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Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) Cyclopentadienyl iron dicarbonyl (CpFe(CO) 2 ) derivatives as apoptosis-inducing agents H.T. Poh a, P.C. Ho b,and Wai Yip Fan a,* a Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 b Division of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543. *Corresponding author: Fax : (+65) 67791691. E-mail: chmfanwy@nus.edu.sg Table of contents: 1. IC 50 Curves for MDA-MB-231 Cell Line 2. IC 50 Curves for HeLa Cell Line 3. Flow Cytometry Dot Plots (MDA-MB-231) 4. Flow Cytometry Dot Plots (HeLa) 5. Flow Cytometry Dot Plots (MCF-10A) 6. Confocal Images for MDA-MB-231 Cell Line 7. X-ray structural reports for CpFe(CO) 2 (SCN), 4 and CpFe(CO) 2 (NCS), 5 1

1. IC 50 Curve for MDA-MB-231 Cell Line IC 50 curves for CpFe(CO) 2 complexes 1 to 7. MTS measurements were made on the MDA-MB- 231 cell line after 24 hour treatment with the respective complexes at 37 C. 2

2. IC 50 Curve for HeLa Cell Line IC 50 curves for CpFe(CO) 2 complexes 1 to 7. MTS measurements were made on the HeLa cell line after 24 hour treatment with the respective complexes at 37 C. 3

3. Flow Cytometry Dot Plots (MDA-MB-231) Detection of early and late apoptotic MDA-MB-231 cells after staining with Annexin V- Alexa Fluor 488 and PI. Cells were incubated for 24 h with 0 M (control), 5 M and 10 μm solutions of complex 3 before staining. Detection of early and late apoptotic MDA-MB-231 cells after staining with Annexin V- Alexa Fluor 488 and PI. Cells were incubated for 24 h with 0 M (control), 5 M and 10 μm solutions of complex 6 before staining. 4

Detection of early and late apoptotic MDA-MB-231 cells after staining with Annexin V- Alexa Fluor 488 and PI. Cells were incubated for 24 h with 0 M (control), 5 M and 10 μm solutions of complex 7 before staining. 5

4. Flow Cytometry Dot Plots (HeLa) Detection of early and late apoptotic HeLa cells after staining with Annexin V-Alexa Fluor 488 and PI. Cells were incubated for 24 h with 0 M (control), 5 M and 10 μm solutions of complex 3 before staining. Detection of early and late apoptotic HeLa cells after staining with Annexin V-Alexa Fluor 488 and PI. Cells were incubated for 24 h with 0 M (control), 5 M and 10 μm solutions of complex 6 before staining. 6

Detection of early and late apoptotic HeLa cells after staining with Annexin V-Alexa Fluor 488 and PI. Cells were incubated for 24 h with 0 M (control), 5 M and 10 μm solutions of complex 7 before staining. 7

5. Flow Cytometry Dot Plots (MCF-10A) Detection of early and late apoptotic MCF-10A normal mammary cells after staining with Annexin V-Alexa Fluor 488 and PI. Cells were incubated for 24 h with 0 M (control), 5 M and 10 M solutions of complex 3 before staining. Detection of early and late apoptotic MCF-10A normal mammary cells after staining with Annexin V-Alexa Fluor 488 and PI. Cells were incubated for 24 h with 0 M (control), 5 M and 10 μm solutions of complex 6 before staining. 8

Detection of early and late apoptotic MCF-10A normal mammary cells after staining with Annexin V-Alexa Fluor 488 and PI. Cells were incubated for 24 h with 0 M (control), 5 M and 10 μm solutions of complex 7 before staining. 9

6. Confocal Images for MDA-MB-231 Cell Line Annexin V (green) and PI (red) stained MDA-MB-231 cells after treatment with 0 μm (control), 5 μm, 10 μm and 20 μm of complex 4 at 37 C for 24 hours. 10

Annexin V (green) and PI (red) stained MDA-MB-231 cells after treatment with 0 μm (control), 5 μm, 10 μm and 20 μm of complex 5 at 37 C for 24 hours.. 11

Annexin V (green) and PI (red) stained MDA-MB-231 cells after treatment with 0 μm (control), 5 μm, 10 μm and 20 μm of complex 6 at 37 C for 24 hours. 12

Annexin V (green) and PI (red) stained MDA-MB-231 cells after treatment with 0 μm (control), 5 μm, 10 μm and 20 μm of complex 7 at 37 C for 24 hours. 13

7. Confocal Images for HeLa Cell Line Annexin V (green) and PI (red) stained HeLa cells after treatment with 0 μm (control), 5 μm, 10 μm and 20 μm of complex 4 at 37 C for 24 hours. 14

Annexin V (green) and PI (red) stained HeLa cells after treatment with 0 μm (control), 5 μm, 10 μm and 20 μm of complex 5 at 37 C for 24 hours. 15

Annexin V (green) and PI (red) stained HeLa cells after treatment with 0 μm (control), 5 μm, 10 μm and 20 μm of complex 6 at 37 C for 24 hours. 16

Annexin V (green) and PI (red) stained HeLa cells after treatment with 0 μm (control), 5 μm, 10 μm and 20 μm of complex 7 at 37 C for 24 hours. 17

8. X-ray structural reports for CpFe(CO) 2 (SCN), 4 and CpFe(CO) 2 (NCS), 5 CpFe(CO) 2 (SCN), 4 Table 1. Crystal data and structure refinement for C790. Identification code Empirical formula c790 Formula weight 235.04 Temperature Wavelength Crystal system Space group P-1 C8 H5 Fe N O2 S 100(2) K 0.71073 Å Triclinic Unit cell dimensions a = 6.798(4) Å a= 93.169(7). b = 7.024(4) Å b= 95.036(7). c = 10.813(6) Å g = 118.514(7). Volume 449.1(4) Å 3 Z 2 Density (calculated) 1.738 Mg/m 3 Absorption coefficient 1.871 mm -1 F(000) 236 Crystal size 0.40 x 0.26 x 0.10 mm 3 Theta range for data collection 1.90 to 27.50. Index ranges Reflections collected 4151-8<=h<=8, -9<=k<=9, -14<=l<=14 Independent reflections 2052 [R(int) = 0.0515] Completeness to theta = 27.50 99.3 % Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.7457 and 0.5570 Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 2052 / 0 / 118 Goodness-of-fit on F 2 1.065 Final R indices [I>2sigma(I)] R1 = 0.0533, wr2 = 0.1200 R indices (all data) R1 = 0.0738, wr2 = 0.1469 Largest diff. peak and hole 0.932 and -0.803 e.å -3 18

Table 2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ) for C790. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq) Fe(1) 5305(1) 2275(1) 2345(1) 10(1) S(1) 3906(2) -1262(2) 1484(1) 17(1) O(1) 1895(6) 898(6) 4058(3) 23(1) O(2) 2515(7) 3033(7) 435(4) 28(1) N(1) 3899(8) -3427(8) 3640(4) 23(1) C(1) 7645(8) 4815(8) 3658(5) 16(1) C(2) 7870(9) 5491(9) 2433(5) 21(1) C(3) 8446(8) 4115(9) 1697(5) 17(1) C(4) 8586(9) 2631(9) 2479(5) 20(1) C(5) 8068(8) 3019(8) 3681(5) 17(1) C(6) 3916(8) -2506(8) 2776(5) 15(1) C(7) 3219(8) 1435(8) 3394(4) 13(1) C(8) 3615(9) 2715(8) 1168(5) 17(1) 19

Table 3. Bond lengths [Å] and angles [ ] for C790. Fe(1)-C(8) 1.778(5) Fe(1)-C(7) 1.789(5) Fe(1)-C(2) 2.083(5) Fe(1)-C(1) 2.084(5) Fe(1)-C(5) 2.096(5) Fe(1)-C(3) 2.109(5) Fe(1)-C(4) 2.114(5) Fe(1)-S(1) 2.2970(18) S(1)-C(6) 1.690(5) O(1)-C(7) 1.135(6) O(2)-C(8) 1.146(6) N(1)-C(6) 1.163(7) C(1)-C(5) 1.422(7) C(1)-C(2) 1.428(7) C(1)-H(1) 1.0000 C(2)-C(3) 1.432(8) C(2)-H(2) 1.0000 C(3)-C(4) 1.410(7) C(3)-H(3) 1.0000 C(4)-C(5) 1.422(7) C(4)-H(4) 1.0000 C(5)-H(5) 1.0000 C(8)-Fe(1)-C(7) 93.9(2) C(8)-Fe(1)-C(2) 91.3(2) C(7)-Fe(1)-C(2) 122.0(2) C(8)-Fe(1)-C(1) 121.2(2) C(7)-Fe(1)-C(1) 91.4(2) C(2)-Fe(1)-C(1) 40.1(2) C(8)-Fe(1)-C(5) 158.1(2) C(7)-Fe(1)-C(5) 96.8(2) C(2)-Fe(1)-C(5) 66.9(2) C(1)-Fe(1)-C(5) 39.8(2) C(8)-Fe(1)-C(3) 97.6(2) 20

C(7)-Fe(1)-C(3) 158.5(2) C(2)-Fe(1)-C(3) 40.0(2) C(1)-Fe(1)-C(3) 67.1(2) C(5)-Fe(1)-C(3) 66.8(2) C(8)-Fe(1)-C(4) 133.4(2) C(7)-Fe(1)-C(4) 132.7(2) C(2)-Fe(1)-C(4) 65.9(2) C(1)-Fe(1)-C(4) 66.2(2) C(5)-Fe(1)-C(4) 39.5(2) C(3)-Fe(1)-C(4) 39.0(2) C(8)-Fe(1)-S(1) 90.99(17) C(7)-Fe(1)-S(1) 91.22(16) C(2)-Fe(1)-S(1) 146.40(17) C(1)-Fe(1)-S(1) 147.46(15) C(5)-Fe(1)-S(1) 107.74(15) C(3)-Fe(1)-S(1) 106.59(15) C(4)-Fe(1)-S(1) 88.71(15) C(6)-S(1)-Fe(1) 100.96(17) C(5)-C(1)-C(2) 107.8(4) C(5)-C(1)-Fe(1) 70.5(3) C(2)-C(1)-Fe(1) 69.9(3) C(5)-C(1)-H(1) 126.1 C(2)-C(1)-H(1) 126.1 Fe(1)-C(1)-H(1) 126.1 C(1)-C(2)-C(3) 108.3(5) C(1)-C(2)-Fe(1) 70.0(3) C(3)-C(2)-Fe(1) 71.0(3) C(1)-C(2)-H(2) 125.8 C(3)-C(2)-H(2) 125.8 Fe(1)-C(2)-H(2) 125.8 C(4)-C(3)-C(2) 106.9(5) C(4)-C(3)-Fe(1) 70.7(3) C(2)-C(3)-Fe(1) 69.0(3) C(4)-C(3)-H(3) 126.5 C(2)-C(3)-H(3) 126.5 Fe(1)-C(3)-H(3) 126.5 21

C(3)-C(4)-C(5) 109.5(5) C(3)-C(4)-Fe(1) 70.3(3) C(5)-C(4)-Fe(1) 69.6(3) C(3)-C(4)-H(4) 125.2 C(5)-C(4)-H(4) 125.2 Fe(1)-C(4)-H(4) 125.2 C(4)-C(5)-C(1) 107.4(4) C(4)-C(5)-Fe(1) 70.9(3) C(1)-C(5)-Fe(1) 69.7(3) C(4)-C(5)-H(5) 126.3 C(1)-C(5)-H(5) 126.3 Fe(1)-C(5)-H(5) 126.3 N(1)-C(6)-S(1) 177.7(5) O(1)-C(7)-Fe(1) 179.9(5) O(2)-C(8)-Fe(1) 178.1(5) Symmetry transformations used to generate equivalent atoms: 22

Table 4. Anisotropic displacement parameters (Å 2 x 10 3 ) for C790. The anisotropic displacement factor exponent takes the form: -2p 2 [ h 2 a* 2 U 11 +... + 2 h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 Fe(1) 10(1) 11(1) 4(1) 1(1) -1(1) 2(1) S(1) 23(1) 13(1) 8(1) -1(1) -1(1) 3(1) O(1) 21(2) 33(2) 12(2) 5(2) 8(2) 9(2) O(2) 27(2) 47(3) 15(2) 13(2) 0(2) 20(2) N(1) 26(3) 24(2) 18(2) 5(2) 2(2) 12(2) C(1) 16(3) 11(2) 11(2) -3(2) 0(2) 0(2) C(2) 13(2) 15(3) 24(3) 7(2) -3(2) -1(2) C(3) 9(2) 23(3) 9(2) 3(2) 1(2) -1(2) C(4) 15(3) 26(3) 14(2) -1(2) 0(2) 6(2) C(5) 10(2) 17(3) 17(3) 4(2) -6(2) 2(2) C(6) 16(2) 9(2) 16(3) -2(2) 0(2) 5(2) C(7) 16(3) 14(2) 4(2) -1(2) -3(2) 4(2) C(8) 19(3) 14(2) 21(3) 7(2) 6(2) 9(2) Table 5. Hydrogen coordinates ( x 10 4 ) and isotropic displacement parameters (Å 2 x 10 3 ) for C790. x y z U(eq) H(1) 7290 5504 4377 19 H(2) 7692 6735 2145 25 H(3) 8733 4214 805 20 H(4) 8953 1459 2221 24 H(5) 8057 2213 4416 20 23

CpFe(CO) 2 (NCS), 5 Table 1. Crystal data and structure refinement for C532. Identification code Empirical formula c532 Formula weight 235.04 Temperature Wavelength Crystal system Space group C8 H5 Fe N O2 S 100(2) K 0.71073 Å Monoclinic P2(1)/m Unit cell dimensions a = 6.3240(10) Å a= 90. b = 8.9082(14) Å b= 91.684(4). c = 7.8468(12) Å g = 90. Volume 441.86(12) Å 3 Z 2 Density (calculated) 1.767 Mg/m 3 Absorption coefficient 1.902 mm -1 F(000) 236 Crystal size 0.20 x 0.11 x 0.05 mm 3 Theta range for data collection 2.60 to 27.50. Index ranges Reflections collected 3137-7<=h<=8, -11<=k<=11, -9<=l<=10 Independent reflections 1075 [R(int) = 0.0322] Completeness to theta = 27.50 99.1 % Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.9109 and 0.7022 Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 1075 / 0 / 67 Goodness-of-fit on F 2 1.236 Final R indices [I>2sigma(I)] R1 = 0.0310, wr2 = 0.0783 R indices (all data) R1 = 0.0405, wr2 = 0.1073 Largest diff. peak and hole 0.647 and -0.688 e.å -3 24

Table 2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ) for C532. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq) Fe(1) 674(1) 2500 1677(1) 11(1) S(1) -3062(2) 2500-3619(1) 19(1) O(1) -1864(3) 26(2) 3000(3) 22(1) N(1) -857(5) 2500-481(4) 16(1) C(1) 3507(6) 2500 301(5) 17(1) C(2) 3410(4) 1206(3) 1345(4) 17(1) C(3) 3288(4) 1702(3) 3076(4) 19(1) C(4) -916(4) 996(3) 2500(3) 16(1) C(5) -1746(6) 2500-1793(5) 14(1) 25

Table 3. Bond lengths [Å] and angles [ ] for C532. Fe(1)-C(4) 1.806(3) Fe(1)-C(4)#1 1.806(3) Fe(1)-N(1) 1.925(4) Fe(1)-C(3)#1 2.083(3) Fe(1)-C(3) 2.083(3) Fe(1)-C(2)#1 2.102(3) Fe(1)-C(2) 2.102(3) Fe(1)-C(1) 2.118(4) S(1)-C(5) 1.636(4) O(1)-C(4) 1.128(4) N(1)-C(5) 1.159(5) C(1)-C(2)#1 1.416(4) C(1)-C(2) 1.416(4) C(2)-C(3) 1.433(4) C(3)-C(3)#1 1.422(6) C(4)-Fe(1)-C(4)#1 95.80(17) C(4)-Fe(1)-N(1) 92.50(11) C(4)#1-Fe(1)-N(1) 92.50(11) C(4)-Fe(1)-C(3)#1 120.42(12) C(4)#1-Fe(1)-C(3)#1 89.99(12) N(1)-Fe(1)-C(3)#1 146.56(11) C(4)-Fe(1)-C(3) 89.99(12) C(4)#1-Fe(1)-C(3) 120.42(12) N(1)-Fe(1)-C(3) 146.56(11) C(3)#1-Fe(1)-C(3) 39.91(16) C(4)-Fe(1)-C(2)#1 156.97(12) C(4)#1-Fe(1)-C(2)#1 96.10(12) N(1)-Fe(1)-C(2)#1 106.59(11) C(3)#1-Fe(1)-C(2)#1 40.05(11) C(3)-Fe(1)-C(2)#1 66.98(11) C(4)-Fe(1)-C(2) 96.10(12) C(4)#1-Fe(1)-C(2) 156.97(12) N(1)-Fe(1)-C(2) 106.59(11) 26

C(3)#1-Fe(1)-C(2) 66.98(11) C(3)-Fe(1)-C(2) 40.05(11) C(2)#1-Fe(1)-C(2) 66.53(15) C(4)-Fe(1)-C(1) 132.08(9) C(4)#1-Fe(1)-C(1) 132.08(9) N(1)-Fe(1)-C(1) 87.88(15) C(3)#1-Fe(1)-C(1) 66.33(13) C(3)-Fe(1)-C(1) 66.33(13) C(2)#1-Fe(1)-C(1) 39.22(9) C(2)-Fe(1)-C(1) 39.22(9) C(5)-N(1)-Fe(1) 178.9(3) C(2)#1-C(1)-C(2) 109.0(4) C(2)#1-C(1)-Fe(1) 69.75(18) C(2)-C(1)-Fe(1) 69.75(18) C(1)-C(2)-C(3) 107.5(3) C(1)-C(2)-Fe(1) 71.03(19) C(3)-C(2)-Fe(1) 69.27(15) C(3)#1-C(3)-C(2) 107.97(17) C(3)#1-C(3)-Fe(1) 70.05(8) C(2)-C(3)-Fe(1) 70.68(16) O(1)-C(4)-Fe(1) 177.9(2) N(1)-C(5)-S(1) 178.5(4) Symmetry transformations used to generate equivalent atoms: #1 x,-y+1/2,z 27

Table 4. Anisotropic displacement parameters (Å 2 x 10 3 ) for C532. The anisotropic displacement factor exponent takes the form: -2p 2 [ h 2 a* 2 U 11 +... + 2 h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 Fe(1) 12(1) 11(1) 11(1) 0 0(1) 0 S(1) 26(1) 19(1) 13(1) 0-5(1) 0 O(1) 23(1) 17(1) 26(1) 1(1) 5(1) -5(1) N(1) 16(2) 16(2) 16(2) 0 0(1) 0 C(1) 12(2) 19(2) 20(2) 0 4(2) 0 C(2) 10(1) 17(1) 24(1) -2(1) 1(1) 2(1) C(3) 12(1) 24(2) 19(1) 4(1) -3(1) 1(1) C(4) 16(1) 18(1) 14(1) -2(1) 0(1) 4(1) C(5) 14(2) 10(2) 17(2) 0 3(2) 0 Table 5. Hydrogen coordinates ( x 10 4 ) and isotropic displacement parameters (Å 2 x 10 3 ) for C532. x y z U(eq) H(1) 3596 2500-969 21 H(2) 3455 140 948 20 H(3) 3248 1042 4106 22 28

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