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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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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 titleProject leaderProject codeProject type
Dizajn, sinteza i ispitivanje interakcija malih molekula s DNA, RNA i proteinima-Ivo Piantanida098-0982914-2918MZOS
Spektroskopska analiza nezasićenih sustava i spojeva metala-Snežana Miljanić119-1191342-2959MZOS
Mehanizam bioloških učinaka novih malih molekula na stanice tumora čovjeka-Ljubica Glavaš Obrovac219-0982914-2176MZOS
Uloga malih zaštitinih TFF proteina u zdravlju i bolesti-Tatjana Belovari219-0982914-2179MZOS
Depositing User: Ivo Piantanida
Date Deposited: 20 Dec 2016 14:32
Last Modified: 20 Dec 2016 14:32
URI: http://fulir.irb.hr/id/eprint/1616
DOI: 10.1039/C1MB05030C

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