CAS 29767-20-2|Teniposide

Introduction：Basic information about CAS 29767-20-2|Teniposide, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Teniposide BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Articles42
7. Synonyms

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	ChineseUSA	Flash Point	476.5±34.3 °C
Symbol	GHS08	Signal Word	Danger

Names

Name	teniposide
Synonym	More Synonyms

Teniposide BiologicalActivity

Description	Teniposide is a podophyllotoxin derivative, acts as a topoisomerase II inhibitor, and used as a chemotherapeutic agent.
Related Catalog	Signaling Pathways >>Cell Cycle/DNA Damage >>TopoisomeraseResearch Areas >>Cancer
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
InChIKey	NRUKOCRGYNPUPR-QBPJDGROSA-N
SMILES	COc1cc(C2c3cc4c(cc3C(OC3OC5COC(c6cccs6)OC5C(O)C3O)C3COC(=O)C23)OCO4)cc(OC)c1O
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
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

Articles42

Pathologic risk-based adjuvant chemotherapy for unilateral retinoblastoma following enucleation.

J. Pediatr. Hematol. Oncol. 36(6) , e335-40, (2014)

There are no standardized diagnostic or treatment guidelines for patients with advanced unilateral retinoblastoma.Patients with advanced unilateral retinoblastoma were prospectively treated after enuc...

Action of db-cAMP on the bystander effect and chemosensitivity through connexin 43 and Bcl-2-mediated pathways in medulloblastoma cells.

Oncol. Rep. 28(3) , 969-76, (2012)

Medulloblastoma (MB) is one of the most common malignant brain tumors of childhood and is associated with a poor prognosis. Gap-junctional intercellular communication (GJIC) is an important mode for c...

Dose intensification of methotrexate and cytarabine during intensified continuation chemotherapy for high-risk B-precursor acute lymphoblastic leukemia: POG 9406: a report from the Children's Oncology Group.

J. Pediatr. Hematol. Oncol. 36(5) , 353-61, (2014)

To determine the efficacy and toxicity of higher dose versus standard dose intravenous methotrexate (MTX) and pulses of high-dose cytosine arabinoside with asparaginase versus standard dose cytosine a...

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

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