Camptothecin (Campathecin)

Alias: Camptothecin; NSC-100880; (S)-(+)-Camptothecin; (S)-(+)-Camptothecin; NSC100880; Camptothecine; NSC 100880; d-Camptothecin; 20(S)-Camptothecine; (+)-Camptothecin; CPT
Cat No.:V1391 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.
Camptothecin (Campathecin) Chemical Structure CAS No.: 7689-03-4
Product category: Topoisomerase
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

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.

Biological Activity I Assay Protocols (From Reference)
Targets
Topoisomerase I ( IC50 = 679 nM ); Camptothecins
ln Vitro

Camptothecin, a plant alkaloid, was first isolated from Camptotheca acuminate in 1966.[1] It has been observed that camptothecin stops cells in their tracks during the S phase of mitosis. With IC50 values ranging from 37 nM to 48 nM, camptothecin demonstrates nanomolar potency in cytotoxicity against numerous human tumor cell lines, including HT29, LOX, SKOV3, and SKVLB.[2] At an IC50 of 13 μM, camptothecin causes apoptosis in primary mouse hepatocytes when combined with TNF. Moreover, camptothecin inhibited the expression of TNF-receptor associated factor 2 (TRAF2), X-linked inhibitor of apoptosis protein (X-IAP), and FLICE-inhibitory protein (FLIP), as well as the TNF-induced NF-κB Activation.[4] In HCT116 cells, camptothecin (5 μM) causes the mixed lineage leukemia 5 (MLL5) protein to be broken down by proteasomes, which phosphorylates p53 at Ser392. [5] Owing to camptothecin's poor solubility and unfavorable effects, a number of camptothecin analogues have been created; two of these, topotecan and irinotecan, have FDA approval and are used in cancer chemotherapy.

ln Vivo
Camptothecin (8 mg/kg) exhibits total growth inhibition and regression in mice given xenografts of different tumors, such as tumors of the ovaries, stomach, colon, lung, and breast.[3] Liver damage is induced in mice by combinations of 50 mg/kg Camptothecin and TNF (5 and 7 μg/kg), but not by Camptothecin alone.[4]
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.
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.
Animal Protocol
Nude mice (NIH-I high fertility strain) bearing xenografts of CASE, SW48, DOY, SPA, and CLO cells; 0–8 mg/kg; Administered via i.m. or i.v. injection
Nude mice (NIH-I high fertility strain) bearing xenografts of CASE, SW48, DOY, SPA, and CLO cells
References

[1]. J Am Chem Soc, 1966, 88 (16), 3888–3890.

[2]. J Med Chem . 1995 Feb 3;38(3):395-401.

[3]. Cancer Res . 1991 Jun 1;51(11):3052-5.

[4]. Hepatology . 2004 May;39(5):1311-20.

[5]. Oncogene, 2011, 30(33), 3599-3611.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H16N2O4
Molecular Weight
348.35
Exact Mass
348.11
Elemental Analysis
C, 68.96; H, 4.63; N, 8.04; O, 18.37
CAS #
7689-03-4
Appearance
Light yellow solid powder
SMILES
CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
InChi Key
VSJKWCGYPAHWDS-FQEVSTJZSA-N
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
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
Synonyms
Camptothecin; NSC-100880; (S)-(+)-Camptothecin; (S)-(+)-Camptothecin; NSC100880; Camptothecine; NSC 100880; d-Camptothecin; 20(S)-Camptothecine; (+)-Camptothecin; CPT
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 3~6.3 mg/mL (8.6~17.9 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Solubility (In Vivo)
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.

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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.

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Clinical Trial Information
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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