An ansamycin antibiotic and antifungal
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Ansatrienin B

Item No. 21996

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(cyclohexylcarbonyl)-D-alanine, (5R,6E,8E,10E,13S,14R,15R,16Z)-15,22,24-trihydroxy-5-methoxy-14,16-dimethyl-3-oxo-2-azabicyclo[18.3.1]tetracosa-1(24),6,8,10,16,20,22-heptaen-13-yl ester
CAS Number
82189-04-6
Synonyms
  • Mycotrienin II
  • SDZ-115 962
Molecular Formula
C36H50N2O8
Formula Weight
638.8
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C(N[C@H](C)C(O[C@H]([C@H](C)[C@@H](O)/C(C)=C\CCC1=CC(O)=CC(N2)=C1O)C/C=C/C=C/C=C/[C@H](OC)CC2=O)=O)C3CCCCC3
InChi Code
InChI=1S/C36H50N2O8/c1-23-14-13-17-27-20-28(39)21-30(34(27)42)38-32(40)22-29(45-4)18-11-6-5-7-12-19-31(24(2)33(23)41)46-36(44)25(3)37-35(43)26-15-9-8-10-16-26/h5-7,11-12,14,18,20-21,24-26,29,31,33,39,41-42H,8-10,13,15-17,19,22H2,1-4H3,(H,37,43)(H,38,40)/b6-5+,12-7+,18-11+,23-14-/t24-,25+,29-,31-,33-/m0/s1
InChi Key
VVJDHJZQBGWPEQ-UOZMSBJPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Ansatrienin B is an ansamycin antibiotic and antifungal agent first isolated from S. collinus and S. rishiriensis.1,2 In fetal rat long bones, it is an inhibitor of parathyroid hormone-induced calcium release (IC50 = 21 nM), which is a measure of bone resorption, and pp60c-src kinase (IC50 = 50 nM).3 It is an inhibitor of translation at the protein synthesis stage by specific inhibition of L-leucine incorporation (IC50 = 58 nM in A549 cells).4 It also inhibits TNF-α-induced expression of intercellular adhesion molecule-1 (ICAM-1; IC50 = 300 nM). Early in vitro studies showed that ansatrienin B potentiates the chemotherapeutic action of 5-fluorouracil (Item No. 14416), cisplatin (Item No. 13119), bleomycin (Item No. 13877), mitomycin C (Item No. 11435), and 6-mercaptopurine.5 Ansatrienin B is a hydroquinone form of ansatrienin A (Item No. 21995).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Damberg, M., Russ, P., and Zeeck, A. Die konstitution der fungistatischen ansamycin-antibiotica ansatrienin A und B. Tetrahedron Lett. 23(1), 59-62 (1982).

    2. Sugita, M., Natori, Y., Sasaki, T., et al. Studies on mycotrienin antibiotics, a novel class of ansamycins. I. Taxonomy, fermentation, isolation and properties of mycotrienins I and II. J. Antibiot. (Tokyo) 35(11), 1460-1466 (1982).

    3. Feuerbach, D., Waelchli, R., Fehr, T., et al. Mycotrienins. A new class of potent inhibitors of osteoclastic bone resorption. The Journal of Biological Chemisty 270(43), 25949-25955 (1995).

    4. Yamada, Y., Tashiro, E., Taketani, S., et al. Mycotrienin II, a translation inhibitor that prevents ICAM-1 expression induced by pro-inflammatory cytokines. J. Antibiot. (Tokyo) 64(5), 361-366 (2011).

    5. Kuwano, M., Ikezaki, K., Mamizuka, K., et al. Potentiation of mitomycin C, 6-mercaptopurine, bleomycin, cis-diamminedichloroplatinum and 5-fluorouracil by mycotrienins and mycotrienols. Gan. 74(5), 759-766 (1983).