9-Hydroxyellipticin free base

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MedKoo CAT#: 407424

CAS#: 51131-85-2 (free base)

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.

Chemical Structure

9-Hydroxyellipticin free base
CAS# 51131-85-2 (free base)

Theoretical Analysis

MedKoo Cat#: 407424
Name: 9-Hydroxyellipticin free base
CAS#: 51131-85-2 (free base)
Chemical Formula: C17H14N2O
Exact Mass: 262.1106
Molecular Weight: 262.312
Elemental Analysis: C, 77.84; H, 5.38; N, 10.68; O, 6.10

Price and Availability

Size Price Availability Quantity
100.0mg USD 1050.0 2 Weeks
200.0mg USD 1850.0 2 Weeks
500.0mg USD 3250.0 2 Weeks
1.0g USD 5250.0 2 Weeks
2.0g USD 8450.0 2 Weeks
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Related CAS #: 51131-85-2 (free base)   52238-35-4 (HCl)   58447-24-8 (methiodide).  

Synonym: 9-hydroxyellipticine; 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


InChi Code: InChI=1S/C17H14N2O/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

SMILES Code: OC1=CC2=C(NC3=C2C(C)=C(C=NC=C4)C4=C3C)C=C1

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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 262.312 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

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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.