The phenanthridine biguanides efficiently differentiate between dGdC, dAdT and rArU sequences by two independent, sensitive spectroscopic methods

Radić Stojković, Marijana; Miljanić, Snežana; Mišković, Katarina; Glavaš-Obrovac, Ljubica; Piantanida, Ivo (2011) The phenanthridine biguanides efficiently differentiate between dGdC, dAdT and rArU sequences by two independent, sensitive spectroscopic methods. Molecular biosystems, 7 (5). pp. 1753-1765. ISSN 1742-206X

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/2011...

Abstract

At submicromolar concentrations two novel phenanthridine biguanides exhibit distinctly different spectroscopic signals for dGdC and dAdT sequences, respectively, by opposite fluorimetric changes (quenching for dGdC and increase for dAdT) and especially bis-biguanide derivative gives opposite ICD response (negative ICD for dGC and strong positive for dAdT). This specific signalling was explained by ability of compounds to switch binding mode from intercalation into dGdC to minor groove binding into dAdT sequences. Both compounds bind to rArU by intercalation, yielding different fluorimetric and CD response in comparison to any of aforementioned ds-DNA. Moreover, both compounds revealed significantly higher affinity toward ds-polynucleotides in comparison to previously studied alkylamine- and urea-analogues. Furthermore, DNA/RNA binding properties of novel compounds could be controlled by pH, due to the protonation of heterocyclic nitrogen. Low in vitro cytotoxicity of both compounds against human cell lines makes them interesting spectrophotometric probes.

Item Type:

Article

Uncontrolled Keywords:

phenanthridine, biguanide, DNA, RNA

Subjects:

NATURAL SCIENCES > Chemistry

Divisions:

Division of Organic Chemistry and Biochemistry

Projects:

Project title	Project leader	Project code	Project type
Dizajn, sinteza i ispitivanje interakcija malih molekula s DNA, RNA i proteinima-	Ivo Piantanida	098-0982914-2918	MZOS
Spektroskopska analiza nezasićenih sustava i spojeva metala-	Snežana Miljanić	119-1191342-2959	MZOS
Mehanizam bioloških učinaka novih malih molekula na stanice tumora čovjeka-	Ljubica Glavaš Obrovac	219-0982914-2176	MZOS
Uloga malih zaštitinih TFF proteina u zdravlju i bolesti-	Tatjana Belovari	219-0982914-2179	MZOS