Teniposide - Moligand™, ≥98% , DNA topoisomerase II inhibitor, CAS No.29767-20-2, DNA topoisomerase II inhibitor

CAS: 29767-20-2 Cat. No.: T125922 Molecular Weight: 656.65 EC Number: 249-831-2 PubChem CID: 452548

GRADE & PURITY Moligand™, ≥98%

Synonyms

4'-Demethylepipodophyllotoxin 9-(4,6-O-2-thenylidene-beta-D-glucopyranoside) | Vehem | VM26 | VM-26 | (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(2-thienyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethox

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

A derivative of podophyllotoxin that has shown cytostatic effect & inhibition of topoisomerase II.

Specifications

Synonyms

4'-Demethylepipodophyllotoxin 9-(4, 6-O-2-thenylidene-beta-D-glucopyranoside) | Vehem | VM26 | VM-26 | (5S, 5aR, 8aR, 9R)-5-[[(2R, 4aR, 6R, 7R, 8R, 8aS)-7, 8-dihydroxy-2-(2-thienyl)-4, 4a, 6, 7, 8, 8a-hexahydropyrano[3, 2-d][1, 3]dioxin-6-yl]oxy]-9-(4-hydroxy-3, 5-dimethox

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Teniposide is a glycoside-derivative of podophyllotoxin, has cytostatic effect. Teniposide inhibits Topo II(topoisomerase II)while induces apoptosis.Topoisomerase II inhibitor. A podophyllotoxin derivative. Induces apoptosis in vitro and in vivo .

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

DNA topoisomerase II inhibitor

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Product Properties

• ALogP: 1.2

Names and Identifiers

• Pubchem Sid: 488189868
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488189868
• Canonical Smiles: COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)OC6C(C(C7C(O6)COC(O7)C8=CC=CS8)O)O
• IUPAC Name: (5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• InChIKey: NRUKOCRGYNPUPR-QBPJDGROSA-N
• INCHI: 1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31+,32-/m0/s1
• Isomeric SMILES: COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)O[C@H]6[C@@H]([C@H]([C@H]7[C@H](O6)CO[C@H](O7)C8=CC=CS8)O)O
• PubChem CID: 452548
• Molecular Weight: 656.65

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lignans, neolignans and related compounds
    • Class Lignan lactones
      • Subclass Podophyllotoxins

• Kingdom: Organic compounds
• Superclass: Lignans, neolignans and related compounds
• Class: Lignan lactones
• Subclass: Podophyllotoxins
• Intermediate Tree Nodes: Not available
• Direct Parent: Podophyllotoxins
• Alternative Parents: Aryltetralin lignans Furanonaphthodioxoles Tetralins Pyranodioxins Dimethoxybenzenes Methoxyphenols Benzodioxoles Anisoles Phenoxy compounds Alkyl aryl ethers 1,3-dioxanes Oxanes Gamma butyrolactones Monosaccharides Tetrahydrofurans Heteroaromatic compounds Thiophenes Carboxylic acid esters 1,2-diols Secondary alcohols Acetals Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Carbonyl compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Podophyllotoxin - 1-aryltetralin lignan - Linear furanonaphthodioxole - Naphthofuran - Methoxyphenol - Pyranodioxin - Tetralin - M-dimethoxybenzene - Dimethoxybenzene - Benzodioxole - Phenoxy compound - Phenol ether - Anisole - Methoxybenzene - Alkyl aryl ether - Phenol - Gamma butyrolactone - Oxane - Meta-dioxane - Monosaccharide - Benzenoid - Monocyclic benzene moiety - Tetrahydrofuran - Heteroaromatic compound - Thiophene - Secondary alcohol - Lactone - 1,2-diol - Carboxylic acid ester - Acetal - Oxacycle - Organoheterocyclic compound - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Ether - Organic oxygen compound - Organooxygen compound - Carbonyl group - Alcohol - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TOP2A Tclin DNA topoisomerase 2-alpha (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

F2 Tclin Thrombin (11687 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TOP1 Tclin DNA topoisomerase I (7553 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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MAOB Tclin Monoamine oxidase B (8835 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH3 Tclin Histamine H3 receptor (10389 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Homo sapiens (32628 Activities)

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CCRF-CEM (65223 Activities)

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MCF7 (126967 Activities)

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MRC5 (9203 Activities)

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PC-3 (62116 Activities)

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A549 (127892 Activities)

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RPMI 8402 (281 Activities)

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GLC4 cell line (37 Activities)

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HMEC (560 Activities)

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HepG2 (196354 Activities)

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HeLa (62764 Activities)

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CWR22R (2180 Activities)

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ABCG2 Tchem ATP-binding cassette sub-family G member 2 (4927 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

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ABCB11 Tchem Bile salt export pump (2311 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ABCC3 Tbio Canalicular multispecific organic anion transporter 2 (718 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)

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ABCC6 Tbio Multidrug resistance-associated protein 6 (18 Activities)

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L02 (4864 Activities)

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Associated Targets(non-human)

Top2 DNA topoisomerase II (15 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

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C6 (2371 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in acetone, dimethyl formamide, methanol (slightly), and DMSO (10 mg/ml). Insoluble in water.
• Sensitivity: Heat sensitive
• Specific Rotation[α]: -111° (C=1,CHCl3:MeOH=9:1)
• Melt Point(°C): 247 °C(dec.)
• Molecular Weight: 656.700 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 6
• Exact Mass: 656.156 Da
• Monoisotopic Mass: 656.156 Da
• Topological Polar Surface Area: 189.000 Ų
• Heavy Atom Count: 46
• Formal Charge: 0
• Complexity: 1090.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yifan Wu, Xiaoxia Gong, Jianzhong Shen, Kui Zhu.  (2023)  Postantibiotic leukocyte enhancement-mediated reduction of intracellular bacteria by macrophages.  Journal of Advanced Research,      [PMID:37290606] [10.1016/j.jare.2023.05.010]

2. Chunsheng Wu, Xiangting Yi, Renzhi Xu, Maokuan Zhang, Yan Xu, Yan Ma, Li Gao, Zhengbao Zha.  (2020)  Biodistribution of etoposide via intratumoral chemotherapy with etoposide-loaded implants.  DRUG DELIVERY,      [PMID:32611260] [10.1080/10717544.2020.1787558]