Supplementary Information

Synthesis, Characterizations and Theoretical Calculations of 1,2-Diaminocyclohexane(1,3-Propylenediamine)gold(III) Complexes: In vitro Cytotoxic Evaluations against Human Cancer Cell Lines

Said S. Al-Jaroudi,a Muhammad Altaf,b A. Aziz Al-Saadi,a Abdel-NasserKawde,a Saleh Altuwaijri,c Saeed Ahmadd and Anvarhusein A. Isaba*

a Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran 31261, Saudi Arabia.

bCenter of Excellence, Nano Center Technology (CENT), King Fahd University of Petroleum and Minerals, Dhahran 31261, Saudi Arabia.

c Clinical Research Laboratory, SAAD Research Development Center, SAAD Specialist Hospital, Al-Khobar 31952, Saudi Arabia

d Department of Chemistry, University of Engineering and Technology, Lahore 54890, Pakistan

Table S1.λmax values derived from UV-Vis spectra for Au(III) complexes 1, 2 and 3.

Complex / λmax (nm)
NaAuCl4 / 293
(1) / 332
(2) / 339
(3) / 341
Compound 1
Bond Length (Å), found [Calc.] / Bond Angles (°), found [Calc.]
Au1—N1 / 2.03(3) [2.147]
Au1—N1i / 2.03(3)[2.147]
Au1—N2i / 2.01(3) [2.138]
Au1—N2 / 2.01(3) [2.137]
N1—C1 / 1.54(6) [1.537]
N2—C3 / 1.48(6) [1.545]
/ N1—Au1—N1i / 87(2) [88.9]
N1—Au1—N2i / 177.8(15) [174.2]
N1i—Au1—N2i / 93.2(15) [96.9]
N1—Au1—N2 / 93.2(15) [96.9]
N1i—Au1—N2 / 177.8(15) [174.2]
N2i—Au1—N2 / 87(2) [76.3]
C1—N1—Au1 / 113(2) [115.9]
C3—N2—Au1 / 109(3) [111.3]

Table S2. Selected bond distances and bond angles for complex 1.

TableS3. Relative energies (kcal/mol) of the four possible conformations of the [(DACH)Au(pn)]3+ complex.

Conformation / Relative Energy (kcal/mol)
a , b / 0.00
c / 3.31
d / 3.59

Table S4. The reduction peak potential of complex 3 in absence and presence of

different concentrations of lysozyme and BSA model proteins.

1 mM Complex 3 with / Ep(V)
0.0 µM Protein / -0.205
0.7 µM Lysozyme / -0.222
7.0 µMLysozyme / -0.270
35 µM Lysozyme / -0.303
7.5 µMBSA / -0.255
15 µMBSA / -0.256

FigureS1. View of the hydrogen bonded networkof compound 1 along plane caxis of the unit cell. Blue doted lines show hydrogen bonds between different functional groups of molecules.

FigureS2.Effect of cis-1,2-(DACH)gold(III)(pn)complex on cell growth in (A) PC-3 and (B) SGC-7901 cells. The cells were treated with 10 µM of the compound (1) for 1 day and 3 days. The anti-proliferative effect was measured by MTT assay. Results were expressed as the mean, SD. *P<0.05.

FigureS3.Effect of trans-(±)-1,2-(DACH)gold(III)(pn) complex on cell growth in (A) PC-3 and (B) SGC-7901 cells. The cells were treated with 10 µM of the compound (2) for 1 day and 3 days. The anti-proliferative effect was measured by MTT assay. Results were expressed as the mean, SD. *P<0.05.

FigureS4.Effect of cis-1,2-(DACH)gold(III)(pn) complex on cell growth in (A) PC-3 and (B) SGC-7901 cells. The cells were treated with various concentrations of the compound (1) for 24 h. The anti-proliferative effect was measured by MTT assay. Results were expressed as the mean, SD. *P<0.05.

FigureS5. Effect of trans-(±)-1,2-(DACH)gold(III)(pn) complex on cell growth in (A) PC-3 and (B) SGC-7901 cells. The cells were treated with various concentrations of the compound (2) for 24 h. The anti-proliferative effect was measured by MTT assay. Results were expressed as the mean, SD. *P<0.05.

Figure S6. UV-Vis spectra of complexes 1, 2 and 3 followed by dissolution in the buffer solution at 37 oC (a) just after mixing and (b) after 3 days.

FigureS7. The 500-MHz 1H solution state NMR spectrum of [{(1S,2S)-(+)-1,2-(DACH)}Au(pn)]Cl3 complex.

FigureS8. The 125.65-MHz 13C{1H} solution state NMR spectrum of [{(1S,2S)-(+)-1,2-(DACH)}Au(pn)]Cl3 complex.

a / b
c / d

Figure S9. Four possible [(DACH)Au(pn)]3+ configurations optimized at the B3LYP/LANL2DZ level of theory. The two trans configurations labeled a and b are mirror images. Forms c and d maintains DACH in a cis configuration.

Figure S10. Solution state 1H NMR spectrum of [{(1S,2S)-(+)-1,2-(DACH)}Au(pn)]Cl3complex in D2O (a) just after mixing and (b) after 7 days .

Figure S11. Solution state 13C{1H} NMR spectrum of [{(1S,2S)-(+)-1,2-(DACH)}Au(pn)]Cl3complex in D2O (a) just after mixing and (b) after 7 days.

Figure S12. Solution state 1H NMR spectrum of [{(1S,2S)-(+)-1,2-(DACH)}Au(pn)]Cl3complex in DMSO-d6/D2O (a) just after mixing and (b) after 7 days .

Figure S13. Solution state 13C{1H} NMR spectrum of [{(1S,2S)-(+)-1,2-(DACH)}Au(pn)]Cl3complex in DMSO-d6/D2O (a) just after mixing and (b) after 7 days.

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