4'-Demethylepipodophyllotoxin

Modify Date: 2024-01-02 17:04:51

4'-Demethylepipodophyllotoxin structure	Common Name	4'-Demethylepipodophyllotoxin
	CAS Number	6559-91-7	Molecular Weight	400.379
	Density	1.4±0.1 g/cm3	Boiling Point	626.5±55.0 °C at 760 mmHg
	Molecular Formula	C₂₁H₂₀O₈	Melting Point	246-248ºC
	MSDS	N/A	Flash Point	224.4±25.0 °C

Use of 4'-Demethylepipodophyllotoxin

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].

Name	4'-demethylepipodophyllotoxin
Synonym	More Synonyms

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.

Description

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.

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

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

Precursor 4
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DownStream 10
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