345265-55-6

Usage

Synonym

BBR 3464

Chemical class

Anthraquinone-containing compound

Potential therapeutic applications

Anti-cancer properties
Anti-malarial properties

Mechanism of action (anti-cancer)

Induces DNA damage in cancer cells
Inhibits topoisomerase II, an enzyme involved in DNA replication and repair

Mechanism of action (anti-malarial)

Disrupts the function of parasite mitochondria

Current status

Subject of ongoing research for the development of novel treatments for cancer and malaria

Upstream product

• 110-85-0 piperazine 
• 82-34-8 1-nitroanthraquinone 
• 82-44-0 1-chloroanthracene-9,10-dione 
• 142-63-2 piperazine hexahydrate 

Relevant academic research and scientific papers

Hydrogen bonding and protonation effects in amino acids' anthraquinone derivatives - Spectroscopic and electrochemical studies

Six novel amino acid chromophores were synthesized and their spectroscopic, acid-base, and electrochemical properties are discussed in this work. In studied compounds, selected amino acid residues (L-Aspartic acid, L-Glutamic acid, L-Glutamine, L-Histidine, L-Lysine, L-Arginine) are attached to the 1-(piperazine) 9,10-anthraquinone skeleton via the amide bond between the carboxyl group of amino acid and nitrogen atom of the piperazine ring. All derivatives have been characterized using a variety of spectroscopic techniques (mass spectrometry, 1HNMR, UV–Vis, IR spectroscopy), acid-base (electrochemical and UV–Vis) titrations, and cyclic voltammetry methods. Basing on observed experimental effects, supported by quantum chemical simulations, the structure-properties links were established. They are indicative of the specific interactions within and/or in-between amino acid side groups, which are prone to form both, intra- and intermolecular hydrogen bonds as well as electrostatic interactions with the anthraquinone system.

Anthracene derivatives as anti-cancer agents

Use of compound of Formula (I): at least one of R1, R2, R5 and R6 is a group —AB and the others are independently selected from hydrogen, hydroxy, alkoxy or acyloxy, a group —AB a group -amino-(R7)nX—Y wherein R7 is a divalent organic radical and n is 0 or 1; R3 and R4are independently oxo, hydroxy or hydrogen; the or each A is independently a spacer group of formula -amino-(R7)n—X— which is bonded to the anthracene ring via the amino group nitrogen and to B via —X—, X is independently selected from O, NH and C(O); B is an amino acid residue or a peptide group or isostere thereof and Y is hydrogen or a capping group, or a physiologically acceptable derivative of such compound for the manufacture of a medicament for the treatment of cancers or microbial infections having cells exhibiting topoisomerase I activity characterised in that the group -amino-(R7)n—X— incorporates an optionally substituted heterocyclic ring directly attached to the anthroquinone ring through an amino nitrogen in the heterocycclic ring, or an optionally substituted heterocyclic or carbocyclic ring that is spaced from the anthraquinone ring by no more than an amino nitrogen and up to four carbon atoms.