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    Pirarubicin (THP)
    Pirarubicin (THP)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1419
    CAS #: 72496-41-4Purity ≥98%

    Description: Pirarubicin (THP; THPADM; THPDOX; 1609RB; THP-Adriamycin; THP-Doxorubicin; Pinorubicin; Theprubicine; Therarubicin) is an analog of anthracycline with potential antitumor activity. It acts as a topoisomerase II inhibitor, and has been used for treatment of various cancers.

    References: Jpn J Cancer Res. 1999 Jul;90(7):775-80; Chemotherapy. 2010;56(2):101-7. 

    Related CAS No.95343-20-7 (HCl); 72496-41-4 (free base)

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    Molecular Weight (MW)627.64 
    CAS No.72496-41-4 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 7 mg/mL (11.2 mM) 
    Water: <1 mg/mL
    Ethanol: <1 mg/mL
    Other info

    Chemical Name: (8S,10S)-10-(((2R,4S,5S,6S)-4-amino-6-methyl-5-(((S)-tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione


    InChi Code: InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21-,22-,31+,32-/m0/s1

    SMILES Code: O=C1C2=C(O)C(C[[email protected]](C(CO)=O)(O)C[[email protected]@H]3O[[email protected]]4C[[email protected]](N)[[email protected]](O[[email protected]]5CCCCO5)[[email protected]](C)O4)=C3C(O)=C2C(C6=C1C=CC=C6OC)=O


    THP; THPADM; THPDOX; 1609RB; Tepirubicin; Tetrahydropyranyl-Doxorubicin; THP-Adriamycin; THP-Doxorubicin. brand names: Pinorubicin; Theprubicine; Therarubicin. 

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    In Vitro

    In vitro activity: Pirarubicin is rapidly taken up by M5076 cells and the intracellular concentration of pirarubicin reaches more than 2.5-fold that of doxorubicin. Pirarubicin is more effective than doxorubicin in terms of the 50% cell growth-inhibitory concentration in vitro. Pirarubicin causes G0/G1 cell cycle arrest in MG-63 cells. Pirarubicin suppresses the expression of PCNA, cyclin D1, cyclin E and Bcl-2, and increases Bax expression in MG-63 cells. Pirarubicin markedly relaxes contractions induced by noradrenaline (0.1 μM) in the aorta with endothelium, but not in that without endothelium. Pirarubicin-induced relaxation is inhibited by methylene blue (5 μM), hydroquinone (100 μM), phenidone (50 μM), haemoglobin (1 μM) and p-bromophenacyl bromide (50 μM), but not by indomethacin (25 μM). Pirarubicin is approximately 2-5 times more potent than Adriamycin in SKUT1B, HEC1A, and BG1 cell lines. Pirarubicin also displays a reverse dose-response pattern of G2 block so that at high dose, cell cycle kinetics would mirror those of untreated controls.

    Cell Assay: MTS is used to analyze cell survival. Briefly, cells are plated in 96-well plates in triplicate at 2 × 103 cells per well and cultured in growth medium. Then cells are treated with pirarubicin at different concentrations (2.5 μg/mL, 5 μg/mL, 10 μg/mL) for 24 h. MTS reagent (5 mg/mL) is added and incubated at 37°C for 4 h. The absorbance is monitored at 490 nm using a microplate reader.

    In VivoPirarubicin reduces the tumor weight to 60% of the control level in M5076 solid tumor-bearing mice, although doxorubicin has no effect. Pirarubicin and Epirubicin are effective against V x 2 tumor when injected via the hepatic intra-arterial (h.i.a.) route, the activity of Pirarubicin is stronger than that of Epirubicin.
    Animal modelMice
    Formulation & DosageHepatic intra-arterial (h.i.a.) route

    Jpn J Cancer Res. 1999 Jul;90(7):775-80; Chemotherapy. 2010;56(2):101-7.  

    These protocols are for reference only. InvivoChem does not independently validate these methods.


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