Molecular Formula | C32H37NO12
|
Molar Mass | 627.64 |
Density | 1.51±0.1 g/cm3(Predicted) |
Melting Point | 188-192°C (dec.) |
Boling Point | 834.7±65.0 °C(Predicted) |
Specific Rotation(α) | D25 +175 ±25° (c = 0.2 in CHCl3) |
Flash Point | 458.6°C |
Solubility | ethanol: soluble25mg/mL |
Vapor Presure | 1.51E-29mmHg at 25°C |
Appearance | powder |
Color | Orange to Red |
pKa | 7.35±0.60(Predicted) |
Storage Condition | 2-8°C |
Stability | Hygroscopic |
Refractive Index | 1.67 |
Physical and Chemical Properties | Red solid, melting point 188~192 C (decomposition). [Α] D23 175 ° ± 25 °(C = 0.2, chloroform). UV and visible absorption maxima (methanol):234,252,290,498,531.5,580nm(E1 cm1h0, 350,110,140,100,45). Soluble in ethyl acetate, chloroform or ethanol, slightly soluble in water, hexane or petroleum ether. Acute toxicity LD50 mice (mg/kg):27.8 I. V. |
Use | Pirarubicin is an anthracycline. |
In vitro study | Pirarubicin was rapidly taken up by M5076 cells and reached an intracellular concentration of over 2.5 times that of doxorubicin. Pirarubicin was more effective than doxorubicin in inhibiting 50% of cell growth in vitro. In MG-63 cells, Pirarubicin causes cell cycle arrest at the G0/ G1 phase. In MG-63 cells, Pirarubicin inhibited the expression of PCNA, cyclin D1,cyclin E and Bcl-2, and increased Bax protein expression. In MG-63 cells, Pirarubicin markedly relaxed noradrenaline (0.1 μm)-induced contraction of the endothelial aorta, but had no effect on cells without endothelium. Pirarubicin-induced relaxation was induced by methylene blue (5 μm), hydroquinone (100 μm), phenidone (50 μm), hemoglobin (1 μm) and p-bromobenzoylmethyl bromide (50 μm) but not by indomethacin (25 μm). In SKUT1B,HEC1A and BG1 cell lines, Pirarubicin is about 2-5 times more potent than adriacin. Pirarubicin also showed a reverse dose-response pattern of G2 hindrance, such that at high doses, cell cycle dynamics would mimic those of untreated controls. |
In vivo study | In mice with M5076 solid tumors, Pirarubicin reduced tumor weight to 60% of control levels, although doxorubicin had no effect. When Pirarubicin and Epirubicin are injected via the hepatic intra-arterial (HIA) route, effective against V × 2 tumors, Pirarubicin is more active than Epirubicin. |