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Ansamitocin P-3 (Synonyms: Antibiotic C-15003P3, Maytansinol butyrate)

Catalog No.GC11947

A microtubule depolymerizing agent

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Ansamitocin P-3 Chemical Structure

Cas No.: 66547-09-9

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10mM (in 1mL DMSO)
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5mg
$81.00
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10mg
$135.00
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25mg
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50mg
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Sample solution is provided at 25 µL, 10mM.

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Quality Control & SDS

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Protocol

Cell experiment:

MCF-7, EMT-6/AR1, HeLa and MDA-MB-231 cells are seeded in 96 well plates. Subsequently, cells are incubated with vehicle (0.1% DMSO) or different concentrations (1-1000 pM) of Ansamitocin P3 for 48 h in MCF-7 cells and 24 h for EMT-6/AR1, HeLa and MDA-MB-231 cells, respectively. The half maximal inhibitory concentration of cell proliferation (IC50) for Ansamitocin P3 is determined by sulforhodamine B assay. Four independent experiments are carried out in MCF-7 cells and three independent sets of experiments are performed in EMT-6/AR1, HeLa and MDA-MB-231 cells[2].

References:

[1]. Kiso T, 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. 2004 May;48(5):1739-48
[2]. Venghateri JB, et al. Ansamitocin P3 depolymerizes microtubules and induces apoptosis by binding to tubulin at thevinblastine site. PLoS One. 2013 Oct 4;8(10):e75182.

Background

Ansamitocin P-3, a natural product, is maytansinoid which showed potent cytotoxicity against the human solid tumor cell lines A-549 and HT-29 with ED50 of 4 x 10 -7, 4 x 10 – 7 μg/ml, respectively. [1]
Cytotoxic agents remain an important strategy in chemotherapy. In an activity-directed isolation and identification, ansamitocin P-3 was obtained from the active methanol extracts of two mosses.
Furthermore, the compound showed great cytotoxicity against several tumor cells. [1]
Ansamitocin P-3 is a maytansinoid isolated in very low yield from two members of the moss family Thuidiaceae, Claopodium crispifolium (Hook.) Ren. & Card. and Anomodon attenuatus (Hedw.) Hueb. Further biological evaluation of ansainitocin P-3 showed potent cytotoxicity against the human solid tumor cell line systems A-549 lung carcinoma cells, HT-29 colon adenocarcinoma cells and MCF-7 breast adenocarcinoma cells at ED50 of 4 x 10 -7, 4 x 10 - 7, 2 x 10 -6 μg/ml. respectively. [2]
Ansamitocin P-3 exhibited inhibition of cilia regeneration of partially deciliated Tetrahymena. The regeneration of cilia in Tetrahymena was assayed by observing recovery of motility of the deciliated cells which are nonmotile after being deciliated. After 60 min of incubation, more than 95% of partially deciliated Tetrahymena cells in the recovery buffer were fully motile. Ansamitocin P-3 completely inhibited cilia regeneration of Tetrahymena at 1 μM. Moreover, recovery of motility of partially deciliated cells after release from inhibition by 2 μM ansamitocin P-3. [2]
References:
[1]. Suwanborirux, K., et al. "Ansamitocin P-3, a maytansinoid, fromClaopodium crispifolium andAnomodon attenuatus or associated actinomycetes."Experientia 46.1 (1990): 117-120.
[2]. Tanida, Seiichi, Eiji Higashide, and Masahiko Yoneda. "Inhibition of cilia regeneration of Tetrahymena by ansamitocins, new antitumor antibiotics."Antimicrobial agents and chemotherapy 16.1 (1979): 101.

Chemical Properties

Cas No. 66547-09-9 SDF
Synonyms Antibiotic C-15003P3, Maytansinol butyrate
Canonical SMILES CCCC(O[C@@]([C@]1([C@@](O1)([H])[C@]([C@](O2)([H])C[C@](N=C2O)(O)[C@@](OC)([H])/C([H])=C([H])/C([H])=C(CC3=CC(N4C)=C(Cl)C(OC)=C3)\C)([H])C)C)([H])CC4=O)=O
Formula C32H43ClN2O9 M.Wt 635.14
Solubility ≥ 31.75 mg/mL in DMSO, ≥ 33.73 mg/mL in EtOH with ultrasonic and warming Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 1.5745 mL 7.8723 mL 15.7446 mL
5 mM 0.3149 mL 1.5745 mL 3.1489 mL
10 mM 0.1574 mL 0.7872 mL 1.5745 mL
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