19186-35-7

19186-35-7 structure

Name: Deoxypodophyllotoxin
Chemical Name: (-)-Desoxypodophyllotoxin
CAS Number: 19186-35-7
Molecular Formula: C₂₂H₂₂O₇
Molecular Weight: 398.406
Catalog: Natural product Lignans
Create Date: 2018-05-09 08:00:00
Modify Date: 2024-01-05 20:05:28
Deoxypodophyllotoxin (DPT), a derivative of podophyllotoxin, is a lignan with potent antimitotic, anti-inflammatory and antiviral properties isolated from rhizomes of Sinopodophullumhexandrum (Berberidaceae). Deoxypodophyllotoxin, targets the microtubule, has a major impact in oncology not only as anti-mitotics but also as potent inhibitors of angiogenesis[1]. Deoxypodophyllotoxin induces cell autophagy and apoptosis[2]. Deoxypodophyllotoxin evokes increase of intracellular Ca2+ concentrations in DRG neurons[3].

Name	(-)-Desoxypodophyllotoxin
Synonyms	(5R,5aR,8aR)-5-(3,4,5-Trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one Anthricin deoxypodophyllotoxin Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR)- Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR)-

Description	Deoxypodophyllotoxin (DPT), a derivative of podophyllotoxin, is a lignan with potent antimitotic, anti-inflammatory and antiviral properties isolated from rhizomes of Sinopodophullumhexandrum (Berberidaceae). Deoxypodophyllotoxin, targets the microtubule, has a major impact in oncology not only as anti-mitotics but also as potent inhibitors of angiogenesis[1]. Deoxypodophyllotoxin induces cell autophagy and apoptosis[2]. Deoxypodophyllotoxin evokes increase of intracellular Ca2+ concentrations in DRG neurons[3].
Related Catalog	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cardiovascular Disease Research Areas >> Infection Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin
In Vitro	Deoxypodophyllotoxin (25-75 nM; 6-48 hours) increases the percentage of early apoptotic cell population from 2.05 to 5.62 and 18.49% for 24 h and 48 h, respectively[1]. Deoxypodophyllotoxin (25-75 nM; 6-48 hours) treats SGC-7901 cells arrested in G2/M phase in time- and dose- dependent manners[1]. Deoxypodophyllotoxin (25-75 nM; 6-48 hours) results in a remarkably time- and dose-dependent decrease in Cdc2 and Cdc25C expression levels and increases cyclin B1 within 6h, decreases PARP, Bcl-2 and caspase-3 activity[1]. Apoptosis Analysis[1] Cell Line: SGC-7901 cells Concentration: 25, 50, 75 nM Incubation Time: 6, 12, 24, 48 hours Result: Induced apoptosis in SGC-7901 Cells. Cell Cycle Analysis[1] Cell Line: SGC-7901 cells Concentration: 25, 50, 75 nM Incubation Time: 6, 12, 24, 48 hours Result: Induced G2/M cell cycle arrest in SGC-7901 Cells Western Blot Analysis[1] Cell Line: SGC-7901 cells Concentration: 25, 50, 75 nM Incubation Time: 6, 12, 24, 48 hours Result: Altered the expression of cyclin B1, Cdc2,Cdc25C, p-PARP, Bcl-2 and p-caspase-3 proteins.
In Vivo	Deoxypodophyllotoxin (intravenously injected; 5, 10, and 20 mg/kg; 3 times a week; 28 days) suppresses the tumors in a dose-dependent manner, the growth of tumors is inhibited by 22.19%, 47.91% and 50.93% with DPT at 5, 10 and 20 mg/kg, respectively[1]. Animal Model: Xenograft model of gastric cancer in nude mice with SGC-7901 cells[1] Dosage: 5, 10, and 20 mg/kg Administration: Intravenously injected; 5, 10, and 20 mg/kg; 3 times a week; 28 days Result: Inhibited the growth of gastric cancer tumors.
References	[1]. Wang YR, et al. Deoxypodophyllotoxin induces G2/M cell cycle arrest and apoptosis in SGC-7901 cells and inhibits tumor growth in vivo. Molecules. 2015 Jan 20;20(1):1661-75. [2]. Kim SH, et al. Deoxypodophyllotoxin induces cytoprotective autophagy against apoptosis via inhibition of PI3K/AKT/mTOR pathway in osteosarcoma U2OS cells. Pharmacol Rep. 2017 Oct;69(5):878-884. [3]. Xu P, et al. Pharmacological effect of deoxypodophyllotoxin: a medicinal agent of plant origin, on mammalian neurons. Neurotoxicology. 2010 Dec;31(6):680-6.

Density	1.3±0.1 g/cm3
Boiling Point	564.5±50.0 °C at 760 mmHg
Molecular Formula	C₂₂H₂₂O₇
Molecular Weight	398.406
Flash Point	247.0±30.2 °C
Exact Mass	398.136566
PSA	72.45000
LogP	2.44
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.587

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TP9002800

CHEMICAL NAME :: Podophyllotoxin, deoxy-

CAS REGISTRY NUMBER :: 19186-35-7

LAST UPDATED :: 198702

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C22-H22-O7

MOLECULAR WEIGHT :: 398.44

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Human HeLa cell

DOSE/DURATION :: 500 nmol/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

Hazard Codes	Xi

19186-35-7	17301-90-5
3590-93-0	155325-17-0
1021114-73-7	1158522-08-7
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6906-52-1	930439-75-1
1018584-77-4	1375289-11-4