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Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supplementary information Hybrids of acylated homoserine lactone and nitric oxide donors as inhibitors of quorum sensing and virulence factors in Pseudomonas aeruginosa Samuel K. Kutty a, Nicolas Barraud b, Kitty K. K. Ho a, George M. Iskander a, Renate Griffith c, Scott A. Rice d,e, Mark Willcox f, David StC Black a and Naresh Kumar a * Supporting Information 1) 1 H and 13 C NMR spectra of synthesised compounds tested for activity 2) X-ray crystal structure information for 7a and 22a

1) 1 H and 13 C NMR spectra of synthesised compounds 1 H NMR spectrum of Compound 7a in CDCl 3 N 2 13 C NMR spectrum of Compound 7a in CDCl 3

1 H NMR spectrum of Compound 7b in CDCl 3 N 2 13 C NMR spectrum of Compound 7b in CDCl 3

1 H NMR spectrum of Compound 7c in CDCl 3 N 2 13 C NMR spectrum of Compound 7c in CDCl 3

1 H NMR spectrum of Compound 7d in CDCl 3 N 2 13 C NMR spectrum of Compound 7d in CDCl 3

1 H NMR spectrum of Compound 7e in CDCl 3 N 2 13 C NMR spectrum of Compound 7e in CDCl 3

1 H NMR spectrum of Compound 10a in CDCl 3 N 2 13 C NMR spectrum of Compound 10a in CDCl 3

1 H NMR spectrum of Compound 10b in CDCl 3 N 2 13 C NMR spectrum of Compound 10b in CDCl 3

1 H NMR spectrum of Compound 13 in DMS-d6 H N N 2 13 C NMR spectrum of Compound 13 in DMS-d6

1 H NMR spectrum of Compound 21a in CDCl 3 N N N N Me 13 C NMR spectrum of Compound 21a in CDCl 3

1 H NMR spectrum of Compound 21b in CDCl 3 N N N N Me 13 C NMR spectrum of Compound 21b in CDCl 3

1 H NMR spectrum of Compound 22a in CDCl 3 N 2 N N N N N 2 2) X-ray crystal structure information Structure determination Reflexion data were measured with an Enraf-Nonius CAD-4 diffractometer in θ/2θ scan mode using nickel filtered copper radiation (γ 1.5418Å). Reflexions with I>3σ(I) were considered observed. The structures were determined by direct phasing and Fourier methods. Hydrogen atoms were included in calculated position s and were assigned thermal parameters equal to those of the atom to which they were bonded. Positional and anisitropic thermal parameters for the nonhydrogen atoms were refined using full matrix least squares. Reflexion weights used were 1/σ2(Fo), with σ(fo) being derived from σ(io) = [σ2(io) + (0.04Io)2]1/2. The weighted residual is defined as Rw = (ΣwΔ2/ΣwFo2)1/2. Atomic scattering factors and anomalous dispersion parameters were from International Tables for X-ray crystallography1. Structure solutions were performed by SIR922 and refinements used RAELS3. RTEP-II4 running on a Macintosh was used for the structural diagrams.

Compound: 2-xo-2-(2-oxotetrahydrofuran-3-ylamino)ethyl nitrate (7a) Figure 1: RTEP diagram for 7a CCDC number: 1408469 Table 1. Experimental details Crystal data inp21byn Chemical formula C 6 H 8 N 2 6 M r 204.14 Crystal system, space group Temperature (K) 152 Monoclinic, P2 1 /n a, b, c (Å) 10.0324 (6), 5.2469 (2), 16.1420 (9) b ( ) 101.826 (3) V (Å 3 ) 831.66 (8) Z 4 Radiation type Mo Ka m (mm -1 ) 0.15 Crystal size (mm) 0.47 0.27 0.08 Data collection Diffractometer Absorption correction Bruker kappa APEXII CCD Diffractometer Multi-scan SADABS (Bruker, 2001) T min, T max 0.934, 0.988 No. of measured, independent and observed [I > 2s(I)] reflections R int 0.032 Refinement 6746, 1812, 1552 R[F 2 > 2s(F 2 )], wr(f 2 ), S 0.032, 0.089, 1.04 No. of reflections 1812

No. of parameters 127 No. of restraints 0 H-atom treatment H-atom parameters constrained Dρ max, Dρ min (e Å -3 ) 0.27, -0.24 Computer programs: APEX2 (Bruker, 2007), SHELXS-97 (Sheldrick, 2008), SHELXL-97 (Sheldrick, 2008), SHELXTL- Plus (Sheldrick, 2008). Table 2. Selected geometric parameters (Å, º) 1 C2 1.3362 (15) C2 C3 1.5171 (17) 1 C5 1.4634 (17) C3 C4 1.5223 (17) 2 C2 1.2065 (16) C3 H3 1.0000 3 C6 1.2210 (15) C4 C5 1.5226 (19) 4 N2 1.4037 (15) C4 H4B 0.9900 4 C7 1.4400 (15) C4 H4A 0.9900 5 N2 1.2017 (16) C5 H5B 0.9900 6 N2 1.2005 (15) C5 H5A 0.9900 N1 C6 1.3363 (16) C6 C7 1.5244 (17) N1 C3 1.4388 (15) C7 H7B 0.9900 N1 H1 0.8800 C7 H7A 0.9900 C2 1 C5 109.89 (10) C5 C4 H4B 111.5 N2 4 C7 112.50 (9) C3 C4 H4A 111.5 C6 N1 C3 121.31 (10) C5 C4 H4A 111.5 C6 N1 H1 119.3 H4B C4 H4A 109.3 C3 N1 H1 119.3 1 C5 C4 105.00 (10) 6 N2 5 129.31 (13) 1 C5 H5B 110.7 6 N2 4 112.44 (11) C4 C5 H5B 110.7 5 N2 4 118.25 (11) 1 C5 H5A 110.7 2 C2 1 122.41 (12) C4 C5 H5A 110.7 2 C2 C3 127.51 (11) H5B C5 H5A 108.8 1 C2 C3 110.08 (10) 3 C6 N1 124.92 (11) N1 C3 C2 112.01 (10) 3 C6 C7 121.16 (11) N1 C3 C4 116.74 (10) N1 C6 C7 113.91 (10) C2 C3 C4 102.41 (10) 4 C7 C6 109.72 (10) N1 C3 H3 108.4 4 C7 H7B 109.7

C2 C3 H3 108.4 C6 C7 H7B 109.7 C4 C3 H3 108.4 4 C7 H7A 109.7 C3 C4 C5 101.36 (10) C6 C7 H7A 109.7 C3 C4 H4B 111.5 H7B C7 H7A 108.2 C7 4 N2 6 170.32 (11) N1 C3 C4 C5-153.99 (11) C7 4 N2 5-10.48 (16) C2 C3 C4 C5-31.27 (12) C5 1 C2 2 179.63 (11) C2 1 C5 C4-19.87 (14) C5 1 C2 C3-1.07 (13) C3 C4 C5 1 31.65 (13) C6 N1 C3 C2 98.81 (13) C3 N1 C6 3 2.77 (19) C6 N1 C3 C4-143.60 (12) C3 N1 C6 C7-177.92 (10) 2 C2 C3 N1-33.54 (17) N2 4 C7 C6-65.25 (13) 1 C2 C3 N1 147.21 (10) 3 C6 C7 4-11.01 (16) 2 C2 C3 C4-159.40 (12) N1 C6 C7 4 169.65 (10) 1 C2 C3 C4 21.34 (13) Compound: 2 -(2,4-Dinitrophenyl)-1-(4-(4-oxo-4-(2-oxotetrahydrofuran-3-ylamino)butanoyl)piperazin-1-yl)diazen-1-ium- 1,2-diolate (22a). Figure 2: RTEP diagram for 22a. CCDC number 1408468 Table 3. Experimental details sam12_p21byc Crystal data

Chemical formula C 18 H 17 N 7 10 CHCl 3 M r 610.75 Crystal system, space group Monoclinic, P2 1 /c Temperature (K) 156 a, b, c (Å) 12.6131 (5), 26.049 (1), 8.1912 (4) β ( ) 108.884 (2) V (Å 3 ) 2546.43 (19) Z 4 Radiation type Mo Kα µ (mm -1 ) 0.43 Crystal size (mm) 0.30 0.10 0.05 Data collection Diffractometer Absorption correction CCD area detector diffractometer Multi-scan SADABS2007/4 (Bruker,2007/4) was used for absorption correction. wr2(int) was 0.0516 before and 0.0439 after correction. The Ratio of minimum to maximum transmission is 0.8938. The λ/2 correction factor is 0.0015. T min, T max 0.667, 0.746 No. of measured, independent and observed [I > 2σ(I)] reflections 17884, 4460, 3699

R int 0.038 (sin / ) max (Å -1 ) 0.595 Refinement R[F 2 > 2σ(F 2 )], wr(f 2 ), S 0.270, 0.675, 3.51 No. of reflections 4460 No. of parameters 380 No. of restraints 12 H-atom treatment H-atom parameters constrained max, min (e Å -3 ) 1.44, -1.25 Computer programs: SAINT v7.46a (Bruker, 2008), SHELXL (Sheldrick, 2008), lex2 (Dolomanov et al., 2009). Table 4: Geometric parameters (Å, º) C1 C2 1.431 (19) C15 C19' 1.50 (3) C1 H1 0.9500 C15' C16' 1.58 (4) C1CL H1CL 1.0000 C16' C17' 1.46 (5) C2 N1 1.464 (19) C16' H2XA 0.9900 C3 C2 1.34 (2) C16' H2XB 0.9900 C3 C4 1.44 (2) C17 C16 1.60 (5) C3 H3 0.9500 C17 H3XA 0.9900 C4 C5 1.33 (2) C17 H3XB 0.9900 C4 N2 1.506 (17) C17' H1AA 0.9900 C5 5 1.414 (17) C17' H1AB 0.9900 C6 C1 1.404 (19) C19 C15' 1.56 (3) C6 C5 1.40 (2) C19 9 1.211 (17) C6 H6 0.9500 C19 10' 1.35 (3) C7 C8 1.50 (2) Cl1 C1CL 1.725 (18) C7 H7A 0.9900 Cl2 C1CL 1.741 (19) C7 H7B 0.9900 Cl3 C1CL 1.78 (2) C8 H9A 0.9900 N1 1 1.252 (18) C8 H9B 0.9900 N1 2 1.242 (19) C8 N6 1.496 (19) N2 3 1.183 (17) C9 C10 1.53 (2) N2 4 1.205 (16) C9 H2 0.9900 N3 N4 1.276 (17) C9 H4 0.9900 N4 N5 1.466 (17) C9 N6 1.431 (18) N4 6 1.225 (16) C10 H10A 0.9900 N5 C7 1.44 (2)

C10 H10B 0.9900 N5 C10 1.479 (18) C11 C12 1.47 (3) N6 C11 1.37 (2) C11 7 1.17 (2) N7 C15 1.57 (4) C12 H12 0.9500 N7 C15' 1.39 (3) C13 C12 1.44 (3) 5 N3 1.409 (16) C13 H13 0.9500 6 H6A 0.8400 C14 C13 1.46 (2) 9 C19' 1.211 (17) C14 N7 1.36 (3) 10 C17 1.64 (5) C14 8 1.21 (2) 10 C19' 1.55 (2) C15 C16 1.27 (3) 10' C17' 1.59 (4) Cl1 C1CL Cl2 116.5 (12) N6 C9 H2 109.6 Cl1 C1CL Cl3 108.5 (11) N6 C9 H4 109.6 Cl1 C1CL H1CL 108.1 N6 C9 C10 110.4 (12) Cl2 C1CL Cl3 107.2 (11) H2 C9 H4 108.1 Cl2 C1CL H1CL 108.1 C10 C9 H2 109.6 Cl3 C1CL H1CL 108.1 C10 C9 H4 109.6 N3 5 C5 109.8 (10) N5 C10 C9 107.6 (11) N4 6 H6A 109.5 N5 C10 H10A 110.2 C19' 10 C17 108.5 (19) N5 C10 H10B 110.2 1 N1 C2 121.1 (13) C9 C10 H10A 110.2 2 N1 1 123.9 (14) C9 C10 H10B 110.2 2 N1 C2 114.7 (14) H10A C10 H10B 108.5 3 N2 4 122.5 (12) 7 C11 N6 118.7 (17) 3 N2 C4 119.6 (13) 7 C11 C12 128.0 (18) 4 N2 C4 117.8 (12) N6 C11 C12 112.8 (16) N4 N3 5 103.0 (11) C11 C12 H12 122.5 6 N4 N3 130.6 (13) C13 C12 C11 115.0 (16) 6 N4 N5 115.6 (12) C13 C12 H12 122.5 N3 N4 N5 113.8 (12) C12 C13 H13 122.2 N4 N5 C10 111.5 (12) C12 C13 C14 115.5 (17) C7 N5 N4 111.7 (11) C14 C13 H13 122.2 C7 N5 C10 112.6 (12) 8 C14 N7 120.7 (16) C9 N6 C8 114.7 (13) 8 C14 C13 127 (2) C11 N6 C8 124.9 (13) N7 C14 C13 112.3 (16) C11 N6 C9 120.3 (13) N7 C15' C19 114 (2) C14 N7 C15' 136 (2) N7 C15' C16' 113 (2) C14 N7 C15 108 (2) C19 C15' C16' 100 (2) C2 C1 H1 120.9 9 C19 C15' 125.7 (18) C6 C1 H1 120.9 9 C19 10' 116.8 (15) C6 C1 C2 118.2 (12) 10' C19 C15' 117.4 (19) C1 C2 N1 117.6 (13) 9 C19' 10 122.8 (13) C3 C2 N1 118.9 (13) 9 C19' C15 136.4 (15) C3 C2 C1 123.6 (12) C15 C19' 10 100.8 (15) C2 C3 H3 122.0 C19 10' C17' 97 (2) C2 C3 C4 115.9 (12) C19' C15 N7 108.0 (19) C4 C3 H3 122.0 C16 C15 N7 122 (3) C3 C4 N2 112.5 (12) C16 C15 C19' 120 (2) C5 C4 N2 124.8 (13) 10' C17' H1AA 109.8 C5 C4 C3 122.6 (12) 10' C17' H1AB 109.8 C4 C5 5 118.5 (13) H1AA C17' H1AB 108.3

C4 C5 C6 121.1 (12) C16' C17' 10' 109 (3) C6 C5 5 120.2 (13) C16' C17' H1AA 109.8 C1 C6 H6 120.8 C16' C17' H1AB 109.9 C5 C6 C1 118.3 (12) C15' C16' H2XA 111.8 C5 C6 H6 120.8 C15' C16' H2XB 111.9 N5 C7 H7A 110.1 C17' C16' C15' 100 (2) N5 C7 H7B 110.1 C17' C16' H2XA 111.8 N5 C7 C8 108.1 (14) C17' C16' H2XB 111.9 H7A C7 H7B 108.4 H2XA C16' H2XB 109.6 C8 C7 H7A 110.1 10 C17 H3XA 112.0 C8 C7 H7B 110.1 10 C17 H3XB 112.0 N6 C8 C7 107.4 (11) H3XA C17 H3XB 109.6 N6 C8 H9A 110.2 C16 C17 10 99 (3) N6 C8 H9B 110.2 C16 C17 H3XA 112.0 C7 C8 H9A 110.2 C16 C17 H3XB 112.0 C7 C8 H9B 110.2 C15 C16 C17 111 (2) H9A C8 H9B 108.5 5 N3 N4 6 4.0 (19) C4 C3 C2 C1 3.5 (19) 5 N3 N4 N5 175.4 (10) C4 C5 5 N3 179.5 (11) 6 N4 N5 C7 41.6 (16) C5 5 N3 N4 179.7 (10) 6 N4 N5 C10 168.6 (12) C5 C4 N2 3 164.6 (15) 7 C11 C12 C13 13 (3) C5 C4 N2 4 19 (2) 8 C14 N7 C15' 10 (4) C5 C6 C1 C2 2.4 (17) 8 C14 N7 C15 7 (2) C6 C1 C2 N1 179.1 (11) 8 C14 C13 C12 26 (3) C6 C1 C2 C3 1.9 (18) 9 C19 C15' N7 46 (3) C6 C5 5 N3 4.9 (17) 9 C19 C15' C16' 167.7 (17) C7 N5 C10 C9 60.4 (15) 9 C19 10' C17' 169 (3) C7 C8 N6 C9 57.2 (19) 10 C17 C16 C15 7 (4) C7 C8 N6 C11 127.2 (17) N2 C4 C5 5 3.7 (19) C8 N6 C11 7 177.4 (15) N2 C4 C5 C6 179.3 (11) C8 N6 C11 C12 5 (2) N3 N4 N5 C7 138.9 (13) C9 N6 C11 7 2 (2) N3 N4 N5 C10 11.9 (16) C9 N6 C11 C12 170.6 (16) N4 N5 C7 C8 168.7 (13) C10 N5 C7 C8 64.9 (17) N4 N5 C10 C9 173.1 (10) C10 C9 N6 C8 54.7 (16) N5 C7 C8 N6 59.1 (19) C10 C9 N6 C11 129.5 (15) N6 C9 C10 N5 53.0 (15) C13 C14 N7 C15' 174 (3) N6 C11 C12 C13 158.4 (19) C13 C14 N7 C15 168.2 (18) N7 C14 C13 C12 159 (2) C14 N7 C15' C19 33 (4) N7 C15' C16' C17' 151 (3) C14 N7 C15' C16' 80 (3) N7 C15 C19' 9 28 (4) C14 N7 C15 C19' 90 (2) N7 C15 C19' 10 151 (2) C14 N7 C15 C16 125 (3) N7 C15 C16 C17 139 (3) C14 C13 C12 C11 167 (2) C1 C2 N1 1 6.9 (18) C15' C19 10' C17' 15 (4) C1 C2 N1 2 178.5 (13) C15' C16' C17' 10' 42 (5) C1 C6 C5 5 179.6 (11) C19 C15' C16' C17' 29 (3) C1 C6 C5 C4 4.9 (19) C19 10' C17' C16' 36 (5) C2 C3 C4 N2 176.8 (11) C19' 10 C17 C16 10 (3) C2 C3 C4 C5 1.0 (19) C19' C15 C16 C17 1 (5) C3 C2 N1 1 172.3 (13) 10' C19 C15' N7 129 (3)

C3 C2 N1 2 2.4 (19) 10' C19 C15' C16' 8 (3) C3 C4 N2 3 17.7 (18) C17 10 C19' 9 170 (2) C3 C4 N2 4 158.4 (12) C17 10 C19' C15 10 (3) C3 C4 C5 5 178.8 (12) C16 C15 C19' 9 173 (3) C3 C4 C5 C6 3 (2) C16 C15 C19' 10 6 (4) C4 C3 C2 N1 177.4 (11)

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