Teniposide

Modify Date: 2024-01-02 16:05:48

Teniposide Structure
Teniposide structure
Common Name Teniposide
CAS Number 29767-20-2 Molecular Weight 656.654
Density 1.6±0.1 g/cm3 Boiling Point 864.3±65.0 °C at 760 mmHg
Molecular Formula C32H32O13S Melting Point 274 - 277ºC
MSDS Chinese USA Flash Point 476.5±34.3 °C
Symbol GHS08
GHS08
Signal Word Danger

 Use of Teniposide


Teniposide is a podophyllotoxin derivative, acts as a topoisomerase II inhibitor, and used as a chemotherapeutic agent.

 Names

Name teniposide
Synonym More Synonyms

 Teniposide Biological Activity

Description Teniposide is a podophyllotoxin derivative, acts as a topoisomerase II inhibitor, and used as a chemotherapeutic agent.
Related Catalog
Target

Topoisomerase II

In Vitro Teniposide is a topoisomerase II inhibitor. Teniposide (VM-26, 0.15-45 mg/L) inhibits the proliferation of Tca8113 cells in a dose-dependent manner, with an IC50 of 0.35 mg/L. Teniposide (5 mg/L) induces apoptosis of Tca8113 cells. Teniposide (5.0 mg/L) causes cell arrested at G2/M phase in Tca8113 cells[2]. Teniposide is active on primary cultured glioma cells from patients, when the level of miR-181b is high in the cells, with an IC50 of 1.3 ± 0.34 μg/mL. Cells treated with teniposide with low MDM2 have decreased viability compared with control cells, and the IC50 decreases from 5.86 ± 0.36 μg/mL to 2.90 ± 0.35 μg/mL upon MDM2 suppression. Teniposide also inhibits the viability of glioma cell with high level of miR-181b, through mediation of MDM2[3].
In Vivo Teniposide (0.5 mg/kg, i.p.) significantly increases micronucleated polychromatic erythrocyte (MNPCE) frequencies, which is directly related to bone marrow toxicity as significant suppression of bone marrow is noted. Teniposide (24 mg/kg, i.p.) markedly decreases the frequencies of BrdU-labelled sperm. Teniposide (12, 24 mg/kg, i.p.) also dramatically induces disomic sperm in the germ cell of male mice[1].
Cell Assay Logarithmically growing Tca8113 cells are trypsinized and made into single cell suspension then plated in 96-well culture plate at a concentration of 5 × 104 cells/well, eight columns for Teniposide and seven columns for CDDP in each plate, 3 wells in each column. After 24 hours of incubation, the medium of the 3 wells in each column are replaced with medium containing Teniposide of 0.15 mg/L, 0.5 mg/L, 1.5 mg/L, 5.0 mg/L, 15 mg/L and 45 mg/L or CDDP of 0.1 mg/L, 0.3 mg/L, 1.0 mg/L, 3.0 mg/L and 9.0 mg/L, respectively. Blank control wells are added medium without drugs. Cells are then cultured for another 24 hours, 48 hours, 72 hours, 96 hours and 120 hours. The supernatants are removed and 20 μL MTT solution is added in each well, followed with another 4 hours of culture. The supernatants are discarded carefully and 200 μL dimethyl sulphoxide (DMSO) is added and shaken vigorously to dissolve the purple precipitation formation. Optical density (OD) of each well is tested using Spectrophotometer with a wavelength of 450 nm. The experiment is repeated in triplicate[2].
Animal Admin Animals (mice) are treated with 0.5 mg/kg teniposide and bone marrow is sampled 24 h after treatment. Colchicine and mitomycin C are used as a positive control aneugen and clastogen, respectively, at the dose of 2 mg/kg each. Bone marrow smears are prepared and stained with May-Gruenwald/Giemsa solutions. At least four slides are made for each animal and allowed to dry overnight. One slide per animal is stained with May-Gruenwald/Giemsa solutions for conventional assessment of the micronuclei (MN) frequencies in polychromatic erythrocytes (PCEs) and normochromatic erythrocytes (NCEs). The remaining unstained slides are stored at −20°C for the distinction between the clastogenic and aneugenic effects by identifying the origin of MN with the mouse DNA probes. Per animal, 1000 PCE of coded slides are scored for the presence of MN. In addition, the number of PCEs among 1000 NCE per animal is recorded to evaluate bone marrow suppression and mitotic activity is calculated as %PCE = [PCE/(PCE + NCE)] × 100[1].
References

[1]. Attia SM, et al. Molecular cytogenetic evaluation of the aneugenic effects of teniposide in somatic and germinal cells of male mice. Mutagenesis. 2012 Jan;27(1):31-9.

[2]. Li J, et al. Topoisomerase II trapping agent teniposide induces apoptosis and G2/M or S phase arrest of oral squamous cell carcinoma. World J Surg Oncol. 2006 Jul 6;4:41.

[3]. Sun YC, et al. MiR-181b sensitizes glioma cells to teniposide by targeting MDM2. BMC Cancer. 2014 Aug 25;14:611.

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Boiling Point 864.3±65.0 °C at 760 mmHg
Melting Point 274 - 277ºC
Molecular Formula C32H32O13S
Molecular Weight 656.654
Flash Point 476.5±34.3 °C
Exact Mass 656.156372
PSA 189.07000
LogP 1.71
Vapour Pressure 0.0±0.3 mmHg at 25°C
Index of Refraction 1.697
Storage condition -20°C Freezer

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KC0180000
CHEMICAL NAME :
Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-2-thenylidene-beta-D-glucopyranoside)
CAS REGISTRY NUMBER :
29767-20-2
LAST UPDATED :
199801
DATA ITEMS CITED :
44
MOLECULAR FORMULA :
C32-H32-O13-S
MOLECULAR WEIGHT :
656.70

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
9579 mg/kg
TOXIC EFFECTS :
Behavioral - anorexia (human) Gastrointestinal - nausea or vomiting Skin and Appendages - hair
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human
DOSE/DURATION :
26 mg/kg/10D-I
TOXIC EFFECTS :
Blood - agranulocytosis Blood - aplastic anemia Blood - changes in bone marrow (not otherwise specified)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human
DOSE/DURATION :
132 mg/kg/7W-I
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting Blood - leukopenia
TYPE OF TEST :
LD17 - Lethal Dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
15 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea Blood - leukopenia
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
29570 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
31560 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
168 mg/kg/4W-I
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
18 mg/kg/7D-I
TOXIC EFFECTS :
Gastrointestinal - other changes Liver - changes in liver weight Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Specific Developmental Abnormalities - respiratory system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1 mg/kg
SEX/DURATION :
female 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - oogenesis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material)
TYPE OF TEST :
Micronucleus test

MUTATION DATA

TYPE OF TEST :
DNA damage
TEST SYSTEM :
Primate - monkey Kidney
DOSE/DURATION :
100 umol/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 48,1722,1988 *** REVIEWS *** TOXICOLOGY REVIEW EJCAAH European Journal of Cancer. (Oxford, UK) V.1-17(6), 1965-1981. For publisher information, see EJCODS. Volume(issue)/page/year: 9,477,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X7293 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 14 (estimated) No. of Female Employees: 14 (estimated)

 Safety Information

Symbol GHS08
GHS08
Signal Word Danger
Hazard Statements H350
Precautionary Statements P201-P308 + P313
Hazard Codes Xi
Risk Phrases R36/37/38
Safety Phrases S36
RIDADR 3276
WGK Germany 3
RTECS KC0180000

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 Synonyms

etp
Pipodophyllotoxin VM 26
Teniposide/VM-26
vm-26
(5S,5aR,8aR,9R)-9-(4-Hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-(2-thienylmethylene)-β-D-glucopyranoside
vehem
Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4,6-O-((R)-2-thienylmethylene)-β-D-glucopyranosyl)oxy)-, (5R,5aR,8aR,9S)-
Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-[(R)-2-thienylmethylene]-β-D-glucopyranosyl]oxy]-, (5R,5aR,8aR,9S)-
Teniposide
Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-(2-thienylmethylene)-β-D-glucopyranosyl]oxy]-, (5R,5aR,8aR,9S)-
Teniposide(VuMon)
EINECS 249-831-2
MFCD00866516
Vumon