Collect. Czech. Chem. Commun. 2009, 74, 1081-1090
Published online 2009-07-15 10:43:38

Synthesis of unsymmetric cyanine dye via merocyanine and their interaction with DNA

Tomáš Břízaa,b,*, Zdeněk Kejíkb, Jarmila Královác, Pavel Martásekb and Vladimír Krála,d

a Department of Analytical Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
b First Faculty of Medicine, Charles University, Kateřinská 32, 121 08 Prague 2, Czech Republic
c Institute of Molecular Genetics, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
d Zentiva R & D, U Kabelovny 130, 102 37 Prague 10, Czech Republic


An effective method has been developed for synthesis of neutral merocyanine dye 4 from (4-nitrophenyl)malondialdehyde. Merocyanine 4 was used as a basic building block for preparation of unsymmetric cyanine dyes 9 and 10, both derived from the same aromatic malondialdehyde. With the cyanine 10, pH-dependent affinity to DNA has been studied. Unsymmetric cyanine dye 10 has been compared with symmetric dye 8. The corresponding binding constants (K) have been calculated for various pH.

Keywords: Malondialdehyde; Merocyanine; Symmetric; Unsymmetric; Cyanine; DNA.

References: 12 live references.