Vibrational frequencies and intramolecular force constants for cisplatin: assessing the role of the platinum basis set and relativistic effects

Almeida, Caroline A. de; Pinto, Larissa P.N.M.; Santos, Hélio F. Dos; Paschoal, Diego

doi:10.1007/s00894-021-04937-4

Cited by 8 publications

(7 citation statements)

References 59 publications

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“…The B3LYP hybrid functional , has been used along with the RIJK approximation . The Sapporo-DKH3-DZP-2012 basis set has been used for gold transition metal, DKH-def2-TZVP(-f) was used for Cl, IGLO-II was used for C, and DKH-def2-SVP was used for the rest of the atoms (O, N, and H). , The same method is also employed for 13 C NMR calculations in the case of TMS.…”

Section: Resultsmentioning

confidence: 99%

“…Two types of software have been used for visualization of optimized geometry, namely, Chemcraft 1.6 81 and Gaussview 6.0. 82 Natural bonding analysis (NBO) 69 and Wiberg bond index (WBI) 70 analysis also has been done in Gaussian 09 software by performing DFT methods. NBO analysis explains the details of the bonding orbitals present in the bond and also provides the natural charges ( Figures S206–S212 and Table S40 ).…”

Section: Methodsmentioning

confidence: 99%

“… 69 This RI approximation has been found to be fast for small to medium molecules. The basis set combination used for 13 C NMR is Sapporo-DKH3-DZP-2012 for gold(I) metal, 70 DKH-def2-TZVP(−f) for the Cl atom, 83 and IGLO-II for the carbon atom, 71 and for the rest of the atoms, Si, O, N, and H, the DKH-def2-SVP 64 , 72 basis set has been taken into account. Optimized coordinates of Gaussian 09 software have been used for the 13 C NMR calculations.…”

Section: Methodsmentioning

confidence: 99%

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Accessing Bioactive Hydrazones by the Hydrohydrazination of Terminal Alkynes Catalyzed by Gold(I) Acyclic Aminooxy Carbene Complexes and Their Gold(I) Arylthiolato and Gold(III) Tribromo Derivatives: A Combined Experimental and Computational Study

et al. 2023

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Hydrohydrazination of terminal alkynes with hydrazides yielding hydrazones 5–14 were successfully catalyzed by a series of gold(I) acyclic aminooxy carbene complexes of the type [{(4-R2-2,6-t-Bu2-C6H2O)(N(R1)2)}methylidene]AuCl, where R2 = H, R1 = Me (1b); R2 = H, R1 = Cy (2b); R2 = t-Bu, R1 = Me (3b); R2 = t-Bu, R1 = Cy (4b). The mass spectrometric evidence corroborated the existence of the catalytically active solvent-coordinated [(AAOC)Au(CH3CN)]SbF6 (1–4)A species and the acetylene-bound [(AAOC)Au(HCCPhMe)]SbF6 (3B) species of the proposed catalysis cycle. The hydrohydrazination reaction was successfully employed in synthesizing several bioactive hydrazone compounds (15–18) with anticonvulsant properties using a representative precatalyst (2b). The DFT studies favored the 4-ethynyltoluene (HCCPhMe) coordination pathway over the p-toluenesulfonyl hydrazide (NH2NHSO2C6H4CH3) coordination pathway, and that proceeded by a crucial intermolecular hydrazide-assisted proton transfer step. The gold(I) complexes (1–4)b were synthesized from the {[(4-R2-2,6-t-Bu2-C6H2O)(N(R1)2)]CH}+OTf– (1–4)a by treatment with (Me2S)AuCl in the presence of NaH as a base. The reactivity studies of (1–4)b yielded the gold(III) [{(4-R2-2,6-t-Bu2-C6H2O)(N(R1)2)}methylidene]AuBr3 (1–4)c complexes upon reaction with molecular bromine and the gold(I) perfluorophenylthiolato derivatives, [{(4-R2-2,6-t-Bu2-C6H2O)(N(R1)2)}methylidene]AuSC6F5 (1–4)d, upon treatment with C6F5SH.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Accessing Bioactive Hydrazones by the Hydrohydrazination of Terminal Alkynes Catalyzed by Gold(I) Acyclic Aminooxy Carbene Complexes and Their Gold(I) Arylthiolato and Gold(III) Tribromo Derivatives: A Combined Experimental and Computational Study

et al. 2023

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“…Cyclo-HH and all drugs except CIS were parametrized using CGENFF , (program version 2.5, compatible with the CGenFF version 4.6; accessed on October 2022). CIS was parametrized in accordance with the topologies of quantum dynamics performed in water solvent by Yesylevskyy et al, which was also previously used in other studies. − …”

Section: Methodsmentioning

confidence: 99%

Co-Assembly of Cancer Drugs with Cyclo-HH Peptides: Insights from Simulations and Experiments

Vlachou,

Kumar,

Tiwari

et al. 2024

ACS Appl. Bio Mater.

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Peptide-based nanomaterials can serve as promising drug delivery agents, facilitating the release of active pharmaceutical ingredients while reducing the risk of adverse reactions. We previously demonstrated that Cyclo-Histidine-Histidine (Cyclo-HH), co-assembled with cancer drug Epirubicin, zinc, and nitrate ions, can constitute an attractive drug delivery system, combining drug self-encapsulation, enhanced fluorescence, and the ability to transport the drug into cells. Here, we investigated both computationally and experimentally whether Cyclo-HH could co-assemble, in the presence of zinc and nitrate ions, with other cancer drugs with different physicochemical properties. Our studies indicated that Methotrexate, in addition to Epirubicin and its epimer Doxorubicin, and to a lesser extent Mitomycin-C and 5-Fluorouracil, have the capacity to co-assemble with Cyclo-HH, zinc, and nitrate ions, while a significantly lower propensity was observed for Cisplatin. Epirubicin, Doxorubicin, and Methorexate showed improved drug encapsulation and drug release properties, compared to Mitomycin-C and 5-Fluorouracil. We demonstrated the biocompatibility of the co-assembled systems, as well as their ability to intracellularly release the drugs, particularly for Epirubicin, Doxorubicin, and Methorexate. Zinc and nitrate were shown to be important in the co-assembly, coordinating with drugs and/or Cyclo-HH, thereby enabling drug-peptide as well as drug−drug interactions in successfully formed nanocarriers. The insights could be used in the future design of advanced cancer therapeutic systems with improved properties.

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“…[10][11][12] Several search groups have successfully used the above mentioned basis set (see, e.g., Refs. [13][14][15][16][17][18][19][20][21]).…”

Section: Introductionmentioning

confidence: 99%

All-electron ZORA triple zeta basis sets for the elements Cs–La and Hf–Rn

Neto

Jorge²,

Cruz³

2023

Chinese Phys. B

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Segmented all-electron basis set of triple zeta valence quality plus polarization functions (TZP) for the elements of the fifth row to be used together with the zero-order regular approximation (ZORA) was carefully constructed. To correctly describe electrons distant from atomic nuclei, the basis set was augmented with diffuse functions giving rise to a set designated as ATZP-ZORA. At the ZORA-B3LYP theory level, these sets were used to calculate ionization energies and mean dipole polarizabilities of some atoms and bond lengths, dissociation energies, and harmonic vibrational frequencies of diatomic molecules. Then, these results were compared with theoretical and experimental data found in the literature. Even considering that our sets are relatively compact, they are sufficiently accurate and reliable to perform property calculations involving simultaneously electrons from the inner and outer shells. An evaluation of the performances of the ZORA and second-order Douglas-Kroll-Hess Hamiltonians was carried out and the results are here discussed.

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Vibrational frequencies and intramolecular force constants for cisplatin: assessing the role of the platinum basis set and relativistic effects

Cited by 8 publications

References 59 publications

Accessing Bioactive Hydrazones by the Hydrohydrazination of Terminal Alkynes Catalyzed by Gold(I) Acyclic Aminooxy Carbene Complexes and Their Gold(I) Arylthiolato and Gold(III) Tribromo Derivatives: A Combined Experimental and Computational Study

Accessing Bioactive Hydrazones by the Hydrohydrazination of Terminal Alkynes Catalyzed by Gold(I) Acyclic Aminooxy Carbene Complexes and Their Gold(I) Arylthiolato and Gold(III) Tribromo Derivatives: A Combined Experimental and Computational Study

Co-Assembly of Cancer Drugs with Cyclo-HH Peptides: Insights from Simulations and Experiments

All-electron ZORA triple zeta basis sets for the elements Cs–La and Hf–Rn

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