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6 article(s) from Piantanida, Ivo

A tribute to Carsten Schmuck

Jochen Niemeyer,
Ivo Piantanida and
Thomas Schrader

Beilstein J. Org. Chem. 2021, 17, 2795–2798, doi:10.3762/bjoc.17.190

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Figure 1: Carsten Schmuck.

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Editorial

Published 29 Nov 2021

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Naphthalene diimide bis-guanidinio-carbonyl-pyrrole as a pH-switchable threading DNA intercalator

Poulami Jana,
Filip Šupljika,
Carsten Schmuck and
Ivo Piantanida

Beilstein J. Org. Chem. 2020, 16, 2201–2211, doi:10.3762/bjoc.16.185

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Graphical Abstract

Scheme 1: DNA-targeting roles of the structural components incorporated in the design of the novel small mole...

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Scheme 2: Synthesis of compound 4. Conditions: a) mono-N-Boc-ethylenediamine, DMF, 90 °C; b) i) trifluoroacet...

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Figure 1: UV–vis titrations of compound 4 (c = 1.0 × 10⁻⁶ M), with ct-DNA at pH 7.0 (a) and at pH 5 (b). Inse...

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Figure 2: a) CD titration of ct-DNA (c = 3.0 × 10⁻⁵ M) with compound 4 at pH 7.0 (Na cacodylate buffer, I = 0...

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Figure 3: CD titration of poly(rA)–poly(rU) (c = 3.0 × 10⁻⁵ M) with compound 4 at a) pH 7.0 (Na cacodylate bu...

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Figure 4: CD titration of ds-DNAs (c = 3.0 × 10⁻⁵ M) with 4 for ratio r_[₄_{]/ [DNA]} = 0.4. Done at pH 5.0 (Na c...

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Figure 5: ITC experiments of poly(dAdT)–poly(dAdT) (c = 5.0 × 10⁻⁵ M) titrated with compound 4. Dots represen...

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Figure 6: AFM image of a) ct-DNA showing a fibre-like structure with a length of several micrometres; b) upon...

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Published 08 Sep 2020

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Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA

Annike Weißenstein,
Myroslav O. Vysotsky,
Ivo Piantanida and
Frank Würthner

Beilstein J. Org. Chem. 2020, 16, 2032–2045, doi:10.3762/bjoc.16.170

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Figure 1: Structures of investigated compounds stressing steric differences in linker length attached to the ...

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Scheme 1: Synthesis of water-soluble naphthalene diimides 3a,b, and 5.

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Figure 2: UV–vis absorption (solid line) and fluorescence spectra (dashed line) of NDI 3a,b, and 5 (c = 4.5 ×...

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Figure 3: Calculations for Cl-NDI-NMe model compound (at the B3LYP/6-31+G** level of theory) in water (PCM). ...

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Figure 4: (a) Melting curve of poly(dA-dT)₂ alone and after the addition of NDI 3a,b, and 5 (r = 0.3 ([NDI]/[...

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Figure 5: Changes in fluorescence intensity (spectra are normalized) of (a) 3a (c = 1.0 × 10⁻⁶ M), (b) 3b (c ...

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Figure 6: Calorimetric titration of a poly(dG-dC)₂ solution in sodium cacodylate buffer (pH 5.0) at 298 K wit...

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Figure 7: CD titration of poly(dG-dC)₂ (c = 2.0 × 10⁻⁵ M) with (a) 3a, (b) 3b, and (c) 5 with increasing mola...

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Figure 8: Schematic representation of the alignment of the intercalating 3a (left) and 3b (right) between the...

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Published 19 Aug 2020

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Polarization spectroscopy methods in the determination of interactions of small molecules with nucleic acids – tutorial

Tamara Šmidlehner,
Ivo Piantanida and
Gennaro Pescitelli

Beilstein J. Org. Chem. 2018, 14, 84–105, doi:10.3762/bjoc.14.5

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Figure 1: Plane polarized light (PP, cyan) as the sum of the left and right circularly polarized light (L-CP,...

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Figure 2: Schematic representation of ligand binding modes to DNA or RNA (left to right: DNA minor groove bin...

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Scheme 1: Principal electronic transitions of nucleobases (uracil is similar to thymine, Thy). The arrows dep...

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Figure 3: Exciton coupling mechanism in its degenerate (top) and non-degenerate version (bottom). a) Chiralit...

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Figure 4: ECD and UV (inset) spectra of poly(dG-dC)–poly(dG-dC) in the B and Z-form, obtained in 59% and 67% ...

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Figure 5: Schematic illustration of an ECD instrument. Legend: S, source; M, monochromator (wavelength select...

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Figure 6: Exciton coupling in the G-quadruplex [d(TG₄T)]₄. For this sequence, the quadruplex is formed by fou...

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Figure 7: Empirical analysis of ECD and flow LD spectra to establish the preferred orientation of a ligand bo...

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Figure 8: CD titration of poly rA-poly rU (left) and poly rU (right) (c(polynucleotide) = 2.0 × 10⁻⁵ mol dm⁻³...

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Figure 9: a) Schematic diagram of a flow LD instrument. b) Definition of the optical factor relating the dire...

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Figure 10: LD spectrum of calf thymus (ct) DNA (c = 2 × 10⁻⁴ M), pH 7, sodium cacodylate buffer, I = 0.05 M.

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Figure 11: Schematic illustration of an FDCD a) and a CPL b) instrument. Legend: S, source; M, monochromator (...

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Figure 12: Minimal model to be considered to simulate the ICD spectrum of an intercalated ligand. ICD will be ...

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Figure 13: Schematic representation of the main steps for calculating the ICD spectrum of a ligand bound to a ...

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Review

Published 08 Jan 2018

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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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Review

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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