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3 article(s) from Radić Stojković, Marijana

Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

Josipa Matić,
Tana Tandarić,
Marijana Radić Stojković,
Filip Šupljika,
Zrinka Karačić,
Ana Tomašić Paić,
Lucija Horvat,
Robert Vianello and
Lidija-Marija Tumir

Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40

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Scheme 1: Novel pyrene–phenanthridine conjugates Phen-Py-1 (longer, flexible linker) and Phen-Py-2 (shorter, ...

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Scheme 2: Synthesis of Phen-Py-1 and Phen-Py-2 by amide formation; Reagents and conditions: 1. TFA–H₂O mixtur...

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Figure 1: 2D (left) and 3D (right) representation of fluorescence emission spectra of Phen-Py-1 (c = 2 × 10⁻⁶...

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Figure 2: Most representative structures of the conjugates Phen-Py-1 and Phen-Py-2 at different pH conditions...

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Figure 3: UV–vis titration of Phen-Py-1 with ct-DNA,; changes in the UV–vis spectra of Phen-Py-1 at λ = 350 n...

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Figure 4: . Experimental (■) and calculated (–) (by Scatchard equation Table 2) fluorescence intensities of compound ...

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Figure 5: Comparison of spectra of DNA-dye complex (r = 0.5, black) and sum of DNA and dye spectra (red) of a...

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Figure 6: Fluorimetric titration of Phen-Py-1, λ_exc = 352 nm, c = 1 × 10⁻⁶ mol dm⁻³ with dipeptidyl peptidase...

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Figure 7: A: ITC titration: raw titration data from the experimental injections of human DPP III enzyme mutan...

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Published 26 Apr 2023

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Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

Lidija-Marija Tumir,
Marijana Radić Stojković and
Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

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Scheme 1: The Grignard-based synthesis of 6-alkyl phenanthridine.

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Scheme 2: Radical-mediated synthesis of 6-arylphenanthridine [14].

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Scheme 3: A t-BuO^• radical-assisted homolytic aromatic substitution mechanism proposed for the conversion of ...

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Scheme 4: Synthesis of 5,6-unsubstituted phenanthridine starting from 2-iodobenzyl chloride and aniline [17].

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Scheme 5: Phenanthridine synthesis initiated by UV-light irradiation photolysis of acetophenone O-ethoxycarbo...

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Scheme 6: PhI(OAc)₂-mediated oxidative cyclization of 2-isocyanobiphenyls with CF₃SiMe₃ [19,20].

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Scheme 7: Targeting 6-perfluoroalkylphenanthridines [21,22].

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Scheme 8: Easily accessible biphenyl isocyanides reacting under mild conditions (room temp., visible light ir...

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Scheme 9: Microwave irradiation of Diels–Alder adduct followed by UV irradiation of dihydrophenanthridines yi...

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Scheme 10: A representative palladium catalytic cycle.

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Scheme 11: The common Pd-catalyst for the biphenyl conjugation results simultaneously in picolinamide-directed...

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Scheme 12: Pd(0)-mediated cyclisation of imidoyl-selenides forming 6-arylphenanthridine derivatives [16]. The inse...

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Scheme 13: Palladium-catalysed phenanthridine synthesis.

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Scheme 14: Aerobic domino Suzuki coupling combined with Michael addition reaction in the presence of a Pd(OAc)₂...

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Scheme 15: Rhodium-catalysed alkyne [2 + 2 + 2] cycloaddition reactions [36].

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Scheme 16: The O-acetyloximes derived from 2′-arylacetophenones underwent N–O bond cleavage and intramolecular ...

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Scheme 17: C–H arylation with aryl chloride in the presence of a simple diol complex with KOt-Bu (top) [39]; for s...

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Scheme 18: The subsequent aza-Claisen rearrangement, ring-closing enyne metathesis and Diels–Alder reaction – ...

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Scheme 19: Phenanthridine central-ring cyclisation with simultaneous radical-driven phosphorylation [42].

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Scheme 20: Three component reaction yielding the benzo[a]phenanthridine core in excellent yields [44].

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Scheme 21: a) Reaction of malononitrile and 1,3-indandione with BEP to form the cyclised DPP products; b) pH c...

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Figure 1: Schematic presentation of the intercalative binding mode by the neighbour exclusion principle and i...

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Figure 2: Urea and guanidine derivatives of EB with modified DNA interactions [57].

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Figure 3: Structure of mono- (3) and bis-biguanide (4) derivative. Fluorescence (y-axis normalised to startin...

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Scheme 22: Bis-phenanthridinium derivatives (5–7; inert aliphatic linkers, R = –(CH₂)₄– or –(CH₂)₆–): rigidity...

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Figure 4: Series of amino acid–phenanthridine building blocks (general structure 10; R = H; Gly) and peptide-...

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Figure 5: General structure of 45 bis-ethidium bromide analogues. Reproduced with permission from [69]. Copyright...

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Scheme 23: Top: Recognition of poly(U) by 12 and ds-polyAH⁺ by 13; bottom: Recognition of poly(dA)–poly(dT) by ...

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Figure 6: The bis-phenanthridinium–adenine derivative 15 (LEFT) showed selectivity towards complementary UMP;...

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Figure 7: The neomycin–methidium conjugate targeting DNA:RNA hybrid structures [80].

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Figure 8: Two-colour RNA intercalating probe for cell imaging applications: Left: Chemical structure of EB-fl...

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Figure 9: The ethidium bromide nucleosides 17 (top) and 18 (bottom). DNA duplex set 1 and 2 (E = phenanthridi...

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Figure 10: Left: various DNA duplexes; DNA1 and DNA2 used to study the impact on the adjacent basepair type on...

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Figure 11: Structure of 4,9-DAP derivative 19; Rright: MIAPaCa-2 cells stained with 10 μM 19 after 60 and 120 ...

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Figure 12: Examples of naturally occurring phenanthridine analogues.

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Published 10 Dec 2014

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Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives

Marijana Radić Stojković,
Marko Škugor,
Łukasz Dudek,
Jarosław Grolik,
Julita Eilmes and
Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2175–2185, doi:10.3762/bjoc.10.225

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Scheme 1: Studied DBTAA–adenine conjugates (AP3, AP3am, AP5, AP6) [11], and the reference compounds lacking adeni...

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Scheme 2: Preparations of the products AP3am and AP5. Starting compounds were synthesized according to previo...

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Figure 1: Changes in the UV–vis spectrum of AP3am (c = 1.0 × 10⁻⁵ mol dm⁻³) upon titration with poly dA–poly ...

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Figure 2: Induced CD bands observed for AP3, AP3am, AP6 for poly dA–poly dT and poly (dAdT)₂ (c = 3.0 × 10⁻⁵ ...

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Figure 3: Comparison of AP3 ICD bands for ss-DNA (dA and dT) with alternating- and homo-AT ds-polynucleotides...

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Figure 4: Self-folding of AP5 (upper left – note the stacking of DBTAA and adenine) and AP3 (lower left – not...

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Figure 5: Schematic presentation of self-folded AP5 (free AP5 see Figure 4; upper left) in the minor groove of poly d...

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Published 12 Sep 2014

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