Synthesis, characterization and biological evaluation of dipicolylamine sulfonamide derivatized platinum complexes as potential anticancer agents

Abstract

Three new Pt complexes, [PtCl2(N(SO2(2-nap))dpa)], [PtCl2(N(SO2(1-nap))dpa)] and [PtCl2(N(SO2pip)dpa)], containing a rare 8-membered ring were synthesized in good yield and high purity by utilizing ligands which contain a dipicolylamine moiety.

Biological Evaluation of Platinum(II) Sulfonamido Complexes: Synthesis, Characterization, Cytotoxicity, and Biological Imaging

“…In general, computed structures are in agreement with the X-ray structures ( Figure 2 ). The S1-N2 bond length in the un-coordinated ligands is ∼1.62 Å ( Table 2 ) and is comparable with the reported values in related compounds in previous studies [ 41 , 42 ]. Furthermore, the S1-N2 bond length in the ligand is not significantly different from that of the platinum complex as the ligand serves as a bidentate ligand, unlike in the case of Re(CO) 3 complexes having similar ligands [ 42 ] Due to the conjugation of lone pair in sulfonamide nitrogen with S=O across the S–N bond, noncoordinated or weakly coordinated sulfonamide groups show significant double bond character [ 43 ].…”

“…The S–N absorption peak of PtCl 2 ( N (SO 2 azobenz)dpa) has shifted toward a lower frequency in comparison with that of the ligand spectrum. In a previous study where Pt is bound to dpa-sulfonamide moiety, we observed a slight shift toward lower frequency for the S–N bond upon binding to Pt [ 42 ].…”

Synthesis and Characterization of Novel Diethylenetriamine Based Sulfonamide Ligands and Their Bidentate Platinum(II) Complexes Toward Anticancer Drug Leads

“…Human non-small lung cancer cell line (NCI-H292) and human normal lung fibroblast cell line (MRC-5) were maintained in Dulbecco's Modified Eagle Medium (DMEM; Sigma Aldrich D5648) supplemented with 10% Fetal Bovine Serum (FBS) and 1% v/v penicillin-streptomycin. All the cells were maintained at 37° C in the incubator having humidified atmosphere with 5% CO2 (Darshani et al, 2020b, Maladeniya et al, 2022, Thushara et al, 2021.…”

Dipicolylamine-Based Fluorescent Probes and Their Potential for the Quantification of Fe3+ in Aqueous Solutions

“…Since DPA is a symmetric secondary amine that has good reactivity, it can be derivatized easily into various ligand systems with different properties. 22 Here, two sulfonamide derivatives of dipicolylamine ligands with two different R groups, N(SO 2 )(R 1 )dpa (L1) and N(SO 2 )(R 2 )dpa (L2), ( Figure 1 ), where R 1 = biphenyl and R 2 = azobenzyl, were developed into fluorophores that can detect Fe 3+ ions with high sensitivity and selectivity. The L1 ligand was designed by combining the sulfonyl chloride containing biphenyl as the R group with the hydrophobic dipicolylamine and characterization was carried out.…”

“…In this study, we have developed two dipicolylamine (DPA)-based ligands into Fe 3+ fluorosensors. Since DPA is a symmetric secondary amine that has good reactivity, it can be derivatized easily into various ligand systems with different properties . Here, two sulfonamide derivatives of dipicolylamine ligands with two different R groups, N­(SO 2 )­(R 1 )­dpa (L1) and N­(SO 2 )­(R 2 )­dpa (L2), (Figure ), where R 1 = biphenyl and R 2 = azobenzyl, were developed into fluorophores that can detect Fe 3+ ions with high sensitivity and selectivity.…”