Naphthalene appended diethylenetriamine based ligands and their platinum complexes as cancer theranostic agents

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Date

2024

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Faculty of Science, University of Kelaniya Sri Lanka

Abstract

Dual action compounds with both diagnostic and therapeutic properties are extremely beneficial in treating cancers. Naphthalene sulfonamides are known fluorescent species due to the conjugated aromatic systems and they show sigma receptor targeting potential when bonded to diethylenetriamine. Here we present two new naphthalene sulfonamide ligands N(SO2-1-naphthalene) dien (L1) and N(SO2- 2-naphthalene)dien (L2) with their platinum complexes [Pt(N(SO2-1-naphthalene)dien)Cl]Cl (C1) and [Pt(N(SO2-2-naphthalene)dien)Cl]Cl (C2). The ligands L1 and L2 were synthesized by derivatizing the central N atom of diethylenetriamine, unlike the conventional ligands reported by derivatizing the terminal N atom of diethylenetriamine. All the compounds were synthesized in good yields and characterized using spectroscopic methods; UV-Visible, FTIR and 1H NMR spectroscopy. UV-Visible spectra of all compounds show absorption peaks due to n→π* electronic transitions in the region of 225-235 nm and absorption peaks corresponding to π→π* transitions were observed within the region of 265-300 nm. FTIR spectra aided to identify special functional group vibrations such as S-N bond vibrations and 1H NMR spectra were used in elucidating the structures of synthesized ligands and complexes. All of these species bear highly conjugated fluorophores (1-naphthalene and 2-naphthalene) which empower them as potential fluorescent imaging agents in diagnosis of cancer. By using Swiss TargetPrediction server, the biological targets for these two ligands were identified and sigma opioid receptor (SIGMAR-1) showed the highest probability showing their potential to act as cancer therapeutic drug leads. Moreover, both ligands obey the Lipinski rules ensuring their drug likeness. The structures of the ligands were geometrically optimized using the Gaussian 16 programme package, B3LYP/6-31G(d) level of theory. Theoretical molecular docking studies were performed to calculate binding affinities of ligands to the protein SIGMAR-1 (PDB ID: 5HK2) by AutoDock Vina wizard in PyRx 0.9.4 software, resulting -6.4 kcal/mol and -5.5 kcal/mol binding affinities for L1 and L2, respectively. Equipped with both therapeutic and diagnostic properties these compounds may serve as potential theranostic agents in the battle against cancer.

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Keywords

Cancer, Diethylenetraiamine, Naphthalene, Platinum, Sigma receptor

Citation

Edirisinghe L. G.; Perera I. C.; Perera N. T. (2024), Naphthalene appended diethylenetriamine based ligands and their platinum complexes as cancer theranostic agents, Proceedings of the International Conference on Applied and Pure Sciences (ICAPS 2024-Kelaniya) Volume 4, Faculty of Science, University of Kelaniya Sri Lanka. Page 88

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