Ansamitocin P-3，AP3 CAS NO.66584-72-3

CAS number :66584-72-3
English name :ansamitocinP-3
English alias :Maytansinolisobutyrate; Tam-330; Tam330; Nsc292222; MTA/CBR32; ANSAMITOCINP-3; AnsamitosinP3; AnasamitocinP-3; US-DMFNo.:034434; AnsamitocinP-3,>98%
Chinese name: Anthricin P3 Chinese alias: Anthricin; Chemicalbook P3; Maidenol isobutyrate; Ansamicin AP3; Ansamectin P-3; Anthricin P3; Anthricin P-3(AP3); Ansicin P-3? , > 98%; MICROTUBULE inhibitor (ANSAMITOCINP-3); ANSAMITOCINP-3(MAYTANSINOLISOBUTYRATE)
CBNumber:CB42130228
Molecular formula :C32H43ClN2O9
Molecular weight :635.14
MOLFile:66584-72-3.mol
Chemical properties of ansicin P3
Melting point :190-192℃
Boiling point :833.1±65.0°C(Predicted)
Density :1.29
Storage conditions: Keepindarkplace, Inertatmosphere Storeinfreezer, under - 20 ° C
Solubility: DMChemicalbookSO: 100 mg/mL (157.45 mM); Ethanol: 55 mg/mL (86.60 mM)
Acidity coefficient (pKa):9.82±0.70(Predicted)
Form :Solid
Color :WhitetoOff-White
Water:Insoluble

Properties, uses and production technology of anthricin P3
use
AnsamitocinP-3 (AP3) is a small fraction of Ansa antibiotics, which has many pharmacological activities such as anti-tumor, anti-tuberculosis bacillus and anti-bacteria. Its components are P-0, P-1, P-2, P-3, P-3', P-4 and P-4', among which ansicin P-3 is the main synthetic product, which prevents cell death by preventing microtubule formation, and has significant anti-tumor effects in vitro and in tumor-bearing animals.
Method 1: A method for extraction, separation and purification of anthricin P-3, the method includes the following steps: 1) the fermentation liquid or solid fermentation medium at the end of the fermentation is extracted with an extraction solvent to obtain the extraction liquid; 2) Concentrate the extraction liquid obtained in step 1 until no extraction solvent flows out to get concentrated extract crude A, then add neutral alumina, and mix it evenly with crude A with organic solvent; 3) Steam the evenly mixed coarse product A of step 2 until it is dry and sandy; 4) Add the organic solvent to the dry sandy coarse product A in step 3, leave it in shock and take the supernatant; 5) Concentrate the supernatant of step 4, add silica gel and spin steam to sand, then gradient elution by column chromatography to obtain ansicin P-3.
Bioactive Ansamitocinp - 3 (Maytansinolisobutyrate NSC292222, AntibioticC15003P3) is a kind of effective tubulin polymerization inhibitor, IC50 of 3.4 microns.
Target the Maytansinoids
In vitro study
5μMAnsamitocinp-3 completely inhibited the polymerization of bovine brain-isolated microtubules, but compared with VCR,Ansamitocinp-3 did not cause tubulin polymerization at a high concentration of 80μM. 16μMAnsamitocinp-3 also effectively depolymerized microchemicalbook tubulin (IC50=3.8μM). The addition of Ansamitocinp-3 to cultured cells prevented a certain concentration of dibutyl cyclic adenosine 3':5' -phosphate from transforming AC cells from fibroepithelioid to gliomatoid cells. In addition, 16nMAnsamitocinp-3 treatment also led to rapid dispersion of the well-functioning cytoplasmic network of A31 cells. Ansamitocinp-3 briefly treated A31 cells or KB cells and also inhibited DNA synthesis. These results suggest that Ansamitocinp-3 acts by interacting with the microtubule assembly system, resulting in inhibition of mitotic spindle fiber formation and ultimately cell death.
Ansamitocinp-3 acts on A-549,HT-29, and MCF-7 cells, and this effect is dose-dependent, ED50 of 4×10 AnsamitocinP-3 acts on HCT-116 cells, and it is also toxic, EC50 is 0.081nM. Ansamitocinp-3 enhances the effect of radiation on fruit fly cells and human cancer cells in a p53-dependent manner.
In vivo study
Ansamitocinp-3(>1µg) significantly inhibited the growth of leukemia SN36 and induced P388 leukemia cells to stop in the middle of cell division. Ansamitocinp-3 was treated at a dose of 25µg/kg daily in mice with intraperitoneally injected B16 malignant melanoma, significantly extending lifespan by 130%. Ansamitocinp-3 treatment also significantly extended the lifespan of mice carrying Ehrlich ascites carcinoma,Sarcoma180, and P815 mastocytoma, but only marginally extended the lifespan of mice carrying ascites MOPC-104E myeloma, leukemia L1210, and leukemia C1498.

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