A microtubule depolymerizing agent
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Ansamitocin P-3

Item No. 20538

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-O-de[2-(acetylmethylamino)-1-oxopropyl]-3-O-(1-oxobutyl)-maytansine
CAS Number
66547-09-9
Synonyms
  • Antibiotic C-15003P3
  • Maytansinol butyrate
Molecular Formula
C32H43ClN2O9
Formula Weight
635.2
Purity
≥85%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS(pH7.2) (1:2): 0.33 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/ml
λmax
232, 251, 280 nm
SMILES
C[C@@]1([C@@H](O1)[C@H](C)[C@]([H])(C[C@](N2)(O)[C@]([H])(OC)/C=C/C=C(CC3=CC(OC)=C(Cl)C4=C3)\C)OC2=O)[C@@]([H])(OC(CCC)=O)CC(N4C)=O
InChi Code
InChI=1S/C32H43ClN2O9/c1-8-10-27(37)43-25-16-26(36)35(5)21-14-20(15-22(40-6)28(21)33)13-18(2)11-9-12-24(41-7)32(39)17-23(42-30(38)34-32)19(3)29-31(25,4)44-29/h9,11-12,14-15,19,23-25,29,39H,8,10,13,16-17H2,1-7H3,(H,34,38)/b12-9+,18-11+/t19-,23+,24-,25
InChi Key
WLKHTIAFMSHJLG-BYXOJEECSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    10 mg

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    25 mg

    $736

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    Cayman Chemical
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    Product Description

    Ansamitocin P-3 is a microtubule depolymerizing agent that can be isolated from culture broths of certain Gram-positive bacteria.1,2 It binds tubulin (Kd = 1.3 µM), depolymerizes microtubules in both interphase and mitosis, and perturbs chromosome segregation.3 Ansamitocin P-3 also activates the spindle checkpoint surveillance proteins Mad2 and BubR1, blocking cell cycling during mitosis.3 It inhibits the growth of cancer cells in culture and significantly suppresses the growth of several cancer tumors in mice, prolonging survival time.1,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ootsu, K., Kozai, Y., Takeuchi, M., et al. Effects of new antimitotic antibiotics, ansamitocins, on the growth of murine tumors in vivo and on the assembly of microtubules in vitro. Cancer Res. 40(5), 1707-1717 (1980).

    2. Kiso, T., Fujita, J.-I., Ping, X., et al. Screening for microtubule-disrupting antifungal agents by using a mitotic-arrest mutant of Aspergillus nidulans and novel action of phenylalanine derivatives accompanying tubulin loss. Antimicrob. Agents Chemother. 48(5), 1739-1748 (2004).

    3. Venghateri, J.B., Gupta, T.K., Verma, P.J., et al. Ansamitocin P3 depolymerizes microtubules and induces apoptosis by binding to tubulin at the vinblastine site. PLoS One 8(10), (2013).