9-hydroxyellipticine HClfeatured
WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#:406583
CAS#:52238-35-4 (HCl)
Description:9-hydroxyellipticine, also known asIGIG 929 and LS133324, is a potent cytotoxic and antitumor agent. Structurally, 9-hydroxyellipticine is a 9-hydroxy derivative of ellipticine. The hydroxy group in 9-hydroxyellipticines increases the apparent affinity for DNA, stabilisation of toposiomerase II-DNA cleavable complex, oxidation to reactive quinone-imine intermediates, phosphorylation of p53 suppressor proteins and cytotoxicity relative to the parent ellipticines.
Price and Availability
9-hydroxyellipticine, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.
Chemical Structure
Theoretical Analysis
MedKoo Cat#: 406583Name: 9-hydroxyellipticine HClCAS#: 52238-35-4 (HCl)Chemical Formula: C17H14N2OExact Mass: 262.11061Molecular Weight: 262.31Elemental Analysis:C, 68.34; H, 5.06; Cl, 11.87; N, 9.38; O, 5.35
Related CAS #:51131-85-2 (free base)52238-35-4 (HCl)58447-24-8 (methiodide).
Synonym:9-hydroxyellipticine HCl; 9-hydroxyellipticine hydrochloride; Hydroxyellipticine; 9-Hydroxyellipticin; NSC 210717;IGIG 929; IGIG929; IGIG-929; LS133324; LS-133324; LS 133324.
IUPAC/Chemical Name:5,11-dimethyl-6H-pyrido[4,3-b]carbazol-9-ol hydrochloride
InChi Key:DLDKVFOKLGPVBT-UHFFFAOYSA-N
InChi Code:InChI=1S/C17H14N2O.ClH/c1-9-14-8-18-6-5-12(14)10(2)17-16(9)13-7-11(20)3-4-15(13)19-17;/h3-8,19-20H,1-2H3;1H
SMILES Code:OC1=CC2=C(NC3=C2C(C)=C(C=NC=C4)C4=C3C)C=C1.[H]Cl
Technical Data
Additional Information
References
1: Harding MM, Grummitt AR. 9-hydroxyellipticine andderivatives as chemotherapy agents. Mini Rev Med Chem. 2003Mar;3(2):67-76. Review. PubMed PMID: 12570841.
2: Saeki K, Obi I, Ogiku N, Shigekawa M, Imagawa T, Matsumoto T.Cardioprotective effects of 9-hydroxyellipticine on ischemia andreperfusion in isolated rat heart. Jpn J Pharmacol. 2002 May;89(1):21-8.PubMed PMID: 12083739.
3: Sugikawa E, Tsunoda S, Nakanishi N, Ohashi M. 9-Hydroxyellipticinealters the conformation and DNA binding characteristics of mutated p53protein. Anticancer Res. 2001 Jul-Aug;21(4A):2671-5. PubMed PMID:11724337.
4: Mizumoto K, Sato N, Kusumoto M, Niiyama H, Maehara N, Nishio S, Li Z,Ogawa T, Tanaka M. Diverse effects of 9-hydroxyellipticine on thechemosensitivity of human pancreatic cancer cells harboring p53mutations. Cancer Lett. 2000 Feb 28;149(1-2):85-94. PubMed PMID:10737712.
5: Sugikawa E, Hosoi T, Yazaki N, Gamanuma M, Nakanishi N, Ohashi M.Mutant p53 mediated induction of cell cycle arrest and apoptosis at G1phase by 9-hydroxyellipticine. Anticancer Res. 1999Jul-Aug;19(4B):3099-108. PubMed PMID: 10652599.
6: Khélifa T, René B, Le Mée S, Lambert B, Saucier JM, Markovits J,Jacquemin-Sablon H, Jacquemin-Sablon A. Transfection of9-hydroxyellipticine-resistant Chinese hamster fibroblasts with humantopoisomerase IIalpha cDNA: selective restoration of the sensitivity toDNA religation inhibitors. Cancer Res. 1999 Oct 1;59(19):4927-36. PubMedPMID: 10519406.
7: Sato N, Mizumoto K, Kusumoto M, Niiyama H, Maehara N, Ogawa T, TanakaM. 9-Hydroxyellipticine inhibits telomerase activity in human pancreaticcancer cells. FEBS Lett. 1998 Dec 18;441(2):318-21. PubMed PMID:9883907.
8: Ismail MA, Sanders KJ, Fennell GC, Latham HC, Wormell P, Rodger A.Spectroscopic studies of 9-hydroxyellipticine binding to DNA.Biopolymers. 1998 Sep;46(3):127-43. PubMed PMID: 9741963.
9: Elcock AH, Rodger A, Richards WG. Theoretical studies of theintercalation of 9-hydroxyellipticine in DNA. Biopolymers. 1996Sep;39(3):309-26. PubMed PMID: 8756512.
10: Ohashi M, Sugikawa E, Nakanishi N. Inhibition of p53 proteinphosphorylation by 9-hydroxyellipticine: a possible anticancermechanism. Jpn J Cancer Res. 1995 Sep;86(9):819-27. PubMed PMID:7591958.