Introduction：Basic information about 10-Hydroxycamptothecin CAS 19685-09-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
10-Hydroxycamptothecin Basic information
| Product Name: | 10-Hydroxycamptothecin |
| Synonyms: | Camptothecae Acuminatae extract;hydrate,(s)-dihydroxy;hydroxy-camptotheci;Hydroxycamptothencine;(20S)-10-HYDROXYCAMPTOTHECIN 98%;(20S)-10-Hydroxycamptothecin;HYDROCAMPTOTHECINE;CAMPTOTHECIN, 10-HYDROXY(SH) |
| CAS: | 19685-09-7 |
| MF: | C20H16N2O5 |
| MW: | 364.35 |
| EINECS: | 805-668-4 |
| Product Categories: | Inhibitors;natural product;Alkaloids;INTERMEDIATESOFIRINOTECANHCLTRIHYDRATE;Camptothecin series;Natural Plant Extract;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Natural Anti-cancer Medical Materials and It's Derivatives |
| Mol File: | 19685-09-7.mol |
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10-Hydroxycamptothecin Chemical Properties
| Melting point | 265-270°C |
| Boiling point | 820.7±65.0 °C(Predicted) |
| density | 1.60 |
| storage temp. | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| solubility | ≥23.8 mg/mL in DMSO with gentle warming; insoluble in EtOH; insoluble in H2O |
| form | powder to crystal |
| pka | 8.93±0.40(Predicted) |
| color | White to Yellow to Orange |
| InChI | InChI=1S/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-6-12(23)3-4-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3/t20-/m0/s1 |
| InChIKey | HAWSQZCWOQZXHI-FQEVSTJZSA-N |
| SMILES | N1C2C(=CC(O)=CC=2)C=C2CN3C(C=12)=CC1[C@](CC)(O)C(=O)OCC=1C3=O |
| CAS DataBase Reference | 19685-09-7(CAS DataBase Reference) |
Safety Information
| Safety Statements | 24/25 |
| HS Code | 29349990 |
10-Hydroxycamptothecin Usage And Synthesis
| Description | DNA topoisomerases relax supercoiled DNA during replication, transcription, recombination, repair, and chromosome condensation. The relaxation of DNA supercoiling by topoisomerase I at single-strand breaks represents a target for anticancer agents to intercalate between DNA base pairs, leading to the activation of apoptotic and cell cycle arrest pathways. (S)-10-hydroxy-Camptothecin is an inhibitor of topoisomerase I originally isolated from the Chinese tree C. acuminata. It is a member of the camptothecin family that demonstrates less toxicity than its parent compound. (S)-10-hydroxy-Camptothecin has strong anti-tumor activity against a wide range of experimental tumors including L1210 leukemia cells (IC50 = 1.15 μM). In vitro treatment of human HepG2 cells with 5-20 μM (S)-10-hydroxy-camptothecin results in cell cycle arrest at the G2/M phase. |
| Chemical Properties | Yellow Solid |
| Uses | A Camptothecin derivative; a topoisomerase inhibitor for cancer therapy |
| Definition | ChEBI: 10-Hydroxycamptothecin is a pyranoindolizinoquinoline. |
| in vitro | 10-Hydroxycamptothecin inhibited the growth of BT-20 and MDA-231 cells with IC50 of 34.3nM and 7.27nM, respectively, which was more potent than camptothecin (CPT) with IC50>500nM. 10-Hydroxycamptothecin potently induces the formation of the pBR322 plasmid DNA cleavage complex mediated by human topoisomerase I with an EC50 of 0.35 μM, more than 50-fold more potent than CPT with an EC50 of 18.85 μM. 10-Hydroxycamptothecin treatment caused dose-dependent growth inhibition of human microvascular endothelial cells (HMECs) with IC50 of 0.31 μM and significantly inhibited HMEC migration with IC50 of 0.63 μM. Treatment of HMEC cells with 10-Hydroxycamptothecin also inhibited microtubule formation in a dose-dependent manner with IC50 of 0.96 μM. 10-Hydroxycamptothecin (5-20 nM) significantly inhibits the differentiation of Colo205 cells, arrests the cell cycle in G2 phase, and induces apoptosis through a caspase-3-dependent pathway. |
| in vivo | In the CAM model, 10-Hydroxycamptothecin treatment inhibited angiogenesis in a concentration-dependent manner, with 95% inhibition at 25 nM, more potent than suramin, which inhibited only 60% of angiogenesis at 125 nM. 10-Hydroxycamptothecin, administered orally at low doses of 2.5-7.5 mg/kg every two days, caused significant growth inhibition in Colo205 xenograft mice, but no acute toxicity. LD50: 104 mg/kg in mice (intraperitoneal injection). |
| IC 50 | 0.31 μm |
| references | [1] vladu b, woynarowski jm, manikumar g, wani mc, wall me, von hoff dd, wadkins rm. 7- and 10-substituted camptothecins: dependence of topoisomerase i-dna cleavable complex formation and stability on the 7- and 10-substituents. mol pharmacol. 2000 feb;57(2):243-51.
[2] xiao d, tan w, li m, ding j. antiangiogenic potential of 10-hydroxycamptothecin. life sci. 2001 aug 24;69(14):1619-28.
[3] ping yh, lee hc, lee jy, wu ph, ho lk, chi cw, lu mf, wang jj. anticancer effects of low-dose 10-hydroxycamptothecin in human colon cancer. oncol rep. 2006 may;15(5):1273-9. |
10-Hydroxycamptothecin Preparation Products And Raw materials
| Preparation Products | TOPOTECANACETATE |
