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S1

Acridine-decorated cyclometallated gold(III) complexes: synthesis and anti-tumour investigations

Morwen R. M. Williams,a Benoît Bertrand,*a,b Julio Fernandez-Cestau,a Zoë A. E. Waller,c Maria A.

O’Connell,c Mark Searcey,*a,c and Manfred Bochmann*a

a School of Chemistry, University of East Anglia, Norwich, NR4 7TJ (UK)

Email: benoit.bertrand@upmc.frb Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire (IPCM), F-75005 Paris, Francec School of Pharmacy, University of East Anglia, Norwich, NR4 7TJ (UK)

Supporting informations

Contents Page

Figure S1: Correlation between IC50 and cell uptake of complexes 2, 6, 7 and 11 in MCF-7 cells.

S2

Figure S2: 1H NMR spectra of a 1:1 mixture of 7 with GSH at room temperature, in comparison with the starting materials, 7, GSH and GSSG (DMSO-d6/D2O 1:1).

S2

Figure S3-S17: NMR spectra of complexes 4, 6-11 S3-S16

Electronic Supplementary Material (ESI) for Dalton Transactions.This journal is © The Royal Society of Chemistry 2018

S2

Figure S1: Correlation between IC50 and cell uptake of complexes 2, 6, 7 and 11 in MCF-7 cells.

Figure S2: 1H NMR spectra of a 1:1 mixture of 7 with GSH at room temperature, in comparison with the starting materials, 7, GSH and GSSG (DMSO-d6/D2O 1:1).

S3

4

1 2

3

4567

8910

11 12

1314

1516

17

1819

20

NAu

tBu

N OO

Figure S3: 1H NMR spectrum of complex 4 in CD2Cl2.

S4

Figure S4: 13C{1H} NMR spectrum of complex 4 in CD2Cl2

S5

6

NAu

tBu

N NO O

1 2

3

4567

8910

11 12

13

14

151617

1819

20 22

21

Figure S5: 1H NMR spectrum of complex 6 in CD2Cl2.

S6

Figure S6: 13C{1H} NMR spectrum of complex 6 in CD2Cl2

Figure S7: 13C-1H HMQC spectrum of complex 6 in CD2Cl2 showing C20+22.

S7

7

NAu

tBu

N ON

1 2

3

4567

8910

1112

13

14

1516

17

18

19

20

2124

25

23 22

Figure S8: 1H NMR spectrum of complex 7 in CD2Cl2 (tert-Bu singlet at 0.35 ppm not shown).

S8

Figure S9: 13C{1H} NMR spectrum of complex 7 in CD2Cl2.

S9

8

AuN

ONN

1 23

45

67/7'

89

1011

12

13

14

15

1617

18

192021

24

2523

2226

Figure S10: 1H NMR spectrum of complex 8 in CD2Cl2 (263 K).

S10

Figure S11: 13C{1H} NMR spectrum of complex 8 in CD2Cl2.

S11

9

NAu

tBu

NHNN

12

3

4567

8910

11 12

13

14

15 16

17

18

19

2021

24

25

2322

Figure S12: 1H NMR spectrum of complex 9 in CD2Cl2 (tert-Bu singlet at 1.46 ppm not shown).

S12

Figure S13: 13C{1H} NMR spectrum of complex 9 in CD2Cl2.

S13

10

N

N

tBu tBuAu

SbF6

NHRHN

123 4

56

789

1011

1213

14

15

16 17

18

1920

21 22

2324

NR=

Figure S14: 1H NMR spectrum of complex 10 in (CD3)2SO.

S14

Figure S15: 13C{1H} NMR spectrum of complex 10 in (CD3)2SO.

S15

11

N

N

tBu tBuAu

PF6123 4 5

6

7

8910

11 12

13

1415

16

17 18

19

20

NR=

N NR

Figure S16: 1H NMR spectrum of complex 11 in CD3CN

S16

Figure S17: 13C{1H} NMR spectrum of complex 11 in CD3CN.

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