Synthesis of an acridine orange sulfonamide derivative with potent carbonic anhydrase IX inhibitory action

Figures & data

Scheme 1. General synthetic procedure for 4-(2-((3,6-bis(dimethylamino)acridin-9-yl)amino)ethyl)benzenesulfonamide perchlorate 3 and N,N,N',N'-tetramethyl-N''-phenethyl-acridine-3,6,9-triamine 4.

Table 1. hCA I, II; IX and XII inhibition data with compounds 3, 4, AAZ and AO, by a stopped-flow CO₂ hydrase assay53.

	KI (nM)^a
Compound	hCA I	hCA II	hCA IX	hCA XII
3	7680	1650	9.1	4.9
4	>50,000	>50,000	>50,000	>50,000
AAZ	250	12	25.1	5.6
AO	>50,000	>50,000	>50,000	>50,000

^a Errors in the range of 5% of the reported values, from three different determinations (data not shown).

Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971;246:2561–73.

 PubMed Web of Science ®Google Scholar