10-Hydroxycamptothecin
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MedKoo CAT#: 406281

CAS#: 19685-09-7

Description: 10-Hydroxycamptothecin (10-HCPT), an indole alkaloid isolated from a Chinese tree, Camptotheca acuminate, inhibits the activity of topoisomerase I and has a broad spectrum of anticancer activity in vitro and in vivo.


Chemical Structure

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10-Hydroxycamptothecin
CAS# 19685-09-7

Theoretical Analysis

MedKoo Cat#: 406281
Name: 10-Hydroxycamptothecin
CAS#: 19685-09-7
Chemical Formula: C20H16N2O5
Exact Mass: 364.10592
Molecular Weight: 364.35
Elemental Analysis: C, 65.93; H, 4.43; N, 7.69; O, 21.96

Price and Availability

Size Price Availability Quantity
200.0mg USD 150.0 Same day
1.0g USD 450.0 Same day
2.0g USD 750.0 Same day
10.0g USD 1650.0 2 weeks
20.0g USD 2650.0 2 weeks
100.0g USD 4250.0 2 weeks
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Synonym: 10-HCPT; 10-OHCPT; Hydroxycamptothecin; 10-hydroxycamptothecine; (S)-10-Hydroxycamptothecin; NSC 107124; NSC-107124; NSC107124;

IUPAC/Chemical Name: (S)-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

InChi Key: HAWSQZCWOQZXHI-FQEVSTJZSA-N

InChi Code: 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

SMILES Code: O=C1[C@](O)(CC)C2=C(CO1)C(N3CC4=CC5=CC(O)=CC=C5N=C4C3=C2)=O

Appearance: Light yellow solid powder

Purity: >97% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: (S)-10-Hydroxycamptothecin (10-HCPT;10-Hydroxycampto thecin) is a DNA topoisomerase I inhibitor of isolated from the Chinese plant Camptotheca accuminata
In vitro activity: To verify the role of miR-23b-3p in HCPT-induced fibroblast apoptosis, human fibroblasts were transfected with Lv-miR-23b-3p and Lv-anti-miR-23b-3p, followed by co-treatment with HCPT. TUNEL assays revealed that miR-23b-3p increased HCPT-induced fibroblast apoptosis (Fig. 4A). Flow cytometric analysis confirmed the TUNEL assay results; HCPT treatment increased the fibroblast apoptotic rate compare to the control group, and transfection with Lv-anti-miR-23b-3p partially reversed the increased apoptosis caused by HCPT, whereas transfection with Lv-miR-23b-3p significantly increased cell apoptosis caused by HCPT (Fig. 4B). Consistent with these apoptosis data, treatment with HCPT alone or with Lv-miR-23b-3p co-transfection increased the expression of apoptosis-related proteins cleaved-PARP and BAX, and decreased the expression of Bcl-2, compared with the Control group (Fig. 4C). Transfecting Lv-anti-miR-23b-3p into the fibroblasts partially attenuated the HCPT-induced increased expression of these proteins. These data indicated that upregulation of miR-23b-3p expression by HCPT treatment increases human fibroblast apoptosis. Reference: Mol Med Rep. 2019 Apr; 19(4): 2680–2686. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6423607/
In vivo activity: To examine the possible inhibitory effects of HCPT on PDX tumor growth, patient-derived LEG104 and LEG110 ESCC tumors with high expression levels of TOP I were adopted in this investigation. The treatment of PDX tumors grown in mice with HCPT (4 mg/kg and 8 mg/kg body weight) decreased the tumor volume and tumor weight significantly (Figure 5A–D). The weight and size of tumors were also dramatically decreased after HCPT administration for 18 or 29 days (Figure 5B,C,E,F). While eliciting antitumor activity in PDX tumor-bearing mice, HCPT application did not exhibit any remarkable signs of toxicity in mice (Figure S3). The IHC and HE staining of the PDX tumor sections showed more regression of tumor cells and changes in morphology, such as cell enlargement, caryolysis, variable nucleus size, nuclear pyknosis, and nucleolar margin blurring in the treatment group in comparison with the vehicle group (Figure 5G). Darker staining in the cytoplasm by eosin in the HCPT-treated groups indicated apoptosis phenomenon which was not evident in the vehicle group (Figure 5G). Moreover, there was a significant decrease in the expression of Ki-67 and elevation in cleaved caspase-3, which indicated that the cell proliferation was inhibited and apoptosis was induced after HCPT application. The IHC analysis of HCPT-treated tumors also showed decreased TOP I expression and increased phosphorylated rH2A.X level (Figure 5G,H, Figure S4). These findings mean that TOP I appears to be a valid therapeutic target and HCPT may be considered for further clinical application in ESCC. Reference: Cancers (Basel). 2019 Dec; 11(12): 1964. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6966462

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 2.0 5.49
DMF 2.0 5.49

Preparing Stock Solutions

The following data is based on the product molecular weight 364.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Zeng L, Sun Y, Li X, Wang J, Yan L. 10‑Hydroxycamptothecin induces apoptosis in human fibroblasts by regulating miRNA‑23b‑3p expression. Mol Med Rep. 2019 Apr;19(4):2680-2686. doi: 10.3892/mmr.2019.9927. Epub 2019 Feb 1. PMID: 30720099; PMCID: PMC6423607. 2. Song M, Yin S, Zhao R, Liu K, Kundu JK, Shim JH, Lee MH, Dong Z. (S)-10-Hydroxycamptothecin Inhibits Esophageal Squamous Cell Carcinoma Growth In Vitro and In Vivo Via Decreasing Topoisomerase I Enzyme Activity. Cancers (Basel). 2019 Dec 6;11(12):1964. doi: 10.3390/cancers11121964. PMID: 31817790; PMCID: PMC6966462. 3. Dai J, Sun Y, Yan L, Wang J, Li X, He J. Upregulation of NOXA by 10-Hydroxycamptothecin plays a key role in inducing fibroblasts apoptosis and reducing epidural fibrosis. PeerJ. 2017 Jan 12;5:e2858. doi: 10.7717/peerj.2858. PMID: 28097065; PMCID: PMC5237371.
In vitro protocol: 1. Zeng L, Sun Y, Li X, Wang J, Yan L. 10‑Hydroxycamptothecin induces apoptosis in human fibroblasts by regulating miRNA‑23b‑3p expression. Mol Med Rep. 2019 Apr;19(4):2680-2686. doi: 10.3892/mmr.2019.9927. Epub 2019 Feb 1. PMID: 30720099; PMCID: PMC6423607. 2. Song M, Yin S, Zhao R, Liu K, Kundu JK, Shim JH, Lee MH, Dong Z. (S)-10-Hydroxycamptothecin Inhibits Esophageal Squamous Cell Carcinoma Growth In Vitro and In Vivo Via Decreasing Topoisomerase I Enzyme Activity. Cancers (Basel). 2019 Dec 6;11(12):1964. doi: 10.3390/cancers11121964. PMID: 31817790; PMCID: PMC6966462.
In vivo protocol: 1. Song M, Yin S, Zhao R, Liu K, Kundu JK, Shim JH, Lee MH, Dong Z. (S)-10-Hydroxycamptothecin Inhibits Esophageal Squamous Cell Carcinoma Growth In Vitro and In Vivo Via Decreasing Topoisomerase I Enzyme Activity. Cancers (Basel). 2019 Dec 6;11(12):1964. doi: 10.3390/cancers11121964. PMID: 31817790; PMCID: PMC6966462. 2. Dai J, Sun Y, Yan L, Wang J, Li X, He J. Upregulation of NOXA by 10-Hydroxycamptothecin plays a key role in inducing fibroblasts apoptosis and reducing epidural fibrosis. PeerJ. 2017 Jan 12;5:e2858. doi: 10.7717/peerj.2858. PMID: 28097065; PMCID: PMC5237371.

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1: Liu M, Chen D, Wang C, Chen X, Wen Z, Cao Y, He H. Intracellular target delivery of 10-hydroxycamptothecin with solid lipid nanoparticles against multidrug resistance. J Drug Target. 2015 Mar 13:1-6. [Epub ahead of print] PubMed PMID: 25766079.

2: Bian Z, Yu Y, Quan C, Guan R, Jin Y, Wu J, Xu L, Chen F, Bai J, Sun W, Fu S. RPL13A as a reference gene for normalizing mRNA transcription of ovarian cancer cells with paclitaxel and 10-hydroxycamptothecin treatments. Mol Med Rep. 2015 Apr;11(4):3188-94. doi: 10.3892/mmr.2014.3108. Epub 2014 Dec 17. PubMed PMID: 25523336.

3: Tan H, Wang G, Li J, Meng G, Liu Z, Dong M, Li Y, Ju D, Zhang Q. Synthesis of novel 10-hydroxycamptothecin derivatives utilizing topotecan hydrochloride as ortho-quinonemethide precursor. Bioorg Med Chem. 2015 Jan 1;23(1):118-25. doi: 10.1016/j.bmc.2014.11.020. Epub 2014 Nov 20. PubMed PMID: 25481395.

4: Zhou M, Liu M, He X, Yu H, Wu D, Yao Y, Fan S, Zhang P, Shi W, Zhong B. Synthesis and biological evaluation of novel 10-substituted-7-ethyl-10-hydroxycamptothecin (SN-38) prodrugs. Molecules. 2014 Nov 27;19(12):19718-31. doi: 10.3390/molecules191219718. PubMed PMID: 25438082.

5: Xu P, Chen DS, Xi J, Yao ZJ. Short Protecting Group-free Syntheses of Camptothecin and 10-Hydroxycamptothecin Using Cascade Methodologies. Chem Asian J. 2014 Nov 27. doi: 10.1002/asia.201403190. [Epub ahead of print] PubMed PMID: 25431030.

6: Lü Y, Yang LF, Dong N. [Studies on the effects of cucurbit (n = 7) uril on the physicohemical properties and anticancer activity of 10-hydroxycamptothecin]. Guang Pu Xue Yu Guang Pu Fen Xi. 2014 Jun;34(6):1610-4. Chinese. PubMed PMID: 25358173.

7: Yang FY, Zhang WP, Wang XY, Yang WC, Dang HW. [Pharmacokinetics of SN-38 in rats and tissue distribution of 7-ethyl-10-hydroxycamptothecin in mice after intravenous injection of irinotecan hydrochloride nanoparticles]. Yao Xue Xue Bao. 2014 Jul;49(7):1029-33. Chinese. PubMed PMID: 25233635.

8: Sepehri N, Rouhani H, Ghanbarpour AR, Gharghabi M, Tavassolian F, Amini M, Ostad SN, Ghahremani MH, Dinarvand R. Human serum albumin conjugates of 7-ethyl-10-hydroxycamptothecin (SN38) for cancer treatment. Biomed Res Int. 2014;2014:963507. doi: 10.1155/2014/963507. Epub 2014 May 7. PubMed PMID: 24895635; PubMed Central PMCID: PMC4033423.

9: Liu Y, Shao C, Fan B, Li S, Wang Y, Zheng J. A Simple HPLC Method with Fluorescence Detection for Simultaneous Determination of 10-methoxycamptothecin and its Metabolite 10-hydroxycamptothecin in Rat Liver Tissue. Drug Res (Stuttg). 2015 Mar;65(3):147-52. doi: 10.1055/s-0034-1374635. Epub 2014 Apr 29. PubMed PMID: 24782285.

10: Liu J, Liu J, Chu L, Zhang Y, Xu H, Kong D, Yang Z, Yang C, Ding D. Self-assembling peptide of D-amino acids boosts selectivity and antitumor efficacy of 10-hydroxycamptothecin. ACS Appl Mater Interfaces. 2014 Apr 23;6(8):5558-65. doi: 10.1021/am406007g. Epub 2014 Apr 2. PubMed PMID: 24660962.