epipodophyllotoxin
Epipodophyllotoxin is a natural product isolated from the rhizomes of the plant Podophyllum peltatum (Mayapple). It exhibits potent anti-cancer activity by inhibiting topoisomerase II, an enzyme essential for DNA replication and repair. Its mechanism of action involves trapping the enzyme in a DNA-cleaved complex, preventing further DNA replication and ultimately leading to cell death. Epipodophyllotoxin is the precursor for the semi-synthetic drugs etoposide and teniposide, which are used clinically to treat various cancers, including lung cancer, testicular cancer, and leukemia. The study of epipodophyllotoxin and its derivatives has been instrumental in understanding the role of topoisomerase II in cancer cell growth and proliferation, leading to the development of several anti-cancer agents. Furthermore, ongoing research focuses on the development of new epipodophyllotoxin analogs with enhanced efficacy and reduced side effects, aiming to improve cancer treatment outcomes.'
Cross-References
ID Source | ID |
---|---|
PubMed CID | 105111 |
CHEMBL ID | 282256 |
SCHEMBL ID | 5792464 |
MeSH ID | M0017088 |
Synonyms (20)
Synonym |
---|
brn 0099162 |
furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5r-(5-alpha,5a-beta,8a-alpha,9-beta))- |
furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5r,5ar,8ar,9s)- |
epipodophyllotoxin |
CHEMBL282256 |
(5s,5ar,8ar,9r)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one |
4375-07-9 |
SCHEMBL5792464 |
(10r,11r,15r,16s)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1(9),2,7-trien-12-one |
(-)-epipodophyllotoxin |
Q3589174 |
MS-27170 |
(5r)-5beta-(3,4,5-trimethoxyphenyl)-7alpha-(hydroxymethyl)-8alpha-hydroxy-5,6,7,8-tetrahydronaphtho[2,3-d]-1,3-dioxole-6beta-carboxylic acid 6,7-lactone |
furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5ah)-one,5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-,(5r,5ar,8ar,9s)- |
E80546 |
DTXSID10859440 |
(10r,11r,15r,16s)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one |
EN300-20599945 |
CS-0134999 |
HY-N7654 |
Bioassays (15)
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID398417 | Cytotoxicity against human HT-29 cells | 1995 | Journal of natural products, Jun, Volume: 58, Issue:6 | Methyl ethers of podophyllotoxin-related cyclolignans. |
AID83615 | In vitro cytotoxicity against the HT-29 (human colon carcinoma) neoplastic cell line | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and cytotoxicity of hydrophobic esters of podophyllotoxins. |
AID699782 | Growth inhibition of human HT-29 cells after 72 hrs by SRB assay | 2012 | Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15 | Synthesis and antimitotic and tubulin interaction profiles of novel pinacol derivatives of podophyllotoxins. |
AID398415 | Cytotoxicity against mouse P388 cells | 1995 | Journal of natural products, Jun, Volume: 58, Issue:6 | Methyl ethers of podophyllotoxin-related cyclolignans. |
AID404065 | Antiviral activity against HSV1 infected in human primary amnion cells assessed as inhibition of virus-induced pathogenic effect | 1998 | Journal of natural products, Nov, Volume: 61, Issue:11 | Antiviral activity of lignans. |
AID403984 | Therapeutic index, ratio of MTC for human primary amnion cells to lowest drug level causing inhibition of HSV1 | 1998 | Journal of natural products, Nov, Volume: 61, Issue:11 | Antiviral activity of lignans. |
AID404066 | Cytotoxicity against human primary amnion cells assessed as morphological changes by microscopic examination | 1998 | Journal of natural products, Nov, Volume: 61, Issue:11 | Antiviral activity of lignans. |
AID398416 | Cytotoxicity against human A549 cells | 1995 | Journal of natural products, Jun, Volume: 58, Issue:6 | Methyl ethers of podophyllotoxin-related cyclolignans. |
AID221407 | Compound was tested for Immunosuppression activity by mixed lymphocyte reaction (MLR) in murine splenocytes of mice | 1996 | Journal of medicinal chemistry, Jul-05, Volume: 39, Issue:14 | Immunosuppressive cyclolignans. |
AID140793 | Compound was tested for Cytotoxic activity by lymphocyte viability assay. | 1996 | Journal of medicinal chemistry, Jul-05, Volume: 39, Issue:14 | Immunosuppressive cyclolignans. |
AID152273 | In vitro cytotoxicity against the P-388 (from DBA/2 mouse) neoplastic cell line | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and cytotoxicity of hydrophobic esters of podophyllotoxins. |
AID235867 | Non cytotoxic IM activity index which is the ratio of IC50 of LcV to IC50 of MLR | 1996 | Journal of medicinal chemistry, Jul-05, Volume: 39, Issue:14 | Immunosuppressive cyclolignans. |
AID699781 | Growth inhibition of human A549 cells after 72 hrs by SRB assay | 2012 | Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15 | Synthesis and antimitotic and tubulin interaction profiles of novel pinacol derivatives of podophyllotoxins. |
AID9039 | In vitro cytotoxicity against the A-549 (human lung carcinoma) neoplastic cell line | 2004 | Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5 | Synthesis and cytotoxicity of hydrophobic esters of podophyllotoxins. |
AID1123832 | Inhibition of chicken brain microtubule polymerization after 30 mins | 1979 | Journal of medicinal chemistry, Mar, Volume: 22, Issue:3 | Conformational analysis of podophyllotoxin and its congeners. Structure--activity relationship in microtubule assembly. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (6)
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 1 (16.67) | 18.7374 |
1990's | 3 (50.00) | 18.2507 |
2000's | 1 (16.67) | 29.6817 |
2010's | 1 (16.67) | 24.3611 |
2020's | 0 (0.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Market Indicators
Research Demand Index: 43.28
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.
| This Compound (43.28) All Compounds (24.57) |
Study Types
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 1 (16.67%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 5 (83.33%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |