Synthesis and Biological Evaluation of Novel Acyclic and Cyclic Glyoxamide derivatives as Bacterial Quorum Sensing and Biofilm Inhibitors

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Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Synthesis and Biological Evaluation of Novel Acyclic and Cyclic Glyoxamide derivatives as Bacterial Quorum Sensing and Biofilm Inhibitors Shashidhar Nizalapur a, Onder Kimyon b, Eugene Yee a, Mohan M. Bhadbhade c, Mike Manefield b, Mark Willcox d, David StC Black a and Naresh Kumar a * a School of Chemistry, UNSW Sydney, NSW 2052, Australia. UNSW Australia, Sydney, NSW 2052, Australia. *E mail: n.kumar@unsw.edu.au* Tel: +61 29385 4698; Fax: +61 29385 6141 b School of Biotechnology and Biomolecular Sciences, UNSW Australia, Sydney, NSW 2052, Australia. c Solid State & Elemental Analysis Unit, Mark Wainwright Analytical Centre, Division of Research, UNSW Australia, NSW 2052, Australia. d School of Optometry and Vision Science, UNSW Australia, Sydney, NSW 2052, Australia. Contents 1 HNMR and 13 CNMR of 1-(2-Chloroacetyl) indoline-2,3-dione (12)...4 1 HNMR and 13 CNMR of 5-Chloro-1-(2-chloroacetyl)indoline-2,3-dione (14)...5 1HNMR and 13CNMR of 1-(2-Chloroacetyl)-5-fluoroindoline-2,3-dione (15)...6 1HNMR and 13CNMR of 1-(2-Chloroacetyl)-5-methylindoline-2,3-dione (16)...7 1HNMR and 13CNMR of 1-(2-chloroacetyl)-5-nitroindoline-2,3-dione (17)...8 1 HNMR and 13 CNMR of 2-(2-(2-Chloroacetamido)phenyl)-2-oxo-N-(prop-2-yn-1-yl)acetamide (18)...9 1HNMR and 13CNMR of 2-(5-Bromo-2-(2-chloroacetamido)phenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide (18)...10 1HNMR and 13CNMR of 2-(5-Chloro-2-(2-chloroacetamido)phenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide (20)...11 1HNMR and 13CNMR OF 2-(2-(2-Chloroacetamido)-5-fluorophenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide (21)...12 1HNMR and 13CNMR OF 2-(2-(2-Chloroacetamido)-5-methylphenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide (22)...13 1HNMR and 13CNMR OF 2-(2-(2-Chloroacetamido)-5-nitrophenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide)(23)...14 1HNMR and 13CNMR OF 2-(2-(2-Azidoacetamido)phenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide (24)...15

1HNMR and 13CNMR OF 2-(2-(2-Azidoacetamido)-5-bromophenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide (25)...16 1HNMR and 13CNMR OF 2-(2-(2-Azidoacetamido)-5-chlorophenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide (26)...17 1HNMR and 13CNMR OF 2-(2-(2-Azidoacetamido)-5-fluorophenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide (27)...18 1HNMR and 13CNMR OF 2-(2-(2-Azidoacetamido)-5-methylphenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide (28)...19 1HNMR and 13CNMR of 2-(2-(2-azidoacetamido)-5-nitrophenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide (29)...20 1HNMR and 13CNMR of 14,15,29,30-Tetrahydro-5H,20H-dibenzo[h,s]bis([1,2,3]triazolo)[5,1- c:5',1'-n][1,4,7,12,15,18]hexaazacyclodocosine-6,12,13,21,27,28(7h,22h)-hexaone (30)...21 1HNMR and 13CNMR of 10,25-Difluoro-14,15,29,30-tetrahydro-5H,20H- dibenzo[h,s]bis([1,2,3]triazolo)[5,1-c:5',1'-n][1,4,7,12,15,18]hexaazacyclodocosine- 6,12,13,21,27,28(7H,22H)-hexaone (31)...22 1HNMR and 13CNMR of 10,25-Dimethyl-14,15,29,30-tetrahydro-5H,20H- dibenzo[h,s]bis([1,2,3]triazolo)[5,1-c:5',1'-n][1,4,7,12,15,18]hexaazacyclodocosine- 6,12,13,21,27,28(7H,22H)-hexaone (32)...23 Optical Density (OD) Measurements...24 The crystal data, data collection and refinements...25 Biofilm inhibition activity in P. aeruginosa...26 Biofilm inhibition activity in E. coli...26 Toxicity against human MRC-5 lung fibroblast cells...27

1 HNMR and 13 CNMR of 1-(2-Chloroacetyl) indoline-2,3-dione (12)

1 HNMR and 13 CNMR of 5-Chloro-1-(2-chloroacetyl)indoline-2,3-dione (14)

1HNMR and 13CNMR of 1-(2-Chloroacetyl)-5-fluoroindoline-2,3-dione (15)

1HNMR and 13CNMR of 1-(2-Chloroacetyl)-5-methylindoline-2,3-dione (16)

1HNMR and 13CNMR of 1-(2-chloroacetyl)-5-nitroindoline-2,3-dione (17)

1 HNMR and 13 CNMR of 2-(2-(2-Chloroacetamido)phenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide (18)

1HNMR and 13CNMR of 2-(5-Bromo-2-(2-chloroacetamido)phenyl)-2-oxo-N-(prop- 2-yn-1-yl)acetamide (18)

1HNMR and 13CNMR of 2-(5-Chloro-2-(2-chloroacetamido)phenyl)-2-oxo-N-(prop- 2-yn-1-yl)acetamide (20)

1HNMR and 13CNMR OF 2-(2-(2-Chloroacetamido)-5-fluorophenyl)-2-oxo-N-(prop- 2-yn-1-yl)acetamide (21)

1HNMR and 13CNMR OF 2-(2-(2-Chloroacetamido)-5-methylphenyl)-2-oxo-N-(prop- 2-yn-1-yl)acetamide (22)

1HNMR and 13CNMR OF 2-(2-(2-Chloroacetamido)-5-nitrophenyl)-2-oxo-N-(prop-2- yn-1-yl)acetamide)(23)

1HNMR and 13CNMR OF 2-(2-(2-Azidoacetamido)phenyl)-2-oxo-N-(prop-2-yn-1- yl)acetamide (24)

1HNMR and 13CNMR OF 2-(2-(2-Azidoacetamido)-5-bromophenyl)-2-oxo-N-(prop- 2-yn-1-yl)acetamide (25)

1HNMR and 13CNMR OF 2-(2-(2-Azidoacetamido)-5-chlorophenyl)-2-oxo-N-(prop-2- yn-1-yl)acetamide (26)

1HNMR and 13CNMR OF 2-(2-(2-Azidoacetamido)-5-fluorophenyl)-2-oxo-N-(prop-2- yn-1-yl)acetamide (27)

1HNMR and 13CNMR OF 2-(2-(2-Azidoacetamido)-5-methylphenyl)-2-oxo-N-(prop- 2-yn-1-yl)acetamide (28)

1HNMR and 13CNMR of 2-(2-(2-azidoacetamido)-5-nitrophenyl)-2-oxo-N-(prop-2- yn-1-yl)acetamide (29)

1HNMR and 13CNMR of 14,15,29,30-Tetrahydro-5H,20H- dibenzo[h,s]bis([1,2,3]triazolo)[5,1-c:5',1'-n][1,4,7,12,15,18]hexaazacyclodocosine- 6,12,13,21,27,28(7H,22H)-hexaone (30)

1HNMR and 13CNMR of 10,25-Difluoro-14,15,29,30-tetrahydro-5H,20H- dibenzo[h,s]bis([1,2,3]triazolo)[5,1-c:5',1'-n][1,4,7,12,15,18]hexaazacyclodocosine- 6,12,13,21,27,28(7H,22H)-hexaone (31)

1HNMR and 13CNMR of 10,25-Dimethyl-14,15,29,30-tetrahydro-5H,20H- dibenzo[h,s]bis([1,2,3]triazolo)[5,1-c:5',1'-n][1,4,7,12,15,18]hexaazacyclodocosine- 6,12,13,21,27,28(7H,22H)-hexaone (32)

Optical Density (OD) Measurements Table 3: Growth inhibition by the synthesized compounds against the PAMH602 and E. coli MT102 strains at three different concentrations. P. aeruginosa MH602 E. coli MT102 Concentrations (µm) Concentrations (µm) Compound 250 125 62.5 250 125 62.5 12 10.46±1.69 2.01±1.74 0.44±0.76 0.35±0.49 0.00 0.00 N-chloro-acetylisatins 13 7.91±0.75 1.02±3.34 0.00 15.30±9.02 0.00 0.00 14 2.75±2.13 0.00 0.42±0.72 24.34±2.55 2.12±2.99 5.50±4.86 15 4.56±6.41 1.97±3.41 2.19±3.80 0.00 0.00 0.00 16 1.63±1.55 0.00 0.00 31.14±2.39 12.38±0.75 6.83±5.96 17 1.53±1.85 0.00 0.00 25.50±4.19 0.00 0.00 Azido-alkyno- Cyclic-phenyl Alkynophenylglyoxamides phenylglyoxamides glyoxamides 18 6.24±0.20 0.00 0.00 25.08±4.24 4.55±2.26 0.00 19 5.26±1.80 4.31±4.39 2.17±3.77 0.00 0.00 0.00 20 7.59±0.44 1.77±7.16 0.00 0.00 0.00 0.00 21 9.09±0.85 0.00 5.50±6.69 8.13±1.87 5.54±1.33 6.89±11.93 22 3.98±0.38 0.00 0.00 16.55±8.81 17.71±2.75 13.33±6.45 23 1.05±1.48 0.00 0.76±1.32 0.00 0.00 0.00 24 4.74±4.45 0.00 0.00 6.54±4.85 4.40±3.70 5.59±8.15 25 4.40±6.22 2.87±4.97 4.31±4.29 0.00 0.00 0.00 26 8.31±2.81 2.09±3.62 4.16±6.27 10.49±9.84 15.37±1.70 0.93±0.81 27 4.60±6.50 0.00 3.40±4.48 17.65±3.08 3.07±3.42 0.00 28 5.40±3.74 0.00 0.00 4.80±19.7 1.49±7.08 2.18±9.12 29 7.31±2.77 0.35±7.82 0.00 15.94±3.08 6.01±4.61 3.22±12.41 30 17.04±6.01 0.00 0.00 9.62±6.54 0.00 0.00 31 4.24±2.65 3.71±6.29 2.38±2.21 0.00 0.00 0.00 32 5.46±7.72 0.37±9.53 0.55±0.78 0.00 0.00 0.00 Fu-30 88.11± 79.34± 1.79±12.5 98.8±11.7 99.7±0.3 75.6±0.5 Growth inhibition ± standard deviation of mean from at least two independent experiments. Compounds tested thrice in triplicate. 0 = No growth inhibition.

The crystal data, data collection and refinements Table 4. The data collection and refinements. Compound 30 complex with DMSO Crystal data Compound 30 complex with H 2 O Chemical formula C 2 H 6 OS 0.25(C 26 H 22 N 10 O 6 ) C 26 H 22 N 10 O 6 2(H 2 O) M r 220.76 606.57 Crystal system, space group Triclinic, P 1 Temperature (K) 154 158 Triclinic, P 1 a, b, c (Å) 9.7434 (5), 9.8225 (5), 12.0241 (6) 7.428 (4), 10.364 (7), 10.401 (6),, ( ) 92.357 (2), 104.697 (3), 106.384 (2) 60.81 (2), 86.52 (3), 88.14 (3) V (Å 3 ) 1060.01 (9) 697.8 (7) Z 4 1 Radiation type Mo K Mo K (mm -1 ) 0.29 0.11 Crystal size (mm) 0.10 0.06 0.06 0.11 0.09 0.05 Data collection Diffractometer Bruker APEX-II CCD Bruker APEX-II CCD Absorption correction Multi-scan SADABS2014/5 (Bruker,2014/5) was used for absorption correction. wr2(int) was 0.1351 before and 0.0522 after correction. The Ratio of minimum to maximum transmission is 0.9050. The /2 correction factor is 0.00150. T min, T max 0.675, 0.746 0.535, 0.746 No. of measured, independent and observed [I > 2 (I)] reflections 14261, 3686, 2869 6795, 2401, 1069 R int 0.043 0.103 (sin / ) max (Å -1 ) 0.595 0.595 Refinement R[F 2 > 2 (F 2 )], wr(f 2 ), S 0.039, 0.103, 1.04 0.066, 0.167, 0.92 No. of reflections 3686 2401 No. of parameters 268 207 Multi-scan SADABS2014/5 (Bruker,2014/5) was used for absorption correction. wr2(int) was 0.1810 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.7174. The /2 correction factor is 0.00150. H-atom treatment H-atom parameters constrained H atoms treated by a mixture of independent and constrained refinement max, min (e Å -3 ) 0.23, -0.35 0.30, -0.30

Biofilm inhibition activity in P. aeruginosa Fig. 5 Inhibition of biofilm formation in P. aeruginosa after 24 h treatment with 250 μm of glyoxamide compounds. The control represents the biofilms formation without any compounds. Error bars indicate the standard error of the mean (SEM) of three independent experiments. Biofilm inhibition activity in E. coli Fig. 6 Inhibition of biofilm formation in E. coli after 24 h treatment with 250 μm of glyoxamide compounds. The control represents the biofilms formation without any compounds. Error bars indicate the standard error of the mean (SEM) of three independent experiments.

Toxicity against human MRC-5 lung fibroblast cells Toxicity against MRC-5 human cells % of cell proliferation 100 50 12 19 27 30 0 10 1 10 2 10 3 Drug concentration [ M] Fig. 7 In vitro anti-proliferative properties of compounds 12, 19, 27, and 30 against MRC-5 normal human lung fibroblasts after 72 h incubation, relative to a DMSO control. The points represent the mean of at least three individual experiments ± standard error of the mean (SEM). Fig. 8 The bar graph represents the IC 50 of some of the active compounds 12, 19, 27, and 30 against MRC-5 normal human lung fibroblast cells. The concentration of compounds was tested between 100-750 µm. Error bars represent the mean of minimum three independent experiments ± Standard error of the mean (SEM).

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