Acridine (Synonyms: 2,3,5,6-Dibenzopyridine, 10-Azaanthracene, Dibenzopyridine, NSC 3408)

Acridine is an azaarene.¹ It is a scaffold component of many pharmacologically active compounds, including topoisomerase inhibitors and DNA intercalators, as well as compounds with anticancer and antimalarial activities.^2,3,4,5 Acridine is also the backbone of some fluorescent probes, such as acridine orange and ICAAc .^6,7 It is genotoxic to bacteria when used at a concentration of 50 µg/ml.¹

1.Skarek, M., Cupr, P., RÉblova, K., et al.Assessment of toxic and genotoxic effects of N-heterocyclic polyaromatic hydrocarbons with miniaturized in vitro screening bioassays1-4() 2.Nelson, E.M., Tewey, K.M., and Liu, L.F.Mechanism of antitumor drug action: Poisoning of mammalian DNA topoisomerase II on DNA by 4’-(9-acridinylamino)-methanesulfon-m-anisidideProc. Natl. Acad. Sci. USA81(5)1361-1365(1984) 3.Fukui, K., Tanaka, K., Fujitsuka, M., et al.Distance dpendence of electron transfer in acridine-intercalated DNAJ. Photochem. Photobiol. B Biol.5018-27(1999) 4.Heald, R.A., Modi, C., Cookson, J.C., et al.Antitumor polycyclic acridines. 8.1 Synthesis and telomerase-inhibitory activity of methylated pentacyclic acridinium saltsJ. Med. Chem.45(3)590-597(2002) 5.Kumar, R., Kaur, M., and Kumari, M.Acridine: A versatile heterocyclic nucleusActa Pol. Pharm.69(1)3-9(2012) 6.Han, J., and Burgess, K.Fluorescent indicators for intracellular pHChem. Revs.110(5)2709-2728(2010) 7.Nagy, M., Racz, D., Nagy, Z.L., et al.Amino-isocyanoacridines: Novel, tunable solvatochromic fluorophores as phystiological pH probesSci. Rep.98250(2019)