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 as IGIG 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.
MedKoo Cat#: 406583
Name: 9-hydroxyellipticine HCl
CAS#: 52238-35-4 (HCl)
Chemical Formula: C17H14N2O
Exact Mass: 262.11061
Molecular Weight: 262.31
Elemental 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
Appearance: Solid powder
Purity: >98% (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
The following data is based on the product molecular weight 262.31 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.
| 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 |
1: Harding MM, Grummitt AR. 9-hydroxyellipticine and derivatives as chemotherapy agents. Mini Rev Med Chem. 2003 Mar;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 and reperfusion 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-Hydroxyellipticine alters the conformation and DNA binding characteristics of mutated p53 protein. 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 the chemosensitivity of human pancreatic cancer cells harboring p53 mutations. 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 G1 phase by 9-hydroxyellipticine. Anticancer Res. 1999 Jul-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 of 9-hydroxyellipticine-resistant Chinese hamster fibroblasts with human topoisomerase IIalpha cDNA: selective restoration of the sensitivity to DNA religation inhibitors. Cancer Res. 1999 Oct 1;59(19):4927-36. PubMed PMID: 10519406.
7: Sato N, Mizumoto K, Kusumoto M, Niiyama H, Maehara N, Ogawa T, Tanaka M. 9-Hydroxyellipticine inhibits telomerase activity in human pancreatic cancer 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 the intercalation of 9-hydroxyellipticine in DNA. Biopolymers. 1996 Sep;39(3):309-26. PubMed PMID: 8756512.
10: Ohashi M, Sugikawa E, Nakanishi N. Inhibition of p53 protein phosphorylation by 9-hydroxyellipticine: a possible anticancer mechanism. Jpn J Cancer Res. 1995 Sep;86(9):819-27. PubMed PMID: 7591958.
