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(S)-10-Hydroxycamptothecin inhibitor of topoisomerase I

(S)-10-Hydroxycamptothecin

Catalog No. BCN1225
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20mg $70 In stock
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Quality Control of (S)-10-Hydroxycamptothecin

Chemical structure

(S)-10-Hydroxycamptothecin

Biological Activity of (S)-10-Hydroxycamptothecin

1. 10-Hydroxycamptothecin-loaded SLN suggested being a promising vehicle for liver-targeted drug delivery.
2. Encapsulated 10-Hydroxycamptothecin to regain its anti-cancer activity following selective internalization of the complex into carcinoma cells ,via integrin receptor mediated endocytosis.

(S)-10-Hydroxycamptothecin Dilution Calculator

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Chemical Properties of (S)-10-Hydroxycamptothecin

Cas No. 19685-09-7 SDF Download SDF
SMILES CC[C@@]1(O)C(=O)OCC2=C1C=C3N(Cc4cc5cc(O)ccc5nc34)C2=O
Standard InChIKey HAWSQZCWOQZXHI-FQEVSTJZSA-N
Standard 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
Type of Compound Alkaloids Appearance Powder
Formula C20H16N2O5 M.Wt 364.35
Solubility Soluble in DMSO > 10 mM
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other courier with RT , or blue ice upon request.

Preparing Stock Solutions of (S)-10-Hydroxycamptothecin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7446 mL 13.7231 mL 27.4461 mL 54.8923 mL 68.6153 mL
5 mM 0.5489 mL 2.7446 mL 5.4892 mL 10.9785 mL 13.7231 mL
10 mM 0.2745 mL 1.3723 mL 2.7446 mL 5.4892 mL 6.8615 mL
50 mM 0.0549 mL 0.2745 mL 0.5489 mL 1.0978 mL 1.3723 mL
100 mM 0.0274 mL 0.1372 mL 0.2745 mL 0.5489 mL 0.6862 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

Preparation of (S)-10-Hydroxycamptothecin

This product is isolated and purified from the barks of Camptotheca acuminata Decne

Background on (S)-10-Hydroxycamptothecin

IC50: 0.31 μM

10-Hydroxycamptothecin is a dose-dependent growth inhibitor of human microvascular endothelial cells (HMEC), and significantly inhibits the migration of HMEC with IC50 of 0.63 μM, resulting in a dose-dependent inhibition of tube formation with IC50 of 0.96 μM [1,2].

An antiangiogenic strategy may be effective as an anticancer therapy, because the growth and metastasis of solid tumors depend on the development of an adequate blood supply via angiogenesis [1,2].

In vitro: The proliferation of human microvascular endothelial cells (HMEC) and seven human tumor cell lines were detected by SRB assay, resulting in study the antiangiogenic potential of 10-hydroxycamptothecin (HCPT), ,and the endothelial cell migration and tube formation were assessed using two in vitro model systems[2].

In vivo: Using a modification of the chick embryo chorioallantoic membrane (CAM) assay defines inhibition of angiogenesis in vivo. Morphological assessment of apoptosis was performed by fluorescence microscope. HCPT 0.313-5 μmol/L treatment was in a dose-dependent inhibition of proliferation, migration and tube formation in HMEC cells, and HCPT 6.25-25 nmol/egg prevented angiogenesis in CAM assay. HCPT 1.25-5 μmol/L induced typical morphological changes of apoptosis (including condensed chromatin, nuclear fragmentation, and reduction in volume in HMEC cells). HCPT significantly blocked angiogenesis both in vitro and in vivo at relatively low concentrations, and this effect was connected with induction of apoptosis in HMEC cells. These results taken collectively reveal that HCPT may be a potential for antiangiogenetic and cytotoxic drug and further investigationis warranted [2,3].

Clinical trial: So far, no clinical study has been conducted.

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.

References on (S)-10-Hydroxycamptothecin

Intracellular target delivery of 10-hydroxycamptothecin with solid lipid nanoparticles against multidrug resistance.[Pubmed: 25766079]


The main objective of this study was to design a suitable drug delivery system for 10-Hydroxycamptothecin (HCPT). In this study, HCPT-loaded solid lipid nanoparticle (10-Hydroxycamptothecin-loaded SLN) was successfully prepared. The 10-Hydroxycamptothecin-loaded SLN was characterized by size, entrapment efficiency and drug release manner. The cytotoxicity of 10-Hydroxycamptothecin-loaded SLN was assessed in vitro using HepG2/10-Hydroxycamptothecin cells and in vivo utilizing human tumor xenograft nude mouse model. 10-Hydroxycamptothecin-loaded SLN indicated the ability to target HepG2/10-Hydroxycamptothecin cells and accumulated higher drug content in HepG2/10-Hydroxycamptothecin cells. 10-Hydroxycamptothecin-loaded SLN enhanced the cytotoxicity of 10-Hydroxycamptothecin in a concentration-dependent manner. Based on these results, HCPT-loaded SLN suggested being a promising vehicle for liver-targeted drug delivery. Moreover, it can be of clinical interest to overcome multidrug resistance (MDR) effectively.

A novel multifunctional poly(amidoamine) dendrimeric delivery system with superior encapsulation capacity for targeted delivery of the chemotherapy drug 10-hydroxycamptothecin.[Pubmed: 24530519]


With the aim of developing an efficient targeted delivery system for cancer therapy that overcomes drug leakage during circulation, we prepared a novel multifunctional dendrimeric carrier by integrating long hydrophobic C₁₂ alkyl chains, poly(ethylene glycol) chains and c(RGDfK) ligands presented on the surface. This dendrimer was able to tightly encapsulate the hydrophobic anticancer drug 10-Hydroxycamptothecin (10-HCPT) through simple complexation and selectively target the drug to cancer cells overexpressing integrin αvβ₃ through high affinity interactions. The complex has a high loading efficiency, with each molecule encapsulating approximately 20 drug molecules; high stability, without any detectable drug release during dialysis for three days; and high water solubility, achieving an approximately 600-fold increase over the water solubility of free 10-Hydroxycamptothecin. This complex exhibited notably high cytotoxicity against 22RV1 cells overexpressing integrin αvβ₃ and a far lower cytotoxicity against MCF-7 cells, which express low levels of integrin αvβ₃. We expected encapsulated 10-Hydroxycamptothecin to regain its anti-cancer activity following selective internalization of the complex into carcinoma cells via integrin receptor mediated endocytosis. As the drug remains inactive before internalization, this carrier has the ability to overcome problems associated with drug leakage in the circulation and off-target effects on normal tissues.

Synthesis of novel 10-hydroxycamptothecin derivatives utilizing topotecan hydrochloride as ortho-quinonemethide precursor. [Pubmed: 25481395]


A series of 9-(alkylthiomethyl)-10-Hydroxycamptothecins and pyrano-fused camptothecin derivatives were synthesized via the reaction of topotecan hydrochloride with various thiols and alkyl vinyl ethers respectively. In the reactions, topotecan hydrochloride was utilized as ortho-quinonemethide (o-QM) precursor. The configuration of 19 was determined by (1)H NMR and NOESY spectra as syn-isomers, suggesting that the cycloaddition of topotecan with alkyl vinyl ethers could undergo a hetero Diels-Alder reaction. All the synthesized compounds were screened on cancer cell lines HepG2, KB, HCT-8 and SGC7901. Some compounds were selected to assess their inhibitory activity against Topo I via Topo I mediated DNA cleavage assays. The results showed that among those tested 9-(alkylthiomethyl)-10-Hydroxycamptothecins, the compounds with bulkier hydrophobic side chains at 9-position have better bioactivities. As well as all pyrano-fused camptothecins possess antiproliferative activity against the tested cancer cell lines. Docking studies suggested that there are more interactions between the novel analogues and the binding site of Topo I.

A simple HPLC method with fluorescence detection for simultaneous determination of 10-methoxycamptothecin and its metabolite 10-hydroxycamptothecin in rat liver tissue.[Pubmed: 24782285]


A simple HPLC method to determine the amount of 10-methoxycamptothecin (MCPT) and its major metabolite 10-Hydroxycamptothecin (HCPT) in rat liver tissue was developed in the present study. Camptothecin (CPT) was used as internal standard (IS). A piecewise linear function was used over lower and higher concentrations, respectively. The calibration curves were linear (r (2) >0.99) over concentrations from 2.5 to 20 ng/mL and 20 to 320 ng/mL for both MCPT and 10-Hydroxycamptothecin . The method had an accuracy of 92.74% to 112.76%, and the intra- and inter-day precision (RSD%) were 11.85% or less for MCPT and 10-Hydroxycamptothecin . The stability data showed no significant degradation occurred under the experimental conditions. This method was successfully applied to the tissue distribution study of MCPT and its metabolite 10-Hydroxycamptothecin in liver tissue samples after intravenous administration.

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(S)-10-Hydroxycamptothecin ,19685-09-7,DNA Damage/DNA Repair,Topoisomerase, supplier, inhibitor,Antagonist,Blocker,Modulator,Agonist, activators, activates, potent, BioCrick

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