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| 50mg |
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| 250mg |
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| 500mg |
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| 1g |
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Purity: ≥98%
Camptothecin (also known as Campathecin; CPT; NSC-100880), a naturally occurring quinoline alkaloid, is a potent and specific inhibitor of DNA enzyme topoisomerase I (Topo I) with potent antitumor activity. In a cell-free assay, it inhibits topoisomerase I (Topo I) with an IC50 of 0.68 μM. The bark and stem of Camptotheca acuminata can be used to isolate camptothecin, which is licensed for use in Traditional Chinese Medicine as an anticancer medication. In initial clinical trials, it demonstrated impressive anticancer activity; however, it also had low solubility and adverse drug reaction. Due to these drawbacks, medicinal and synthetic chemists have successfully created a number of syntheses of camptothecin and its derivatives in an effort to increase the chemical's advantages.
| Targets |
Topoisomerase I ( IC50 = 679 nM ); Camptothecins
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| ln Vitro |
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| ln Vivo |
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| Enzyme Assay |
The calf thymus is the source of topoisomerase I, which is absent from topoisomerase II. Every reaction is conducted in microtiter plates using 10 mL volumes of reaction buffer (50 mM Tris-HCl, pH 7.5, 100 mM KCl, 0.5 mM EDTA, and 30 pg/mL BSA). In 96-well microtiter plates, topoisomerase enzyme and 32P end-labeled pBR322 DNA are added after 10 mg/mL of camptothecin has been dissolved in DMSO and serially diluted. After the reaction mixture is incubated for 30 minutes at room temperature, 2 mL of a solution containing proteinase K and sodium dodecyl sulfate (1.6% and 0.14 mg/mL final concentrations, respectively) is added to stop the reaction. The samples are electrophoresed in 1.5% agarose gels in TBE buffer after the plates are heated to 50 °C for 30 minutes and 10 mL of standard stop mixture containing 0.45 N NaOH is added. Gels are exposed to X-ray film after being blotted on nitrocellulose paper, dried, and polished. The log drug concentration is plotted against the units of cleavage, which are computed from the autoradiographs. We then obtain the IC50 values.
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| Cell Assay |
In 96-well microtiter plates, tumor cells are plated at a density of 1500–4000 cells per well in 100 μL of medium, and they are left to adhere for the entire night. After 48 hours of camptothecin incubation, cells are incubated for an additional 48 hours in fresh medium. Quadruplicates of each concentration of camptothecin are added. After treating the cells with MTT for four hours, the reduced dye product is removed from the cells using 0.2 mL of DMSO and then 50 μL of Sorensen's buffer. After giving the plates a quick shake, the absorbance at 570 nm is measured and recorded. An MTT assay data set is fitted with curves using a four-parameter logistic equation.
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| Animal Protocol |
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| Additional Infomation |
Camptothecin is a pyranoindolizinoquinoline that is pyrano[3',4':6,7]indolizino[1,2-b]quinoline which is substituted by oxo groups at positions 3 and 14, and by an ethyl group and a hydroxy group at position 4 (the S enantiomer). It has a role as an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an antineoplastic agent, a genotoxin and a plant metabolite. It is a pyranoindolizinoquinoline, a tertiary alcohol, a delta-lactone and a quinoline alkaloid.
Camptothecin is an alkaloid isolated from the stem wood of the Chinese tree, Camptotheca acuminata. This compound selectively inhibits the nuclear enzyme DNA topoisomerase, type I. Several semisynthetic analogs of camptothecin have demonstrated antitumor activity. Camptothecin has been reported in Ophiorrhiza liukiuensis, Nothapodytes nimmoniana, and other organisms with data available. Camptothecin is an alkaloid isolated from the Chinese tree Camptotheca acuminata, with antineoplastic activity. During the S phase of the cell cycle, camptothecin selectively stabilizes topoisomerase I-DNA covalent complexes, thereby inhibiting religation of topoisomerase I-mediated single-strand DNA breaks and producing potentially lethal double-strand DNA breaks when encountered by the DNA replication machinery. (NCI) An alkaloid isolated from the stem wood of the Chinese tree, Camptotheca acuminata. This compound selectively inhibits the nuclear enzyme DNA TOPOISOMERASES, TYPE I. Several semisynthetic analogs of camptothecin have demonstrated antitumor activity. Drug Indication Investigated for the treatment of cancer. Mechanism of Action Camptothecin binds to the topoisomerase I and DNA complex resulting in a ternary complex, stabilizing it and preventing DNA re-ligation and therefore causes DNA damage which results in apoptosis. |
| Molecular Formula |
C20H16N2O4
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| Molecular Weight |
348.35
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| Exact Mass |
348.11
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| Elemental Analysis |
C, 68.96; H, 4.63; N, 8.04; O, 18.37
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| CAS # |
7689-03-4
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| Related CAS # |
7689-03-4; 25387-67-1 (sodium)
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| PubChem CID |
24360
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| Appearance |
Light yellow solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
757.0±60.0 °C at 760 mmHg
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| Melting Point |
260 °C (dec.)(lit.)
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| Flash Point |
411.6±32.9 °C
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| Vapour Pressure |
0.0±2.7 mmHg at 25°C
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| Index of Refraction |
1.746
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| LogP |
1.6
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
26
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| Complexity |
742
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O1C([C@](C([H])([H])C([H])([H])[H])(C2C([H])=C3C4C(=C([H])C5=C([H])C([H])=C([H])C([H])=C5N=4)C([H])([H])N3C(C=2C1([H])[H])=O)O[H])=O
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| InChi Key |
VSJKWCGYPAHWDS-FQEVSTJZSA-N
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| InChi Code |
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
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| Chemical 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
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 10 mg/mL (28.71 mM) in 15% Cremophor EL + 85% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 30% PEG400+0.5% Tween80+5% Propylene glycol : 30 mg/mL (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8707 mL | 14.3534 mL | 28.7068 mL | |
| 5 mM | 0.5741 mL | 2.8707 mL | 5.7414 mL | |
| 10 mM | 0.2871 mL | 1.4353 mL | 2.8707 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT02769962 | Recruiting | Drug: EP0057 Drug: olaparib |
Urothelial Carcinoma Urothelial Cancer |
National Cancer Institute (NCI) |
May 9, 2016 | Phase 1 Phase 2 |
| NCT00277082 | Completed | Drug: 9-NC in aerosol reservoir |
Corpus Uteri Lung Cancer |
University of New Mexico | August 2003 | N/A |
| NCT00249990 | Completed | Drug: 9-NC in aerosol reservoir |
Corpus Uteri Endometrial Cancer |
University of New Mexico | April 2003 | Phase 2 |
| NCT00250068 | Completed | Drug: Liposomal 9- Nitrocamptothecin |
Lung Diseases Cancer |
University of New Mexico | April 2003 | Phase 2 |
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