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(S)-(+)-Camptothecin structure, CAS 7689-03-4

(S)-(+)-Camptothecin

CAS Number7689-03-4

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

Molecular FormulaC20H16N2O4

Molecular Weight348.35

Purity≥90 (HPLC)%

Density1.5±0.1 g/cm3

Boiling Point757.0±60.0 °C at 760 mmHg

Melting Point260 °C (dec.) (lit.)

Flash Point

Appearancepowder

EINECS

MSDSChineseEnglish

SymbolTransport

Signal WordWarning

Cat. No.: 2A-9008948 Purity: ≥90 (HPLC)%
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Quality Control of [ 7689-03-4 ] Purity: ≥90 (HPLC)% SDS Specification MoL

COA NMR CNMR HPLC LC-MS
Chemical & Physical Properties
CAS Number7689-03-4
Catalog No.2A-9008948
Chinese Name喜树碱
SynonymsEINECS 444-280-6; Camptothecin; d-Camptothecin; (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; (S)-(+)-Camptothecin; (4S)-4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; Camptohecin; MFCD00081076; Baicalin std.; CAMPTOTHECINE; (S)-4-ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizinol[1,2-b]quinoline-3,14(4H,12H)-dione; (+)-Camptothecin; (+)-Camptothecine
Molecular FormulaC20H16N2O4
Molecular Weight348.35
Purity≥90 (HPLC)
Density1.5±0.1 g/cm3
Boiling Point757.0±60.0 °C at 760 mmHg
Melting Point260 °C (dec.) (lit.)
Appearancepowder
Water Solubilityinsoluble
Storage Condition2-8℃
ApplicationCampathecin is a potent inhibitor of DNA topoisomerase I with an IC50 value of 679 nM.
PubChem ID24278352
MDL NumberMFCD00081076
SMILESCC[C@@]1(O)C(=O)OCC2=C1C=C3N(Cc4cc5ccccc5nc34)C2=O
InChI1S/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
InChI KeyVSJKWCGYPAHWDS-FQEVSTJZSA-N
Beilstein/REAXYS631069
NACRES CodeNA.77
UNSPSC12352200
Hazard SymbolsTransport
MSDSmsds/8948_1_7689_03_4.pdf
BioactivityCampathecin is a potent DNA enzyme topoisomerase I inhibitor, with an IC50 of 679 nM. Related Catalog Signaling Pathways >> Antibody-drug Conjugate >> ADC Cytotoxin Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase Research 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
Use ofCampathecin is a potent DNA enzyme topoisomerase I inhibitor, with an IC50 of 679 nM. Properties Articles386 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 Signaling Pathways >> Antibody-drug Conjugate >> ADC Cytotoxin Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase Research Areas >> Cancer 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]. 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 Molecular Formula C20H16N2O4 Exact Mass 348.110992 PSA 81.42000 Index of Refraction 1.746 InChIKey VSJKWCGYPAHWDS-FQEVSTJZSA-N Water Solubility insoluble
Transport InfoShipping Name: UN
MSDS Transport InfoModule 14. Shipping information 14.1 UN dangerous goods number European Land Transport Danger Regulations: 1544 International Maritime Transport Danger Regulations: 1544 International Air Transport Danger Regulations: 1544 14.2 United Nations shipping name European Land Transport Dangerous Regulations: ALKALOIDS, SOLID, N.O.S. ((S)-(+)-Camptothecin) IMDG Code: ALKALOIDS, SOLID, N.O.S. ((S)-(+)-Camptothecin) IMDG: Alkaloids, solid, n.o.s. ((S)-(+)-Camptothecin) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Land Transport Danger Regulations: III International Maritime Transport Danger Regulations: III International Air Transport Danger Regulations: III
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