Table S1 Energy Components for the First Substitution of Trans-Pt Chloroaqua/Diaqua Trans

Theoretical study of DNA base guanine and adenine and protein residues binding mode of the trans geometries of new antitumor nonclassical platinum complexes containing pyridine and picoline ligand

Tian Li, Yan Gao, Juan Li, Lixin Zhou*

Department of Chemistry, Jinan University, Guangzhou, Guangdong 510632, P. R. China

*Corresponding author. E-mail:

Table S1 Energy components for the first substitution of trans-Pt chloroaqua/diaqua ®trans -monoadduct with guanine (G) or adenine (A) for trans-[PtCl2(NH3)(pyridine)]

state / ZPEa / E a / Ha / Ga / Egb / Gaqc
ClA•RC / 0.273607 / -1427.588335 / -1427.587390 / -1427.661930 / -1428.174737 / -1428.260095
ClA•TS1 / 0.272500 / -1427.549399 / -1427.548455 / -1427.622213 / -1428.136570 / -1428.220555
ClA•TS2 / 0.273007 / -1427.556805 / -1427.555861 / -1427.628851 / -1428.143527 / -1428.222976
ClA•PC1 / 0.273320 / -1427.599130 / -1427.598185 / -1427.672246 / -1428.191079 / -1428.271984
ClA•PC2 / 0.273427 / -1427.600168 / -1427.599224 / -1427.673014 / -1428.192099 / -1428.270910
ClG•RC / 0.277275 / -1502.842268 / -1502.841324 / -1502.914597 / -1503.462598 / -1503.550237
ClG•TS1 / 0.277556 / -1502.815147 / -1502.814203 / -1502.889474 / -1503.435804 / -1503.519378
ClG•TS2 / 0.277657 / -1502.815150 / -1502.814205 / -1502.889205 / -1503.435839 / -1503.519298
ClG•PC1 / 0.277641 / -1502.846910 / -1502.845965 / -1502.923451 / -1503.471860 / -1503.557565
ClG•PC2 / 0.277603 / -1502.846928 / -1502.845984 / -1502.923481 / -1503.471928 / -1503.557649
WA•RC / 0.299524 / -1043.448364 / -1043.447420 / -1043.521770 / -1044.050270 / -1044.296215
WA•TS1 / 0.296888 / -1043.395022 / -1043.394077 / -1043.467986 / -1043.992997 / -1044.254007
WA•TS2 / 0.296888 / -1043.395022 / -1043.394078 / -1043.467989 / -1043.992995 / -1044.253948
WA•PC1 / 0.297338 / -1043.446011 / -1043.445067 / -1043.520795 / -1044.052073 / -1044.306797
WA•PC2 / 0.299271 / -1043.462657 / -1043.461712 / -1043.534796 / -1044.066070 / -1044.313993
WG•RC / 0.302188 / -1118.709850 / -1118.708905 / -1118.788770 / -1119.347748 / -1119.585865
WG•TS1 / 0.302297 / -1118.667530 / -1118.666586 / -1118.741174 / -1119.300215 / -1119.549011
WG•TS2 / 0.302639 / -1118.669878 / -1118.668933 / -1118.743291 / -1119.302312 / -1119.550430
WG•PC1 / 0.303964 / -1118.722591 / -1118.721647 / -1118.796619 / -1119.360487 / -1119.598459
WG•PC2 / 0.303866 / -1118.721062 / -1118.720118 / -1118.795187 / -1119.359048 / -1119.598459

aCalculated values at the B3LYP/(LanL2DZ+6-31G(d,p)) level. bSingle-point energies at the B3LYP/(LanL2DZ+6- 311++G(2d,2p)) level. cEnergies in the aqueous phase at the B3LYP/(LanL2DZ+6-311++G(2d,2p)) level. The suffix g and aq means gas phase and aqua phase respectively. All energy values in a.u..

Table S2 Energy components for the first substitution of trans-Pt chloroaqua/diaqua ® trans-monoadduct with guanine (G) or adenine (A) for trans-[PtCl2(pyridine)2]

state / ZPEa / Ea / Ha / Ga / Egb / Gaqc
ClA•RC / 0.325571 / -1619.257477 / -1619.256533 / -1619.340648 / -1619.947949 / -1620.014378
ClA•TS1 / 0.324645 / -1619.232868 / -1619.231924 / -1619.312196 / -1619.922620 / -1619.990158
ClA•TS2 / 0.324646 / -1619.232868 / -1619.231924 / -1619.312194 / -1619.922619 / -1619.990155
ClA•PC1 / 0.323426 / -1619.264685 / -1619.263741 / -1619.347961 / -1619.962153 / -1620.031352
ClA•PC2 / 0.324327 / -1619.275984 / -1619.275040 / -1619.357331 / -1619.971070 / -1620.035943
ClG•RC / 0.329902 / -1694.512339 / -1694.511395 / -1694.597508 / -1695.237779 / -1695.310059
ClG•TS1 / 0.328165 / -1694.481579 / -1694.480635 / -1694.565093 / -1695.206368 / -1695.281999
ClG•TS2 / 0.327487 / -1694.471842 / -1694.470898 / -1694.556544 / -1695.198222 / -1695.273764
ClG•PC1 / 0.328660 / -1694.511739 / -1694.510795 / -1694.596719 / -1695.239960 / -1695.317052
ClG•PC2 / 0.328341 / -1694.515088 / -1694.514144 / -1694.600637 / -1695.245596 / -1695.316201
WA•RC / 0.349693 / -1235.127947 / -1235.127003 / -1235.210734 / -1235.833992 / -1236.058984
WA•TS / 0.348642 / -1235.084507 / -1235.083563 / -1235.164778 / -1235.785344 / -1236.019810
WA•PC / 0.350128 / -1235.136152 / -1235.135208 / -1235.217170 / -1235.842995 / -1236.067978
WG•RC / 0.353724 / -1310.387816 / -1310.386872 / -1310.473687 / -1311.127582 / -1311.347894
WG•TS / 0.353097 / -1310.353200 / -1310.352256 / -1310.436084 / -1311.089724 / -1311.317757
WG•PC / 0.354643 / -1310.406934 / -1310.405990 / -1310.490275 / -1311.148333 / -1311.365680

Table S3 Energy components for the first substitution of trans-Pt chloroaqua/diaqua ®trans -monoadduct with guanine (G) or adenine (A) for trans-[PtCl2(NH3)(2-picoline)]
state / ZPEa / E a / Ha / Ga / Egb / Gaqc
ClA•RC / 0.301264 / -1466.902703 / -1466.879701 / -1466.957698 / -1467.506103 / -1467.57955
ClA•TS1 / 0.300481 / -1466.873229 / -1466.850328 / -1466.926654 / -1467.4766692 / -1467.550139
ClA•TS2 / 0.300081 / -1466.870767 / -1466.847578 / -1466.924704 / -1467.474147 / -1467.551142
ClA•PC1 / 0.300981 / -1466.914051 / -1466.890496 / -1466.967611 / -1467.5223315 / -1467.597575
ClA•PC2 / 0.301137 / -1466.920895 / -1466.897447 / -1466.973311 / -1467.5278554 / -1467.598213
ClG•RC / 0.304963 / -1542.157628 / -1542.133735 / -1542.213262 / -1542.7951322 / -1542.871428
ClG•TS1 / 0.304541 / -1542.126968 / -1542.102422 / -1542.181325 / -1542.7626125 / -1542.841768
ClG•TS2 / 0.303154 / -1542.11347 / -1542.088071 / -1542.169661 / -1542.7505898 / -1542.83356
ClG•PC1 / 0.305262 / -1542.164976 / -1542.139958 / -1542.220123 / -1542.8045639 / -1542.884324
ClG•PC2 / 0.304556 / -1542.162468 / -1542.137011 / -1542.218736 / -1542.8027285 / -1542.881690
WA•RC / 0.32649 / -1082.763449 / -1082.739663 / -1082.818199 / -1083.3811016 / -1083.620332
WA•TS1 / 0.324202 / -1082.707915 / -1082.68408 / -1082.760932 / -1083.3225302 / -1083.576610
WA•TS2 / 0.324564 / -1082.711415 / -1082.687818 / -1082.764393 / -1083.3254681 / -1083.578744
WA•PC1 / 0.326756 / -1082.780546 / -1082.756945 / -1082.833316 / -1083.399909 / -1083.638762
WA•PC2 / 0.32679 / -1082.781268 / -1082.757685 / -1082.833856 / -1083.4002402 / -1083.641451
WG•RC / 0.329742 / -1158.028807 / -1158.003333 / -1158.085798 / -1158.6805795 / -1158.911451
WG•TS1 / 0.328598 / -1157.980354 / -1157.955296 / -1158.03532 / -1158.628497 / -1158.871615
WG•TS2 / 0.328559 / -1157.982221 / -1157.956942 / -1158.036497 / -1158.6306983 / -1158.868664
WG•PC1 / 0.331241 / -1158.041392 / -1158.016557 / -1158.095094 / -1158.6938502 / -1158.924564
WG•PC2 / 0.330624 / -1158.044288 / -1158.019080 / -1158.100021 / -1158.6967926 / -1158.928430

aCalculated values at the B3LYP/(LanL2DZ+6-31G(d,p)) level. bSingle-point energies at the B3LYP/(LanL2DZ+6-311++G(2d,2p)) level. cEnergies in the aqueous phase at the B3LYP/ (LanL2DZ+6-311 ++G(2d,2p)) level. The suffix g and aq means gas phase and aqua phase respectively. All energy values in a.u..

Table S4 Energy components for the first substitution of trans-Pt chloroaqua/diaqua ®trans -monoadduct with guanine (G) or adenine (A) for trans-[PtCl2(NH3)(3-picoline)]

state / ZPEa / E a / Ha / Ga / Egb / Gaqc
ClA•RC / 0.301109 / -1466.903684 / -1466.880559 / -1466.958812 / -1467.5070346 / -1467.582137
ClA•TS1 / 0.300164 / -1466.874422 / -1466.851179 / -1466.92903 / -1467.4775861 / -1467.551852
ClA•TS2 / 0.300065 / -1466.871451 / -1466.848062 / -1466.926685 / -1467.474754 / -1467.549031
ClA•PC1 / 0.300867 / -1466.915624 / -1466.891816 / -1466.970452 / -1467.5240862 / -1467.597176
ClA•PC2 / 0.301012 / -1466.921106 / -1466.897365 / -1466.975163 / -1467.528397 / -1467.597751
ClG•RC / 0.306067 / -1542.160633 / -1542.136593 / -1542.217617 / -1542.7966142 / -1542.871421
ClG•TS1 / 0.305154 / -1542.131329 / -1542.106952 / -1542.185988 / -1542.7677357 / -1542.844303
ClG•TS2 / 0.305153 / -1542.131331 / -1542.106953 / -1542.18599 / -1542.7677395 / -1542.844373
ClG•PC1 / 0.304969 / -1542.164547 / -1542.139213 / -1542.221427 / -1542.8041196 / -1542.883119
ClG•PC2 / 0.304505 / -1542.161709 / -1542.136056 / -1542.21949 / -1542.8023791 / -1542.880314
WA•RC / 0.32631 / -1082.764605 / -1082.740578 / -1082.820897 / -1083.382292 / -1083.620353
WA•TS1 / 0.324442 / -1082.71127 / -1082.687372 / -1082.764882 / -1083.3263091 / -1083.579737
WA•TS2 / 0.324483 / -1082.715067 / -1082.691235 / -1082.769127 / -1083.3293998 / -1083.574782
WA•PC1 / 0.326549 / -1082.781618 / -1082.757807 / -1082.835503 / -1083.4012802 / -1083.639853
WA•PC2 / 0.326752 / -1082.78307 / -1082.759342 / -1082.836374 / -1083.4024115 / -1083.64346
WG•RC / 0.329386 / -1158.029547 / -1158.003771 / -1158.088369 / -1158.6816868 / -1158.910925
WG•TS1 / 0.328548 / -1157.986314 / -1157.961115 / -1158.042428 / -1158.6348321 / -1158.87258
WG•TS2 / 0.32858 / -1157.981343 / -1157.956061 / -1158.036502 / -1158.6307537 / -1158.872919
WG•PC1 / 0.331483 / -1158.042244 / -1158.017367 / -1158.096527 / -1158.6955148 / -1158.924429
WG•PC2 / 0.330931 / -1158.045844 / -1158.020689 / -1158.101283 / -1158.6989927 / -1158.931145

aCalculated values at the B3LYP/(LanL2DZ+6-31G(d,p)) level. bSingle-point energies at the B3LYP/(LanL2DZ+6-311++G(2d,2p)) level. cEnergies in the aqueous phase at the B3LYP/(LanL2DZ+6-311++G(2d,2p)) level. The suffix g and aq means gas phase and aqua phase respectively. All energy values in a.u..

Table S5 Energy components for the first substitution of trans-Pt chloroaqua/diaqua ®trans -monoadduct with guanine (G) or adenine (A) for trans-[PtCl2(NH3)(4-picoline)]

state / ZPEa / E a / Ha / Ga / Egb / Gaqc
ClA•RC / 0.300811 / -1466.905974 / -1466.883619 / -1466.960106 / -1467.5091172 / -1467.584378
ClA•TS1 / 0.300157 / -1466.876259 / -1466.852965 / -1466.9313 / -1467.4795596 / -1467.553915
ClA•TS2 / 0.300105 / -1466.872999 / -1466.849636 / -1466.927955 / -1467.4763476 / -1467.550874
ClA•PC1 / 0.300673 / -1466.91847 / -1466.894584 / -1466.97398 / -1467.5265702 / -1467.598500
ClA•PC2 / 0.300696 / -1466.923017 / -1466.899138 / -1466.978011 / -1467.5300925 / -1467.599545
ClG•RC / 0.305973 / -1542.162274 / -1542.138235 / -1542.218868 / -1542.7982201 / -1542.873072
ClG•TS1 / 0.304395 / -1542.129723 / -1542.104917 / -1542.185281 / -1542.7654496 / -1542.843613
ClG•TS2 / 0.303088 / -1542.115696 / -1542.090108 / -1542.17293 / -1542.7532007 / -1542.835695
ClG•PC1 / 0.304934 / -1542.165985 / -1542.140608 / -1542.223534 / -1542.8054833 / -1542.884612
ClG•PC2 / 0.304179 / -1542.162092 / -1542.13627 / -1542.220181 / -1542.8029063 / -1542.882611
WA•RC / 0.326332 / -1082.767075 / -1082.743087 / -1082.823143 / -1083.3848797 / -1083.622261
WA•TS1 / 0.324312 / -1082.714034 / -1082.690056 / -1082.768025 / -1083.3291048 / -1083.581978
WA•TS2 / 0.3244 / -1082.71778 / -1082.693906 / -1082.772453 / -1083.3321369 / -1083.577998
WA•PC1 / 0.326341 / -1082.784098 / -1082.760171 / -1082.838613 / -1083.4037298 / -1083.642195
WA•PC2 / 0.326722 / -1082.785527 / -1082.761765 / -1082.83952 / -1083.4050137 / -1083.645101
WG•RC / 0.33018 / -1158.026568 / -1158.001704 / -1158.082782 / -1158.67487 / -1158.908279
WG•TS1 / 0.329544 / -1157.988284 / -1157.963438 / -1158.042687 / -1158.6362813 / -1158.876084
WG•TS2 / 0.328315 / -1157.982961 / -1157.95758 / -1158.039447 / -1158.6324669 / -1158.876627
WG•PC1 / 0.331148 / -1158.04292 / -1158.017848 / -1158.098465 / -1158.6962557 / -1158.92634
WG•PC2 / 0.330833 / -1158.048304 / -1158.023092 / -1158.104101 / -1158.701523 / -1158.933462

aCalculated values at the B3LYP/(LanL2DZ+6-31G(d,p)) level. bSingle-point energies at the B3LYP/(LanL2DZ+6-311++G(2d,2p)) level. cEnergies in the aqueous phase at the B3LYP/(LanL2DZ+6-311++G(2d,2p)) level. The suffix g and aq means gas phase and aqua phase respectively. All energy values in a.u..

Table S6 Energy components of the second substitution of Pt-G with adenine (A) or guanine (G) for trans-Pt monoadduct®trans DNA-Pt-DNA diadduct for the title complexes

state / ZPEa / E a / Ha / Ga / Egb / Gaqc
trans-[PtCl2NH3(pyridine)]
GG•RC / 0.396878 / -1584.807968 / -1584.807023 / -1584.901903 / -1585.677796 / -1585.898423
GG•HH•TS / 0.396129 / -1584.773910 / -1584.772966 / -1584.864670 / -1585.642402 / -1585.869678
GG•HH•PC / 0.395800 / -1584.810544 / -1584.809600 / -1584.904250 / -1585.684802 / -1585.911873
GG•HT•TS / 0.395891 / -1584.775461 / -1584.774516 / -1584.865925 / -1585.643334 / -1585.871482
GG•HT•PC / 0.396703 / -1584.817835 / -1584.816891 / -1584.909402 / -1585.692000 / -1585.915687
GA•RC / 0.391336 / -1509.550595 / -1509.549650 / -1509.639383 / -1510.385328 / -1510.609633
GA•HH•TS / 0.391039 / -1509.507659 / -1509.506715 / -1509.596856 / -1510.341822 / -1510.576133
GA•HH•PC / 0.392146 / -1509.559379 / -1509.558435 / -1509.648355 / -1510.399483 / -1510.629092
GA•HT•TS / 0.391034 / -1509.508530 / -1509.507586 / -1509.597888 / -1510.342335 / -1510.576121
GA•HT•PC / 0.391672 / -1509.553542 / -1509.552598 / -1509.646020 / -1510.394542 / -1510.623378
GG•RC / 0.447739 / -1776.486553 / -1776.485609 / -1776.589622 / -1777.460808 / -1777.662790
GG•HH•TS / 0.446887 / -1776.452058 / -1776.451114 / -1776.551977 / -1777.423925 / -1777.633741
GG•HH•PC / 0.447779 / -1776.482336 / -1776.481392 / -1776.583103 / -1777.459689 / -1777.674761
GG•HT•TS / 0.446464 / -1776.455344 / -1776.454400 / -1776.555636 / -1777.427546 / -1777.637922
GG•HT•PC / 0.447139 / -1776.495573 / -1776.494629 / -1776.597329 / -1777.473740 / -1777.678496
GA•RC / 0.443342 / -1701.229328 / -1701.228384 / -1701.329917 / -1702.170332 / -1702.379052
GA•HH•TS / 0.443120 / -1701.189698 / -1701.188754 / -1701.286074 / -1702.126236 / -1702.339176
GA•HH•PC / 0.443755 / -1701.234000 / -1701.233056 / -1701.331037 / -1702.177470 / -1702.392010
GA•HT•TS / 0.442935 / -1701.192011 / -1701.191067 / -1701.287934 / -1702.128823 / -1702.342159
GA•HT•PC / 0.443164 / -1701.229682 / -1701.228738 / -1701.328462 / -1702.173649 / -1702.382918

aCalculated values at the B3LYP/(LanL2DZ+6-31G(d,p)) level. bSingle-point energies at the B3LYP/(LanL2DZ+6-311++G(2d,2p)) level. cEnergies in the aqueous phase at the B3LYP/(LanL2DZ+6-311++G(2d,2p)) level. The suffix g and aq means gas phase and aqua phase respectively. All energy values in a.u..

Table S7 Energy components of the second substitution of Pt-G with adenine (A) or guanine (G) for trans-Pt monoadduct®trans DNA-Pt-DNA diadduct for the title complexes

state / ZPEa / E a / Ha / Ga / Egb / Gaqc
GG•RC / 0.424798 / -1624.140896 / -1624.109085 / -1624.205628 / -1625.0174687 / -1625.228588
GG•HH•TS / 0.423122 / -1624.097499 / -1624.065766 / -1624.160704 / -1624.9749057 / -1625.198665
GG•HH•PC / 0.423981 / -1624.135242 / -1624.102815 / -1624.198564 / -1625.0140108 / -1625.237708
GG•HT•TS / 0.423453 / -1624.102662 / -1624.070924 / -1624.165391 / -1624.979333 / -1625.19971
GG•HT•PC / 0.42419 / -1624.14195 / -1624.109334 / -1624.20527 / -1625.0230137 / -1625.244383
GA•RC / 0.418019 / -1548.873835 / -1548.843409 / -1548.936844 / -1549.7160242 / -1549.940665
GA•HH•TS / 0.418829 / -1548.824925 / -1548.794449 / -1548.886755 / -1549.6681324 / -1549.89792
GA•HH•PC / 0.419177 / -1548.882105 / -1548.850757 / -1548.945107 / -1549.7304352 / -1549.953204
GA•HT•TS / 0.419409 / -1548.837856 / -1548.807582 / -1548.898471 / -1549.680753 / -1549.907609
GA•HT•PC / 0.420456 / -1548.872951 / -1548.842055 / -1548.934318 / 1549.7219008 / -1549.948705
GG•RC / 0.424774 / -1624.14168 / -1624.109725 / -1624.207429 / -1625.018603 / -1625.230142
GG•HH•TS / 0.42317 / -1624.101753 / -1624.069794 / -1624.165837 / -1624.9791833 / -1625.198449
GG•HH•PC / 0.423658 / -1624.137585 / -1624.104876 / -1624.202414 / -1625.016821 / -1625.236667
GG•HT•TS / 0.423315 / -1624.105553 / -1624.073569 / -1624.16932 / -1624.9821605 / -1625.200071
GG•HT•PC / 0.424246 / -1624.143638 / -1624.110878 / -1624.207528 / -1625.0252067 / -1625.240316
GA•RC / 0.417773 / -1548.87543 / -1548.844753 / -1548.939862 / -1549.7176518 / -1549.942982
GA•HH•TS / 0.418573 / -1548.832675 / -1548.801833 / -1548.896156 / -1549.6763799 / -1549.899910
GA•HH•PC / 0.419605 / -1548.884536 / -1548.853261 / -1548.947286 / -1549.7334577 / -1549.954596
GA•HT•TS / 0.418700 / -1548.838995 / -1548.808267 / -1548.901463 / -1549.6818326 / -1549.904794
GA•HT•PC / 0.41942 / -1548.878729 / -1548.847181 / -1548.943303 / -1549.7274705 / -1549.948388
GG•RC / 0.422363 / -1624.14037 / -1624.107954 / -1624.207883 / -1625.0173993 / -1625.236493
GG•HH•TS / 0.423607 / -1624.10461 / -1624.072653 / -1624.169168 / -1624.9810058 / -1625.201964
GG•HH•PC / 0.422844 / -1624.139285 / -1624.106818 / -1624.204118 / -1625.0193986 / -1625.239336
GG•HT•TS / 0.423075 / -1624.107626 / -1624.075553 / -1624.171721 / -1624.984175 / -1625.202678
GG•HT•PC / 0.423748 / -1624.14616 / -1624.113168 / -1624.211859 / -1625.0274544 / -1625.242910
GA•RC / 0.420069 / -1548.881446 / -1548.850765 / -1548.946047 / -1549.7264576 / -1549.944045
GA•HH•TS / 0.418578 / -1548.831854 / -1548.800825 / -1548.89594 / -1549.6750682 / -1549.897757
GA•HH•PC / 0.419701 / -1548.886907 / -1548.85564 / -1548.950951 / -1549.7349638 / -1549.956703
GA•HT•TS / 0.418394 / -1548.835887 / -1548.804811 / -1548.900242 / -1549.6787613 / -1549.901951
GA•HT•PC / 0.419327 / -1548.881276 / -1548.849671 / -1548.945659 / -1549.7301724 / -1549.950774

aCalculated values at the B3LYP/(LanL2DZ+6-31G(d,p)) level. bSingle-point energies at the B3LYP/(LanL2DZ+6-311++G(2d,2p)) level. cEnergies in the aqueous phase at the B3LYP/(LanL2DZ+6-311++G(2d,2p)) level. The suffix g and aq means gas phase and aqua phase respectively. All energy values in a.u..