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Names | |
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Preferred IUPAC name 5,11-Dimethyl-6H-pyrido[4,3-b]carbazole | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.007.514 |
EC Number |
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KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C17H14N2 | |
Molar mass | 246.313 g·mol−1 |
Appearance | Yellow crystalline powder [1] |
Density | 1.257±0.06 g/cm3 [2] |
Melting point | 316–318 °C (601–604 °F; 589–591 K) [2] |
Very low [3] | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | toxic |
GHS labelling: | |
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H301 [4] | |
P264, P270, P301+P310, P321, P330, P405, P501 [4] | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Ellipticine is a tetracyclic alkaloid first extracted from the tree species Ochrosia elliptica and Rauvolfia sandwicensis [5] [6] which inhibits the enzyme topoisomerase II via intercalative binding to DNA. [7]
Ellipticine is an organic compound present in several trees within the genera Ochrosia , Rauvolfia , and Aspidosperma . [8] It was first isolated from Ochrosia elliptica Labill. , a flowering tree native to Australia and New Caledonia which gives the alkaloid its name, in 1959, [5] and synthesised by Robert Burns Woodward later the same year. [6]
Ellipticine is a known intercalator, capable of entering a DNA strand between base pairs. In its intercalated state, ellipticine binds strongly [9] and lies parallel to the base pairs, [10] increasing the superhelical density of the DNA. [11] Intercalated ellipticine binds directly to topoisomerase II, an enzyme involved in DNA replication, [12] inhibiting the enzyme and resulting in powerful antitumour activity. [10] In clinical trials, ellipticine derivatives have been observed to induce remission of tumour growth, but are not used for medical purposes due to their high toxicity; side effects include nausea and vomiting, hypertension, cramp, pronounced fatigue, mouth dryness, and mycosis of the tongue and oesophagus. [13]
Further DNA damage results from the formation of covalent DNA adducts following enzymatic activation of ellipticine by with cytochromes P450 and peroxidases, meaning that ellipticine is classified as a prodrug. [14]
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