Campathecin

Modify Date: 2024-01-01 18:17:00

Campathecin Structure
Campathecin structure
 Common Name Campathecin
CAS Number 7689-03-4 Molecular Weight 348.352
Density 1.5±0.1 g/cm3 Boiling Point 757.0±60.0 °C at 760 mmHg
Molecular Formula C20H16N2O4 Melting Point 260 °C (dec.)(lit.)
MSDS Chinese USA Flash Point 411.6±32.9 °C
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Campathecin


Campathecin is a potent DNA enzyme topoisomerase I inhibitor, with an IC50 of 679 nM.

 Names

Name camptothecin
Synonym More Synonyms

 Campathecin Biological Activity

Description Campathecin is a potent DNA enzyme topoisomerase I inhibitor, with an IC50 of 679 nM.
Related Catalog
Target

Topoisomerase I:679 nM (IC50)

In Vitro [3H]BrCPT labeling of topoisomerase I is enhanced greatly by the presence of DNA; very little labeling of isolated topoisomerase I or isolated DNA occurrs. Even in the presence of DNA, [3H]BrCPT labeling of topoisomerase I is inhibited by camptothecin, suggesting that both CPT and BrCPT bind to the same site on the DNA-topoisomerase I binary complex[1]. With increasing concentrations of camptothecin, closed circular pRR322 DNA (form I) is converted to nicked circular DNA (form 11). This apparent nicking activitv of camptothecin required DNA topoisomerase I[2].
Kinase Assay Each reaction mixture (200 μL, total volume) contained 2 μg of supercoiled pDPT2789 DNA (2.4 nM plasmid concentration), 50 mM Tris-HCl, pH 7.5, 120 mM KCl, 10 mM MgCl2, 0.5 mM EDTA, 0.05% dimethyl sulfoxide, 1% methanol, 100 μg/mL BSA, 4.3 ng of calf thymus topoisomerase I (0.26 nM), and a CPT derivative. The reaction mixture is incubated at 37°C, and at the indicated times 20-μL aliquots are removed and terminated by the addition of 5 μL of SDS/Ficoll stop mix (final concentrations, 0.5% SDS, 2% Ficoll, 0.025% bromphenol blue). The samples are loaded onto a 1% agarose gel and analyzed by electrophoresis.
References

[1]. Hertzberg RP, et al. Irreversible trapping of the DNA-topoisomerase I covalent complex. Affinity labeling of the camptothecin binding site. J Biol Chem. 1990 Nov 5;265(31):19287-95.

[2]. Hsiang YH, et al. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. J Biol Chem. 1985 Nov 25;260(27):14873-8.

[3]. Luzzio MJ, et al. Synthesis and antitumor activity of novel water soluble derivatives of camptothecin as specific inhibitors of topoisomerase I. Synthesis and antitumor activity of novel water soluble derivatives of camptothecin as specific inhibitors of topoisomerase I.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 757.0±60.0 °C at 760 mmHg
Melting Point 260 °C (dec.)(lit.)
Molecular Formula C20H16N2O4
Molecular Weight 348.352
Flash Point 411.6±32.9 °C
Exact Mass 348.110992
PSA 81.42000
LogP 1.60
Vapour Pressure 0.0±2.7 mmHg at 25°C
Index of Refraction 1.746
Water Solubility insoluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UQ0492000
CAS REGISTRY NUMBER :
7689-03-4
LAST UPDATED :
199706
DATA ITEMS CITED :
29
MOLECULAR FORMULA :
C20-H16-N2-O4
MOLECULAR WEIGHT :
348.38
WISWESSER LINE NOTATION :
T F6 D6 C566 BN HVO LVN NHT&&&&J GQ G2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
50100 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 :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
64 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
38 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :
DNA damage
TEST SYSTEM :
Primate - monkey Kidney
DOSE/DURATION :
25 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

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements Missing Phrase - N15.00950417
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T:Toxic;
Risk Phrases R25
Safety Phrases S45-S36/37/39-S26
RIDADR UN 1544 6.1/PG 3
WGK Germany 3
RTECS UQ0492000

 Synthetic Route

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 Synonyms

EINECS 444-280-6
Camptothecin
d-Camptothecin
1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-
(S)-4-ethyl-4-hydroxy-1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
(S)-4-ethyl-4-hydroxy-1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione
CaMpathecin
1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (4S)-
(S)-(+)-Camptothecin
(4S)-4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (S)-
Camptohecin
MFCD00081076
Baicalin std.
CAMPTOTHECINE
1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-, (4S)-
(S)-4-ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizinol[1,2-b]quinoline-3,14(4H,12H)-dione
(+)-Camptothecin
(+)-Camptothecine
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