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4'-Demethylepipodophyllotoxin

Names

[ CAS No. ]:
6559-91-7

[ Name ]:
4'-Demethylepipodophyllotoxin

[Synonym ]:
(5R,5aR,8aR,9S)-9-Hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
4'-DMEP
4'-Demethylepipodophyllotoxin
4-DEMETHYL EIPODOPHYLLOTOXIN
4-Domethylpodophyllotoxin,4'-demethyl-epi-Podophyllotoxin
Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-
4'-demethyl-9-epipodophyllotoxin
4'-demethyl-epipodophyllotoxin
4'-demethyl-4-epipodophyllotoxin
4'-O-demethyl-4-epipodophyllotoxin
4'-DEMETHYLEPIPODOPHYLLOTOXINE
DMEP
MFCD00189421
4'-O-demethylepipodophyllotoxin
etoposide aglycone
4-Demethylepipodo phyllotoxin

Biological Activity

[Description]:

4'-Demethylepipodophyllotoxin(4'-DMEP) is a key intermediate compound for the preparation of podophyllotoxin-type anti-cancer drugs; a potent inhibitor of microtubule assembly.IC50 Value: 0.31uM(EC5 0in HL60 cell, MTT assay, 48h); 0.37uM(EC50 in HepG2 cell, MTT assay, 48h) [1]Target: microtubulein vitro: 4-TMP-DMEP showed strong cytotoxicity activity against the above-mentioned five tumor cell lines. The EC50s of 4-TMP-DMEP against these tumor cell lines ranged from 0.24 to 0.11 μM, which were 0.29 to 3618 times lower than that of DMEP [1].in vivo: Treatment of animals with DMEP (until the end of the experiment), 30 min before TPA treatment, significantly reduced the tumor incidence, tumor volume and the conversion efficiency of papillomas to squamous cell carcinomas. The tumor formation and growth was also delayed by DMEP pre-treatment [2].

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin
Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin
Research Areas >> Cancer

[References]

[1]. Tang YJ, Zhao W, Li HM. Novel tandem biotransformation process for the biosynthesis of a novel compound, 4-(2,3,5,6-tetramethylpyrazine-1)-4'-demethylepipodophyllotoxin. Appl Environ Microbiol. 2011 May;77(9):3023-34.

[2]. Dhawan D, Balasubramanian S, Amonkar AJ, Chemopreventive effect of 4'-demethyl epipodophyllotoxin on DMBA/TPA-induced mouse skin carcinogenesis. Carcinogenesis. 1999 Jun;20(6):997-1003.


[Related Small Molecules]

Nocodazole | Monomethyl auristatin E | VcMMAE | Mertansine | Eribulin mesylate | Epothilone D | Vinorelbine (ditartrate) | epothilone B | McMMAF | MMAF (Hydrochloride) | Ixabepilone | Taltobulin | Estramustine phosphate sodium | Ansamitocin P-3 | Combretastatin A4 disodium phosphate

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
626.5±55.0 °C at 760 mmHg

[ Melting Point ]:
246-248ºC

[ Molecular Formula ]:
C21H20O8

[ Molecular Weight ]:
400.379

[ Flash Point ]:
224.4±25.0 °C

[ Exact Mass ]:
400.115814

[ PSA ]:
103.68000

[ LogP ]:
0.71

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.638

[ Storage condition ]:
-20°C Freezer

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LV2476200
CAS REGISTRY NUMBER :
6559-91-7
BEILSTEIN REFERENCE NO. :
1358259
LAST UPDATED :
199612
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C21-H20-O8
MOLECULAR WEIGHT :
400.41
WISWESSER LINE NOTATION :
T E5 C665 FVO NO PO OHTT&&J DR DQ CO1 EO1& JQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Human HeLa cell
DOSE/DURATION :
10 umol/L
REFERENCE :
BICHAW Biochemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1962- Volume(issue)/page/year: 15,5443,1976

Synthetic Route

Precursor & DownStream


Related Compounds