. 124(25), 7405-7410 (2016).

    2. Vilozny, B., Amagata, T., Mooberry, S.L., et al. A new dimension to the biosynthetic products isolated from the sponge Negombata magnifica. J. Nat. Prod. 67(6), 1055-1057 (2004).