CAS Number86639-52-3
Synonyms7-Ethyl-10-Hydroxycamptothecin(SN-38); (4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; SN-38; MFCD06762720; SN38; 7-Ethyl-10-hydroxycamptothecine
Molecular FormulaC22H20N2O5
Molecular Weight392.40
Purity≥98 (HPLC)%
Density1.5±0.1 g/cm3
Boiling Point810.3±65.0 °C at 760 mmHg
Melting Point217 °C
Appearancepowder
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 86639-52-3 |
| Catalog No. | 2A-9009015 |
| Chinese Name | 7-乙基-10羟基喜树碱 |
| Synonyms | 7-Ethyl-10-Hydroxycamptothecin(SN-38); (4S)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; SN-38; MFCD06762720; SN38; 7-Ethyl-10-hydroxycamptothecine |
| Molecular Formula | C22H20N2O5 |
| Molecular Weight | 392.40 |
| Purity | ≥98 (HPLC) |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 810.3±65.0 °C at 760 mmHg |
| Melting Point | 217 °C |
| Appearance | powder |
| Storage Condition | Refrigerated at -20 °C |
| Packaging | III |
| Application | SN-38 is the active metabolite of the topoisomerase I inhibitor irinotecan. The IC50 of SN-38 inhibiting DNA synthesis and RNA synthesis are 0.077 and 1.3 μM, respectively. |
| HTC | 2942000000 |
| PubChem ID | 329815105 |
| MDL Number | MFCD00871873 |
| SMILES | OC1=CC2=C(CC)C(C3)=C(N=C2C=C1)C(N3C4=O)=CC5=C4COC([C@]5(O)CC)=O |
| InChI | 1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3/t22-/m0/s1 |
| InChI Key | FJHBVJOVLFPMQE-QFIPXVFZSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352204 |
| MSDS | msds/9015_1_86639_52_3.pdf |
| Bioactivity | SN-38 is an active metabolite of the Topoisomerase I inhibitor Irinotecan. SN-38 inhibits DNA and RNA synthesis with IC50s of 0.077 and 1.3 μM, respectively. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase Research Areas >> Cancer Target Topoisomerase I In Vitro The IC50 values for LoVo, HCT116, and HT29 cell lines is 20 nM, 50 nM, 130 nM, respectively. In all three SN-38 resistant cell lines Top1 activity is maintained in the presence of high concentrations of SN-38[2]. In Vivo SN-38, the active and toxic metabolite of the anticancer prodrug Irinotecan. At 30 minutes after administration, Irinotecan plasma concentrations in Slco1a/1b(−/−) mice are 1.9-fold higher than in the wild-type mice (1.89 vs. 1.01 μM, respectively), whereas SN-38 plasma concentrations of Slco1a/1b(−/−) mice are 8-fold higher compare with wild-type mice (0.4 μg/mL vs. 0.05 μg/mL, respectively). Overall plasma exposure [AUC(5-240)] of Irinotecan is 1.7-fold higher in Oatp1a/1b knockout mice versus wild-type mice (209.8±6.7 vs. 120.9±4.4 μM/min; P<0.01), and 2.9-fold higher for SN-38 (50±2.9 vs. 12±2 μM/min; P<0.001)[3]. Kinase Assay LoVo, HCT116, and HT29 cell lines are trypsinized, resuspended and counted, and for each cell line 1 million cells are pipetted to each of three eppendorf tubes on ice. Cells are pelleted (5 min centrifugation, 300 g, 4°C) and snap-frozen in dry ice and ethanol and stored at -80°C until analysis. Nuclear extracts are prepared essentially, and Top1 activity measured in titration experiments with or without added SN-38 (at concentrations stated in the text) using the standard Rolling circle Enhanced Enzyme Activity Detection (REEAD) protocol. The activity is calculated in terms of numbers of Top1 specific signals relative to the amount of signals resulting from the addition a known concentration of control circles[2]. Cell Assay In vitro SN-38 sensitivity is determined using the MTT assay. Cells are seeded in 96-well plates, and a range of SN-38 concentrations is added the following day. Following 48 h of drug exposure, the medium is discarded and the plates are incubated with medium containing MTT (0.5 mg/mL) for 3 h. Acidified (0.02 M HCl) sodium dodecyl sulphate (20 %) is added to dissolve the formed formazan. Optical density at 570 nm (and 670 nm for background) is measured, and the cell viability is calculated in percent compared to untreated cells. Experiments are repeated three times and the mean IC50 value ± standard deviation is determined. Relative resistance for each resistant cell line is calculated by dividing the mean IC50 value of the resistant cell line by the mean IC50 value of the corresponding parental cell line[2]. Animal Admin Mice[3] Female wild-type, Slco1a/1b(−/−)(Oatp1a/1b knockout), Slco1a/1b(−/−);1B1(tg), and Slco1a/1b(−/−);1B3(tg) (liver-specific OATP1B1 and OATP1B3 humanized transgenic) mice of comparable genetic background (>99% FVB) between 8 and 14 weeks of age are used. Irinotecan (20 mg/mL in water-based solution containing NaOH, lactic acid, and sorbitol) is diluted with saline (to 2 mg/mL) for administration of 10 mg/kg; 5 μL/g bodyweight are administered intravenously to mice. SN-38 is dissolved in DMSO (1 mg/mL) and 1 μL/g body weight is administered intravenously to mice to achieve a dosage of 1 mg/kg. The experiments are terminated by isoflurane anaesthesia, heparin-blood sampling by cardiac puncture followed by cervical dislocation and tissue collection. Blood samples are centrifuged at 5,200 × g for 5 minutes at 4°C and plasma is collected and stored at −30°C until analysis. References [1]. Wallin A, et al. Anticancer effect of SN-38 on colon cancer cell lines with different metastatic potential. Oncol Rep. 2008 Jun;19(6):1493-8. [2]. Jensen NF, et al. Characterization of DNA topoisomerase I in three SN-38 resistant human colon cancer cell lines reveals a newpair of resistance-associated mutations. J Exp Clin Cancer Res. 2016 Mar 31;35:56. [3]. Stewart CF, et al. Disposition of irinotecan and SN-38 following oral and intravenous irinotecan dosing in mice. Cancer Chemother Pharmacol. 1997;40(3):259-65. Chemical & Physical Properties Density 1.5±0.1 g/cm3 Boiling Point 810.3±65.0 °C at 760 mmHg Melting Point 217 °C Molecular Formula C22H20N2O5 Molecular Weight 392.405 Flash Point 443.8±34.3 °C Exact Mass 392.137207 PSA 101.65000 LogP 2.31 Vapour Pressure 0.0±3.0 mmHg at 25°C Index of Refraction 1.738 InChIKey FJHBVJOVLFPMQE-QFIPXVFZSA-N SMILES CCc1c2c(nc3ccc(O)cc13)-c1cc3c(c(=O)n1C2)COC(=O)C3(O)CC Storage condition −20°C |
| Use of | SN-38 is an active metabolite of the Topoisomerase I inhibitor Irinotecan. SN-38 inhibits DNA and RNA synthesis with IC50s of 0.077 and 1.3 μM, respectively. Properties Articles136 Name 7-Ethyl-10-hydroxycamptothecin Synonym More Synonyms 7-Ethyl-10-hydroxycamptothecin Biological Activity Description SN-38 is an active metabolite of the Topoisomerase I inhibitor Irinotecan. SN-38 inhibits DNA and RNA synthesis with IC50s of 0.077 and 1.3 μM, respectively. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase Research Areas >> Cancer Topoisomerase I References [1]. Wallin A, et al. Anticancer effect of SN-38 on colon cancer cell lines with different metastatic potential. Oncol Rep. 2008 Jun;19(6):1493-8. [2]. Jensen NF, et al. Characterization of DNA topoisomerase I in three SN-38 resistant human colon cancer cell lines reveals a newpair of resistance-associated mutations. J Exp Clin Cancer Res. 2016 Mar 31;35:56. [3]. Stewart CF, et al. Disposition of irinotecan and SN-38 following oral and intravenous irinotecan dosing in mice. Cancer Chemother Pharmacol. 1997;40(3):259-65. Chemical & Physical Properties Molecular Formula C22H20N2O5 Exact Mass 392.137207 PSA 101.65000 Index of Refraction 1.738 InChIKey FJHBVJOVLFPMQE-QFIPXVFZSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information United Nations classification: Item 1 Poisons. UN number: 1544 Formal shipping name: Alkaloid, solid, not otherwise specified Packing grade: III |
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