Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H20O8 |
| Molecular Weight | 400.3787 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12COC(=O)[C@]1([H])[C@H](C3=CC(OC)=C(O)C(OC)=C3)C4=C(C=C5OCOC5=C4)[C@H]2O
InChI
InChIKey=YVCVYCSAAZQOJI-JHQYFNNDSA-N
InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1
4'-demethylepipodophyllotoxin (DMEP) belongs to the class of podophyllotoxin. Podophyllotoxin is a natural product from the roots and rhizomes
of Podophyllum species and binds at the colchicine site as a microtubule inhibitor. DMEP is an antimitotic agent which binds to monomeric tubulin, preventing microtubule polymerization. It can reduce the tumor formation and growth in a mouse skin carcinogenesis model. DMEP derivatives exert strong antitumor properties.
Approval Year
Sample Use Guides
The backs of the animals were shaved 2 days prior to the start of the experiment. The animals were divided into three groups (n = 10 for each group). Group I animals served as controls. These animals received acetone (200 μl/mouse) application only. Group II animals received two topical applications of 0.24% 9, 10-dimethylbenz[a]anthracene (DMBA) in acetone (200 μl/mouse) over a period of 1 week, followed by 5 nmol 12-O-tetradecanoylphorbol-13-acetate (TPA) in acetone (50 μl/mouse) twice weekly for 24 weeks. The mice of group III were treated as Group II mice, except that they were treated with 4'-demethylepipodophyllotoxin (DMEP) (200 μl of the solution in acetone at a concentration of 1 μg/ml), 30 min prior to application of the above dose of TPA twice weekly for 24 weeks.
Route of Administration:
Transdermal
In Vitro Use Guide
Curator's Comment: Treatment of Chinese hamster cells with 4'-demethylepipodophyllotoxin caused a dose-dependent increase in the mitotic index.
https://www.ncbi.nlm.nih.gov/pubmed/8517914
4'-demethylepipodophyllotoxin (DMEP) showed cytotoxicity activity against five human tumor cell lines (i.e., BGC-823, KB, HepG2, K-562, and HL-60) and a normal human cell line (i.e., HK-2) The EC50s of DMEP against these tumor cell lines ranged from 0.31 to 398 uM.
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DTXSID7048742
Created by
admin on Sat Dec 16 09:53:58 GMT 2023 , Edited by admin on Sat Dec 16 09:53:58 GMT 2023
|
PRIMARY | |||
|
X0S6I23X6L
Created by
admin on Sat Dec 16 09:53:58 GMT 2023 , Edited by admin on Sat Dec 16 09:53:58 GMT 2023
|
PRIMARY | |||
|
6559-91-7
Created by
admin on Sat Dec 16 09:53:58 GMT 2023 , Edited by admin on Sat Dec 16 09:53:58 GMT 2023
|
PRIMARY | |||
|
74422
Created by
admin on Sat Dec 16 09:53:58 GMT 2023 , Edited by admin on Sat Dec 16 09:53:58 GMT 2023
|
PRIMARY | |||
|
122797
Created by
admin on Sat Dec 16 09:53:58 GMT 2023 , Edited by admin on Sat Dec 16 09:53:58 GMT 2023
|
PRIMARY | |||
|
1643747
Created by
admin on Sat Dec 16 09:53:58 GMT 2023 , Edited by admin on Sat Dec 16 09:53:58 GMT 2023
|
PRIMARY |
SUBSTANCE RECORD
