CAS 7689-03-4|Campathecin

Introduction：Basic information about CAS 7689-03-4|Campathecin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Campathecin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Articles386
7. Synonyms

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	ChineseUSA	Flash Point	411.6±32.9 °C
Symbol	GHS06	Signal Word	Danger

Names

Name	camptothecin
Synonym	More Synonyms

Campathecin BiologicalActivity

Description	Campathecin is a potent DNA enzyme topoisomerase I inhibitor, with an IC50 of 679 nM.
Related Catalog	Signaling Pathways >>Antibody-drug Conjugate >>ADC CytotoxinSignaling Pathways >>Cell Cycle/DNA Damage >>TopoisomeraseResearch Areas >>Cancer
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
InChIKey	VSJKWCGYPAHWDS-FQEVSTJZSA-N
SMILES	CCC1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3ccccc3nc2-1
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
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

Articles386

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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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