Supporting Information
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- Δευκαλίων Ζυγομαλάς
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1 Supporting Information for Pyrene nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies Artur Jabłoński 1, Yannic Fritz 2, Hans-Achim Wagenknecht 2, Rafał Czerwieniec 3, Tytus Bernaś 4, Damian Trzybiński 5, Krzysztof Woźniak 5 and Konrad Kowalski *1 Address: 1 Faculty of Chemistry, Department of Organic Chemistry, University of Łódź, Tamka 12, PL Łódź, Poland, 2 Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz- Haber-Weg 6, Karlsruhe, Germany, 3 Universität Regensburg, Institut für Physikalische und Theoretische Chemie, Universitätsstraße 31, D Regensburg, Germany, 4 Nencki Institute of Experimental Biology, Polish Academy of Sciences, ul. Pasteura 3, Warsaw, Poland and 5 Faculty of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki and Wigury 101, Warszawa, Poland * Corresponding author Konrad Kowalski - kondor15@wp.pl 1 H NMR spectra, refinement data, spectra in HeLa cells S1
2 Contents Figure S1 1 H NMR of compound 1 Figure S2 1 H NMR of compound 2 Figure S3 1 H NMR of compound 3 Figure S4 1 H NMR of compound 4 Figure S5 1 H NMR of compound 5 Table S1 Crystal and structure refinement data for compound 2 Table S2 Bond lengths, valence and torsion angles in 2 Table S3 The geometry of hydrogen bonds in 2 Table S4 The geometry of halogen bond in 2 Figure S6 The arrangement of molecules in the crystal of 2 Figure S7 Fluorescence emission spectra of 4 and 5 in HeLa cells S3 S4 S5 S6 S7 S8 S9 S12 S13 S14,S15 S16 S2
3 Figure S1: 1 H NMR of compound 1. S3
4 Figure S2: 1 H NMR of compound 2. S4
5 Figure S3: 1 H NMR of compound 3. S5
6 Figure S4: 1 H NMR of compound 4. S6
7 Figure S5: 1 H NMR of compound 5. S7
8 Table S1: Crystallographic data and structural refinement details of 2. Compound 2 Empirical formula C 24H 18N 2O 3, CHCl 3 Formula weight Temperature/K 100(2) Crystal system Monoclinic Space group I2/a a/å (2) b/å (5) c/å (3) β/ (9) Volume/Å (7) Z 8 ρ calc/g/cm μ/mm F(000) 2064 Crystal size/mm Radiation CuKα (λ = Å) 2Θ range for data collection/ 2.24 to Index ranges -26 h 24, -6 k 6, -49 l 49 Reflections collected Independent reflections 4482 [R int = 0.069] Data/restraints/parameters 4482/0/302 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = Largest diff. peak/hole / e Å /-0.64 S8
9 Table S2: Bond lengths, valence and torsion angles in in the chloroform solvate of 2 (Å, ). C1 C (2) C15 C (2) C1 C (2) C17 C (2) C1 C (2) C17 O (2) C2 C (2) C2 C (2) C3 C (2) C4 C (3) C19 N (2) C5 C (2) C21 N (2) C5 C (2) C21 N (2) C21 O (2) C6 C (3) C23 C (3) C23 N (2) C7 C (3) C23 O (2) C24 C (3) C8 C (2) C24 C (3) C9 C (3) C9 C (2) C25 N (2) C10 C (3) C11 C (2) N22 H (2) C12 C (2) C12 C (2) C30 Cl (2) C30 Cl (2) C13 C (2) C30 Cl (2) C2 C1 C (15) C9 C16 C (16) C14 C1 C (15) C1 C17 C (14) C14 C1 C (15) O26 C17 C (15) C1 C2 C (16) O26 C17 C (15) C15 C2 C (15) C15 C2 C (15) C4 C3 C (16) C19 C18 C (14) C3 C4 C (17) C6 C5 C (17) C6 C5 C (16) N20 C19 C (13) C16 C5 C (16) C7 C6 C (17) N20 C21 N (14) O27 C21 N (15) O27 C21 N (15) N22 C23 C (15) O28 C23 C (16) S9
10 O28 C23 N (16) C7 C8 C (17) C23 C24 C (17) C25 C24 C (16) C8 C9 C (17) C25 C24 C (18) C8 C9 C (17) C16 C9 C (16) C24 C25 N (17) C11 C10 C (17) C10 C11 C (17) C13 C12 C (16) C13 C12 C (16) C21 N20 C (14) C15 C12 C (16) C21 N20 C (14) C25 N20 C (14) C14 C13 C (16) C21 N22 C (15) C13 C14 C (16) Cl31 C30 Cl (12) C2 C15 C (15) Cl31 C30 Cl (11) C12 C15 C (15) C12 C15 C (15) Cl32 C30 Cl (11) C5 C16 C (16) C5 C16 C (15) C1 C2 C3 C (18) C12 C15 C16 C (16) C1 C2 C15 C12 2.4(2) C12 C15 C16 C9 0.2(2) C1 C2 C15 C (15) C13 C12 C15 C2 2.3(2) C1 C17 C18 C (14) C13 C12 C15 C (15) C2 C1 C14 C13 2.6(3) C14 C1 C2 C (17) C2 C1 C17 C (15) C14 C1 C2 C15 0.0(2) C2 C1 C17 O (3) C14 C1 C17 C (2) C2 C3 C4 C5 0.2(3) C14 C1 C17 O (16) C2 C15 C16 C5 0.1(2) C15 C2 C3 C4 1.1(3) C2 C15 C16 C (15) C15 C12 C13 C14 0.3(3) C3 C2 C15 C (16) C16 C5 C6 C7 1.3(3) C3 C2 C15 C16 0.9(2) C16 C9 C10 C11 0.8(3) C3 C4 C5 C (19) C17 C1 C2 C3 2.2(3) C3 C4 C5 C16 0.9(3) C17 C1 C2 C (15) C4 C5 C6 C (18) C17 C1 C14 C (15) C4 C5 C16 C (16) C17 C18 C19 N (13) S10
11 C4 C5 C16 C15 1.0(3) C18 C19 N20 C (18) C5 C6 C7 C8 0.4(3) C18 C19 N20 C (19) C6 C5 C16 C9 1.0(3) C23 C24 C25 N20 0.2(3) C6 C5 C16 C (16) C24 C23 N22 C21 1.0(3) C6 C7 C8 C9 0.8(3) C24 C25 N20 C (19) C7 C8 C9 C (18) C24 C25 N20 C21 2.2(3) C7 C8 C9 C16 1.1(3) C29 C24 C25 N (2) C8 C9 C10 C (18) N20 C21 N22 C23 1.3(3) C8 C9 C16 C5 0.2(3) N22 C21 N20 C (14) C8 C9 C16 C (16) N22 C21 N20 C25 2.9(2) C9 C10 C11 C12 0.9(3) N22 C23 C24 C25 1.7(3) C10 C9 C16 C (16) N22 C23 C24 C (2) C10 C9 C16 C15 1.2(3) O26 C17 C18 C19 1.6(2) C10 C11 C12 C (17) O27 C21 N20 C19 0.8(3) C10 C11 C12 C15 2.4(3) O27 C21 N20 C (17) C11 C12 C13 C (16) O27 C21 N22 C (17) C11 C12 C15 C (16) O28 C23 C24 C (19) C11 C12 C15 C16 2.0(2) O28 C23 C24 C29 1.8(3) C12 C13 C14 C1 2.8(3) O28 C23 N22 C (16) S11
12 Table S3: The geometry of hydrogen bonds in 2. D H A d(d A) (Å) < D H A ( ) N22 H22 O27 i 2.882(2) 174(3) C3 H3 O26* 2.879(2) 126 C14 H14 O27 ii 3.324(2) 162 C18 H18A O28 iii 3.309(2) 161 C18 H18B O27 ii 3.251(2) 143 C25 H25 O26 iv 3.442(2) 170 Symmetry codes: (i) x + 1/2, y + 7/2, z + 3/2; (ii) x, y 1/2, z; (iii) x + 1/2, y + 5/2, z + 3/2; (iv) x + 1, y 1/2, z + 3/2; (*) intramolecular interaction. S12
13 Table S4: The geometry of halogen bond in 2. D X A d(x A) (Å) d(d A) (Å) < D X A ( ) C30 Cl31 O (2) 4.644(2) 157.9(2) S13
14 In the crystal, inversely oriented molecules of 2 are linked by N H O hydrogen bonds, through R 2 2(8) synthon, into pair (N22 H22 O27, d(d A) = 2.882(2) Å, < D H A = 174(3) ) (Fig. S6a). Each molecule of 2 in such formed dimer is further incorporated in the Cl O halogen bond with neighboring molecule of chloroform (C30 Cl31 O28, d(x A) = 2.972(2) Å, < D X A = 157.9(3) )(Fig. 6a). Adjacent dimers are thus participating in the network of weak C H O hydrogen bonds which is leading to formation of infinite 2D supramolecular framework, running along (001) plane (Fig. 6b). Detailed analysis performed by PLATON program (A. L. Spek, Acta Crystallogr. Sect. D 2009, 65, ) indicates presence of the π-π and C=O π contacts between neighboring molecules of 2 within aforementioned supramolecular framework. The adjacent 2D-frameworks are oriented anti-parallel to themselves (Fig. 6c ) and there is no direct interaction between them. S14
15 Figure S6: The arrangement of molecules in the crystal of the chloroform solvate of 2, where: (a) dimer of molecules of 2 incorporated in the Cl O halogen bonds with neighboring solvent molecules; (b) view from the side on 2D supramolecular framework formed by the adjacent molecules incorporated in halogen and hydrogen bonds; (c) general view on the structure (single 2D-framework is highlighted by green rectangle) along b-direction. The N H O, C H O and Cl O intermolecular interactions are showed as a dashed lines. The H- atoms not participating in intermolecular interactions were omitted for clarity. Symmetry code: (i) x + 1/2, y + 7/2, z + 3/2. S15
16 Figure S7: Fluorescence spectra 4 (blue line) and 5 (green line) measured in cytoplasm of live HeLa cells. S16
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