Interaction of oligonucleotides with benzo[c]phenanthridine alkaloid sanguilutine

Abstract

Benzo[c]phenanthridine alkaloid sanguilutine was extracted and purified from the dried roots of Sanguinaria canadensis. The interaction of the positively charged iminium form of alkaloid with double-stranded DNA oligonucleotides was studied using luminescence spectroscopy. The results showed that the interaction with various double-stranded oligonucleotides was not specific to A-T or G-C base pairs; also, no preference was found for either homogeneous or heterogeneous base composition of strands. The association constants were calculated to be in the range of (1.31–14.36) × 105 M−1. The luminescence intensity response at 610 nm to low concentrations of double-stranded DNA was found to be linear and can potentially be used for the fluorometric quantification of DNA. The limit of detection was estimated to be 120 ng mL−1 of DNA (calculated by 3σ method).

Influence of Solvent Polarity and DNA-Binding on Spectral Properties of Quaternary Benzo[c]phenanthridine Alkaloids

“…All studied alkaloids were isolated from plant material as published earlier [ 25 ] and were obtained as chloride salts of at least 93% purity. Stock solutions were prepared by dilution in MilliQ water (Millipore, USA) and were stored at room temperature in the dark.…”

Naturally occurring quaternary benzo[c]phenanthridine alkaloids selectively stabilize G-quadruplexes

“…QBAs are present in plants from families Fumariaceae, Papaveraceae, Ranunculaceae and Rutaceae. In addition to relatively common alkaloids such as sanguinarine and chelerythrine, other less common alkaloids such as sanguilutine, macarpine, sanguirubine or chelirubine have been extracted (Figure 1 and S1) 1 . Some of these have proven antiproliferative effects on skin melanoma cells.…”

“…7 In the case of chelirubine and sanguirubine, antimicrobial, anti-parasitic and anticancer effects have been demonstrated. 8,9 Besides these various biological effects on cells 2, 10 , QBA's in their iminium form were reported to interact with double stranded DNA (dsDNA) with a relatively weak mode 1,11 and comparable to that of ethidium bromide 12 . This interaction leads to changes in their fluorescent properties.…”

Seasonal variation in alkaloid composition and antiproliferative activity of Stylophorum lasiocarpum (Oliv.) Fedde

“…These properties of QBAs indicate their prospective applications in the treatment of resistant tumours. In addition to these biological effects on cells, QBAs in the quaternary form have been reported as interacting with dsDNA and Gquadruplexes (Rybáková et al, 2013). Currently, the targeting of quadruplexes by small molecules seeks to elucidate the biological effects and plays an interesting role in the development of new potential anti-cancer drugs (Galezowska et al, 2012).…”