Ansamitocin P-3 Has Anti-tumor and Antibacterial Activities

English name：ansamitocin P-3

CAS number：66584-72-3

The molecular formula: C32H43ClN2O9

Molecular weight 635.14EINECS No

Related categories:Cell biological reagents; antibiotics; biological fermentation; pharmaceutical raw materials; CellSignalingandNeuroscience; CyChemicalbooktoskeletonandExtracellularMatrix; MicrotobuleInhibitors

Mol document:66584-72-3.mol

Structural formula:

Anisisin P 3 properties

Melting point: 190-192℃

Boiling point: 833.1 ± 65.0 C (Predicted)

Density: 1.29

Storage conditions: Keepindarkplace, Inertatmosphere, Storeinfreezer, unChemicalbookder-20 C

Solubility: DMSO:100mg/mL(157.45mM); Ethanol: 55mg/mL(86.60mM)

Aciity coefficient: (pK a) 9.82 ± 0.70 (Predicted)

Form: solid

Color: White to a white type

Water solubility: Water: Insoluble

Use

Amisicin P-3 (AnsamitocinP-3, AP3) is a small molecule Ansa antibiotic with anti-tumor, anti-tuberculosis and anti-bacterial pharmacological activities; its components: P-0, P-1, P-2, PChemicalbook-3, P-3 ', P-4 and P-4'. Amisicin P-3 is the main synthetic product, which causes cell death by blocking microtubule formation, and has significant antitumor effect in vitro and tumor-bearing animals.

Preparation method

Method 1: A method for extraction and purification of Anisicin P-3 comprising the following steps:

1. The fermentation solution or solid fermentation medium is extracted with the extraction solvent to obtain the extraction solution;
2. Step 1) Concentrate the resulting extract to get the concentrated extract crude A, then add neutral alumina, and Chemicalbook use organic solvent to mix it evenly with crude A;
3. Step 2) Steam the evenly mixed rough product A to the dry sand shape;
4. Add the organic solvent to step 3) in the dried sand A, shock stand, take the supernatant;
5. The supernatant of step 4) was concentrated, steamed to sandy, and eluted by column chromatography to obtain anisectin P-3.

Biological activity

Ansamitocin p-3 (Maytansinol isobutyrate, NSC292222, Antibiotic C 15003P3) is a potent inhibitor of tubulin polymerization with a IC50 of 3.4 μ M.

Target spot

Maytansinoids

In vitro study

5 μMAnsamitocinp-3 completely inhibited microtubule polymerization isolated from cattle brains, but did not cause tubulin polymerization at a high Ansamitocinp-3 concentration of 80 μ M compared to VCR.16 μMAnsamitocinp-3 also effectively depolymerizes the aggregated tubulin (IC50=3.8 μ M). Addition of Ansamitocinp-3 to the cultured cells prevented a concentration of dibutyl-cyclic adenosine 3 ′: 5 ′ -phosphate changed the AC cell morphology from fibroepithelia-like to glioma-like cells. Moreover, 16nMAnsamitocinp-3 treatment also caused a rapid dispersion of the favorable cytoplasmic network of A31 cells. Short-term treatment of A31 cells or KB cells by AnsamitocinpChemicalbook-3 also inhibited DNA synthesis. These results suggest that Ansamitocinp-3 acts by interacting with the microtubule assembly system, leading to the inhibition of mitotic spindle fiber formation, ultimately leading to cell death. Ansamitocinp-3 is toxic on A-549, HT-29, and MCF-7 cells, this effect is dose-dependent, ED50410Ansamitocinp-3 on HCT-116 cells, also toxic with an EC50 of 0.081 nM. Effect of Ansamitocinp-3 in enhancing radiation effects in Drosophila cells and human cancer cells, in a p53-dependent manner.

In vivo research

Treatment with Ansamitocinp-3 (> 1 µ g) significantly inhibited leukemic SN 36 growth and induced P388 leukemic cell arrest during metaphase of cell division. Ansamitocinp-3 Treatment of mice carrying intraperitoneal injection of B16 malignant melanoma at a dose of 25 µ g / kg daily significantly increased life span with extended Chemicalbook of 130% longer. Ansamitocinp-3 treatment also significantly extended the lifespan of mice carrying Ehrlich ascites carcinoma, Sarcoma180, and P815 mastocytoma, but only weakly in mice carrying ascites MOPC-104E myeloma, leukemia L1210, and leukemia C1498.

Security information

dangerous mark:Xn

Hazard category code: 20 / 22-36 / 37 / 38

Safety instructions: 26-36

WGK Germany:3

RTECS number: OQ2293000

Customs code: 2941900000

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