Definition
ChEBI: An aminoacridine that is acridine that is substituted by amino groups at positions 3 and 6. A slow-acting bacteriostat that is effective against many Gram-positive bacteria (but ineffective against spores), its salts were formerly used for treatment of bur
s and infected wounds.
Enzyme inhibitor
This dye (FWfree-base = 209.25 g/mol; CAS 92-62-6; orange-red solid; M.P. = 281 or 288°C; soluble in water; pKa = 9.65; solutions are light sensitive; insoluble in organic solvents such as benzene, diethyl ether, and chloroform), also known as proflavin and 3,6-acridinediamine, is a mutagen that intercalates in double-stranded DNA, inhibiting both DNA and RNA biosynthesis. Proflavine can also participate in the photooxidation of proteins (e.g., dopa decarboxylase. In addition, proflavine can inhibit a number of enzymes directly. For xample scriflavine, a mixture of proflavine with 3,6-diamino-10-methylacridinium chloride, inhibits protein kinase C. Target(s): L-amino-acid oxidase; carbonic anhydrase, or carbonate dehydratase, Ki ≈ 10 mM; chymotrypsin; DNA (cytosine-5-)-methyltransferase; DNA-directed RNA polymerase; dopa decarboxylase; F1Fo ATPase, or F1Fo ATP synthase, or H+-transporting two-sector ATPase; ficain, or ficin; glutamate decarboxylase; lysozyme; monoamine oxidase; NADH:cytochrome b5 reductase; nucleoside-triphosphatase, nuclear-envelope; papain; poly(ADP-ribose) glycohydrolase; polynucleotide adenylyltransferase, or poly(A) polymerase; pyruvate kinase; RNA-directed DNA polymerase; thrombin; tRNA adenylytltransferase; tRNA (guanine-N2-)-methyltransferase; tRNA cytidylyltransferase; tRNA methyltransferases; tRNA nucleotidyltransferase; and trypsin.
Purification Methods
Proclavine (3,6-diaminoacridine) [92-62-6] M 209.2, m 284-286o, pK 1 -2.7, pK 2 0 . 5 5 , pK 3 9.49. It crystallises from aqueous MeOH. The picrate crystallises from aqueous pyridine with m ~185o. [Beilstein 22 H 487, 22 I 649, 22 II 397, 22 III/IV 5487, 22/11 V 322.] For proflavin see 3,6-diaminoacridine hydrochloride.
