10-Hydroxycamptothecin Chemical Properties

Melting point:

230-237°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 

DMSO: ≥ 37.5 mg/mL (102.92 mM)

pka

8.93±0.40(Predicted)

form 

Pale yellow powder

color 

Yellow

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

InChIKey

LCZZWLIDINBPRC-FQEVSTJZSA-N

SMILES

N1C2C(=CC(O)=CC=2)C=C2CN3C(C=12)=CC1C(CC)(O)C(=O)OCC=1C3=O

CAS DataBase Reference

64439-81-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-25

Safety Statements 

26-36-45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

RTECS 

UQ0491000

MSDS

• Language:English Provider:SigmaAldrich

10-Hydroxycamptothecin Usage And Synthesis

Structure

The 10-Hydroxycamptothecin (10-HCPT) contains a lactone ring structure, which is key in keeping its anticancer activity. When the ring is hydrolyzed and opened, the activity of the 10-HCPT will be significantly reduced or inactivated. The stability of the ring structure of the lactone in the 10-HCPT is strongly related to the pH value. The structure of the lactone ring will be a closed loop when the pH value is less than 5, and the activity of 10-HCPT can be enhanced. When the pH value exceeds 7.4, the lactone ring will be broken, and the hydroxyl lactone will be inactivated. Accordingly, 10-HCPT has poor stability and low aqueous solubility. Nevertheless, previous reports have indicated that the water solubility and stability of 10-HCPT can be improved by complexation with liposomes. Furthermore, the delivery system of the liposome can increase the treatment efficacy of drugs by decreasing renal clearance and prolonging blood circulation[2].

Description

10-Hydroxycamptothecin: An Inhibitor of Topoisomerase I with Antitumor Activity
10-hydroxycamptothecin (10-HCPT) is an inhibitor of topoisomerase I originally isolated from the Chinese tree C. acuminata. 10-HCPT, a member of the camptothecin family, interferes with DNA synthesis by inhibiting the enzyme topoisomerase-I and has a broad spectrum of antitumor activity and less toxicity as camptothecins. However, 10-HCPT is insoluble in both water and physiological acceptable organic solvents and tends to change into its carboxylate form, which shows minimal antitumor activity and several unpredictable side effects. Therefore, appropriate drug delivery systems (DDS) for 10-HPCT have been developed to improve the stability of its lactone form. 10-HCPT is also an important precursor for the synthesis of clinically useful anticancer agents, such as irinotecan[1].

Chemical Properties

mp 268-270°C loss on drying <1%

Uses

therapeutic effects for liver cancer, stomach, and neck cancer and leukemia.

Uses

Topoisomerase inhibitor

Clinical Use

10-Hydroxycamptothecin (10-HCPT), a natural alkaloid derived from camptothecin analogues, has been successfully used to treat various tumors in the clinic, like liver cancer, colorectal cancer, lung cancer, and leukemia. The action of the 10-HCPT on cancer is similar to that of CPT, while the 10-HCPT is safer than CPT. The 10-HCPT can inhibit the DNA synthesis phase by acting on topoisomerase I, suppressing DNA replication and RNA synthesis[2].

References

[1] Chunjian Zhao. “Determination of Camptothecin and 10-Hydroxycamptothecin in Camptotheca acuminata by LC-ESI-MS/MS.” Analytical Letters 6 1 (2010): 2681–2693.
[2] Ruonan Shuang. “Pharmacokinetics of 10-hydroxycamptothecin–tetrandrine liposome complexes in rat by a simple and sensitive ultra-high performance liquid chromatography with tandem mass spectrometry.” Journal of separation science 43 3 (2019): 569–576.

10-Hydroxycamptothecin(64439-81-2)Related Product Information

• 10-HYDROXYCAMPTOTHECIN
• 7-Ethyl-10-hydroxycamptothecin
• (+)-Camptothecin
• 10-Hydroxycamptothecin
• Hydroxyl camptothecine
• Irinotecan hydrochloride
• Topotecan hydrochloride
• Camtobell hydrochloride
• Topotecan
• Lurtotecan
• RUBITECAN
• Exatecan
• CAMPTOTHECIN, [(G)3H]
• (S)-9-(4-METHYL-1-PIPERAZINYL)METHYL-10-HYDROXYCAMPTOTHECIN
• IRINOTECAN-D10 HYDROCHLORIDE
• SN-38 GLUCURONIDE
• 10-Hydroxycamptothecin
• 10-METHOXYCAMPTOTHECIN