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    Podophyllotoxin
    Information
    CAS No. 518-28-5 Price $30 / 20mg
    Catalog No.CFN99168Purity>=98%
    Molecular Weight414.41Type of CompoundLignans
    FormulaC22H22O8Physical DescriptionPowder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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    Biological Activity
    Description: Podophyllotoxin(Podofilox ) is a potent inhibitor of microtubule assembly and DNA topoisomerase II. Podophyllotoxin has antitumor and antiviral properties, but it also shows cytotoxicity for normal cells and hence side effects derived from its lack of selectivity against tumoral cells.
    Targets: Topoisomerase | MMP(e.g.TIMP)
    In vitro:
    Anticancer Agents Med Chem. 2014 Nov 30.
    Recent Developments Towards Podophyllotoxin Congeners as Potential Apoptosis Inducers.[Pubmed: 25469512]
    Podophyllotoxin, a lignan extracted from rhizomes of Podophyllum species, is a well established lead in the development of new chemical agents for the treatment of cancer. Its semi-synthetic variant, etoposide is an anticancer drug which inhibits DNA topoisomerase II causing cell cycle arrest in the S the phase. Its clinical success and intriguing mode of action made it a much sought after skeleton for the development of better antitumor agents. Modifications were made at several positions of its skeleton with the aim to either improve its potency or to overcome drug resistance. In recent years, the structurally modified Podophyllotoxins have been investigated for their apoptosis inducing ability. Although numerous reviews emphasized the occurrence, synthesis and applications of Podophyllotoxins, the recent progress towards development of structurally modified Podophyllotoxins possessing apoptosis inducing ability has not been previously reviewed.
    CONCLUSIONS:
    Therefore the present review focuses on the studies carried out in the design and synthesis of new Podophyllotoxin derivatives and their evaluation as apoptosis inducers.
    Exp Ther Med. 2014 May;7(5):1317-1322. Epub 2014 Mar 6.
    Apoptosis of human gastric cancer SGC-7901 cells induced by podophyllotoxin.[Pubmed: 24940431]
    Numerous studies have demonstrated that Podophyllotoxin and its derivatives exhibit antitumor effects. The aim of the present study was to investigate SGC-7901 cell apoptosis and the underlying mechanism induced by Podophyllotoxin. SGC-7901 cells were treated with varying concentrations of Podophyllotoxin.
    METHODS AND RESULTS:
    MTT assays and flow cytometry were used to evaluate the effects of Podophyllotoxin on the proliferation and apoptosis of SGC-7901 cells, while fluorescence inverted microscopy was used to observe the morphology of SGC-7901 cells that had been dyed with Hoechst 33258. In addition, laser scanning confocal microscopy was used to analyze the mitochondrial membrane potential (MMP) of SGC-7901 cells dyed with Rhodamine 123. Western blotting was performed to analyze the expression levels of cytochrome c (cyt-c), caspase-9 and caspase-3 in the SGC-7901 cells. The results indicated that Podophyllotoxin was capable of inhibiting growth and inducing the apoptosis of SGC-7901 cells in a dose-dependent manner, causing cell cycle arrest at the G2/M phase. After 48 h of treatment, the apoptotic morphology of SGC-7901 cells was clear, exhibiting cell protuberance, concentrated cytoplasms and apoptotic bodies. Following 24 h of treatment, the MMP of the SGC-7901 cells decreased. In addition, after 48 h, the expression of cyt-c was shown to be upregulated, while the expression levels of pro-caspase-9 and pro-caspase-3 in the SGC-7901 cells were shown to be downregulated.
    CONCLUSIONS:
    In conclusion, apoptosis can be induced in SGC-7901 cells by Podophyllotoxin, potentially via a mitochondrial pathway, indicating that Podophyllotoxin may be a potent agent for cancer treatment.
    Podophyllotoxin Description
    Source: The roots of Dysosma versipellis (Hance) M.Cheng ex Ying.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 2.4131 mL 12.0653 mL 24.1307 mL 48.2614 mL 60.3267 mL
    5 mM 0.4826 mL 2.4131 mL 4.8261 mL 9.6523 mL 12.0653 mL
    10 mM 0.2413 mL 1.2065 mL 2.4131 mL 4.8261 mL 6.0327 mL
    50 mM 0.0483 mL 0.2413 mL 0.4826 mL 0.9652 mL 1.2065 mL
    100 mM 0.0241 mL 0.1207 mL 0.2413 mL 0.4826 mL 0.6033 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Structure Identification:
    Curr Pharm Des. 2000 Dec;6(18):1811-39.
    Antitumor properties of podophyllotoxin and related compounds.[Pubmed: 11102564]
    The lignan family of natural products includes compounds with important antineoplastic and antiviral properties such as Podophyllotoxin and two of their semisynthetic derivatives, etoposide and teniposide. The latter are included in a wide variety of cancer chemotherapy protocols. Due to these biological activities, lignans, and especially cyclolignans, have been the objective of numerous studies focused to prepare better and safer anticancer drugs. The mechanism by which Podophyllotoxin blocks cell division is related to its inhibition of microtubule assembly in the mitotic apparatus. However, etoposide and teniposide were shown not to be inhibitors of microtubule assembly which suggested that their antitumor properties were due to another mechanism of action, via their interaction with DNA and inhibition of DNA topoisomerase II.
    METHODS AND RESULTS:
    Other Podophyllotoxin derivatives has also been reported which retained or even improved the cytotoxic activity, but these were weak inhibitors of topoisomerase II in vitro; the data revealed that such analogs exhibit a different, as yet unknown, mechanism of action. The main deficiency of these compounds is their cytotoxicity for normal cells and hence side effects derived from their lack of selectivity against tumoral cells. In this regard it is necessary to investigate and prepare new more potent and less toxic analogs, that is, with better therapeutic indices. It is well accepted from structure-activity studies in this field that the trans-lactones are more potent as antineoplastics than the cis-lactones. Not only the configuration of the D ring is an important factor for high cytotoxic activity, but also a quasi-axial arrangement of the E ring is necessary. On this basis, studies on lignans have been addressed to modify the lactone moiety and prepare analogs with heteroatoms at different positions of the cyclolignan skeleton. Our group has been working during the last few years on chemical transformations of Podophyllotoxin and analogs and we have prepared a large number of cyclolignan derivatives some of which display potent antiviral, immunosuppressive and cytotoxic activities. We have reported several new cytotoxic agents with nitrogen atoms at C-7 or C-9 or at both C-7 and C-9: imine derivatives, oxime derivatives, pyrazoline-, pyrazo- and isoxazoline-fused cyclolignans.
    CONCLUSIONS:
    At present, we are preparing mainly new compounds by modifications of the A and E cyclolignan-rings. They are being tested on cultures of different tumoral cell lines (P-388 murine leukemia, A-549 human lung carcinoma, HT-29 human colon carcinoma and MEL-28 human melanoma) and some of them have shown an interesting and selective cytotoxicity.