MW 348.4 Da, Purity >98%. Cell-permeable DNA topoisomerase inhibitor. Potent antitumour and antibiotic agent.
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Publications
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- Proceedings of the National Academy of Sciences of the United States of America 118:2021Super-resolution mapping of cellular double-strand break resection complexes during homologous recombination.Applications:Unspecified applicationReactive species:Unspecified reactive speciesDonna R Whelan,Eli RothenbergPubMed 33707212
- PLoS genetics 16:e10092562020Super-resolution visualization of distinct stalled and broken replication fork structures.Applications:Unspecified applicationReactive species:Unspecified reactive speciesDonna R Whelan et. al.PubMed 33370257
Key facts
- CAS number
- 7689-03-4
- Purity
- > 98%
- Form
- Solid
- Molecular weight
- 348.4 Da
- Molecular formula
- C20H16N2O4
- PubChem identifier
- 24360
- Nature
- Synthetic
Target data
Alternative names
DNA topoisomerase 1, DNA topoisomerase I, NUP98 fusion gene, TOP I, TOP1_HUMAN, Topoisomerase (DNA) I, Topoisomerase 1, TopoisomeraseI, Type I DNA topoisomerase
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MW 348.4 Da, Purity >98%. Cell-permeable DNA topoisomerase inhibitor. Potent antitumour and antibiotic agent.
Key facts
- CAS number
- 7689-03-4
- Purity
- > 98%
- Form
- Solid
- Molecular weight
- 348.4 Da
- Molecular formula
- C20H16N2O4
- PubChem identifier
- 24360
- Nature
- Synthetic
- Solubility
Soluble in DMSO to 5 mM.
- Biochemical name
- Camptothecin
- Biological description
Cell-permeable DNA topoisomerase inhibitor. Potent antitumour and antibiotic agent.
- Canonical SMILES
- CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
- Isomeric SMILES
- CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
- InChI
- InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1
- InChIKey
- VSJKWCGYPAHWDS-FQEVSTJZSA-N
- IUPAC name
- (19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
Storage
- Shipped at conditions
- Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
- +4°C
- Appropriate long-term storage conditions
- +4°C
- Storage information
- Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary info
- This supplementary information is collated from multiple sources and compiled automatically.
- Activity summary
Topoisomerase I also known as DNA topoisomerase I or Topo I is an important enzyme in the unwinding of the DNA double helix during processes such as replication and transcription. This enzyme has a molecular mass of approximately 91 kDa and functions by creating transient single-strand breaks in the DNA allowing relaxation of supercoils. Topoisomerase I is widely expressed in both proliferating and non-proliferating cells with higher levels seen in tissues with rapid cell division like the gastrointestinal tract and some immune cells.
- Biological function summary
Topoisomerase I plays a significant role in the modulation of DNA topology ensuring proper chromosomal functions during cellular proliferation. It serves as a single polypeptide and does not require a companion for its activity unlike other topoisomerases that may function in complexes. The enzyme’s ability to relieve torsional stress in DNA is essential for maintaining genomic stability and facilitating the smooth progression of the replication fork.
- Pathways
Topoisomerase I is vital for DNA replication and transcription processes. It works in concert with other proteins such as helicases and ligases to ensure efficient unwinding and rewinding of DNA strands. The enzyme participates in the DNA damage response pathway where it interacts with proteins like PARP1 to coordinate repair processes. Its action is important in both the S phase of the cell cycle where DNA synthesis occurs and in the G0 phase where cells are in a quiescent state.
- Associated diseases and disorders
Topoisomerase I is heavily implicated in oncogenesis with significant associations to colorectal and ovarian cancers. Its heightened activity can lead to genomic instability a hallmark of cancer development. The enzyme also relates to chemotherapeutic resistance where mutations in topoisomerase I lead to reduced drug efficacy. Furthermore inhibitors targeting topoisomerase I such as camptothecin-based drugs exploit its role in cancer aiming to induce DNA damage selectively in rapidly dividing cells. Connections to other proteins like BRCA1 are apparent in these pathways as they both contribute to the DNA repair processes in cells.
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4 product images
Chemical Structure - Camptothecin, DNA topoisomerase inhibitor (ab120115)
2D chemical structure image of ab120115, Camptothecin, DNA topoisomerase inhibitor
Immunocytochemistry/ Immunofluorescence - Camptothecin, DNA topoisomerase inhibitor (ab120115)
Anti-gamma H2A.X (phospho S139) antibody ab2893 staining γH2AX (phospho S139) in HeLa cells treated with camptothecin (ab120115), by ICC/IF. Increased nuclear expression of γH2AX (phospho S139) correlates with increased concentration of camptothecin, as described in literature.
The cells were incubated at 37°C for 3h in media containing different concentrations of ab120115 (camptothecin) in DMSO, fixed with 4% formaldehyde for 10 minutes at room temperature and blocked with PBS containing 10% goat serum, 0.3 M glycine, 1% BSA and 0.1% tween for 2h at room temperature. Staining of the treated cells with Anti-gamma H2A.X (phospho S139) antibody ab2893 (10 μg/ml) was performed overnight at 4°C in PBS containing 1% BSA and 0.1% tween. A DyLight 488 goat anti-rabbit polyclonal antibody (Goat Anti-Rabbit IgG H&L (DyLight® 488) preadsorbed ab96899) at 1/250 dilution was used as the secondary antibody. Nuclei were counterstained with DAPI and are shown in blue.
Functional Studies - Camptothecin, DNA topoisomerase inhibitor (ab120115)
HeLa cells were incubated at 37°C for 3h with vehicle control (0 μM) and different concentrations of camptothecin (ab120115). Decreased expression of γH2A.X (phospho S139) in HeLa cells correlates with an increase camptothecin concentration, as described in literature.
Whole cell lysates were prepared with RIPA buffer (containing protease inhibitors and sodium orthovanadate), 20 μg of each were loaded on the gel and the WB was run under reducing conditions. After transfer the membrane was blocked for an hour using 5% BSA before being incubated with Anti-gamma H2A.X (phospho S139) antibody ab2893 at 1 μg/ml and Anti-Histone H2A.X antibody - Nuclear Marker ab10475 at 1 μg/ml overnight at 4°C. Antibody binding was detected using an anti-rabbit antibody conjugated to HRP (Goat Anti-Rabbit IgG H&L (HRP) ab97051) at 1/10000 dilution and visualised using ECL development solution.
Functional Studies - Camptothecin, DNA topoisomerase inhibitor (ab120115)
Functional assays: Caspase 3 (active) Red Staining Kit (Cleaved Caspase-3 Staining Kit (Red) ab65617)Caspase 3 activity in Jurkat cells (3 x10e5 cells) following 24 hour exposure to 2 uM Camptothecin (ab120115) with or without 50 μM caspase inhibitor Z-VAD(OMe)-FMK (Z-VAD(OMe)-FMK, Cell permeable, irreversible pan-caspase inhibitor ab120487). Background signal subtracted, duplicates; +/- SD.
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