On the bioreactivity of triorganotin aminobenzoates. Investigation of trialkyl and triarylyltin(IV) esters of 3-amino and 4-aminobenzoic acids

Tzimopoulos, Demetrios I.; Sanidas, Ioannis; Varvogli, Anastasia.-C.; Czapik, Agnieszka; Gdaniec, Мaria; Nikolakaki, Eleni; Akrivos, Pericles D.

doi:10.1016/j.jinorgbio.2009.12.006

Cited by 42 publications

(29 citation statements)

References 44 publications

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“…Tin complexes have witnessed vast range of applications in various biological and industrial fields . Such compounds possess fascinating medicinal importance like antiparasite agents, in horticulture as bactericidal, acraricidal and fungicidal medium, anti‐HIV and antitumor agents . The biological activity and specially the anticancer activity of tin compounds is governed by geometrical features, extent of hydrolysis of ligands and coordination number around central tin metal ion .…”

Section: Introductionmentioning

confidence: 92%

Unprecedented isolation of a dinuclear tin (II) complex stabilized by pyridine‐2,6‐dimethanol: structure, DFT and in vitro screening of cytotoxic properties

Mantasha

Raza

Shahid

et al. 2019

Applied Organom Chemis

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In this work, we report a novel dinuclear Sn (II) complex, [Sn 2 (Hpdm) 2 (H 2 O) 6 ] 2H 2 O 2Cl (1) (H 2 pdm = pyridine-2,6-dimethanol), which has been crystallized out and characterized by elemental analysis, FTIR, 1 H and 13 C NMR, single crystal X-ray studies and Density Functional Theory (DFT) analysis. X-ray structure of 1 has confirmed it to be a dinuclear alkoxo-bridged Sn (II) species where each metal adopts a seven coordinate distorted pentagonal bipyramidal (pbp) geometry. This is the first hepta-coordinated Sn (II) complex ever isolated apart from already reported stannylenes. Spin density plots from DFT support the +2 oxidation state of each tin metal. Hirshfeld surface analysis reveals the presence of various H-bonding interactions in the molecule and molecular docking results along with DFT confirm higher binding affinity of the present complex towards DNA. Moreover, the complex exhibits promising anticancer activities against HeLa and A549 cancer cell lines.

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Section: Introductionmentioning

confidence: 92%

Unprecedented isolation of a dinuclear tin (II) complex stabilized by pyridine‐2,6‐dimethanol: structure, DFT and in vitro screening of cytotoxic properties

Mantasha

Raza

Shahid

et al. 2019

Applied Organom Chemis

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“…The results from an investigation into the trialkyl and triarylyltin(IV) esters of 3-aminobenzoic acids (36-38) and 4-aminobenzoic acids (39-41) revealed that complexes with more lipophilic organic groups, such as butyl and phenyl derivatives, exhibited significant cytotoxic activity on HeLa, K562, and HepG2 cells, with butyl derivatives exerting a more dramatic effect. [46] Trin-butyltin (42) and triphenyltin (43) derivatives of indomethacin were more active than cisplatin against cervical cancer cells (HeLa cells) and human lung cancer cells (SKLU-1 cells). [47] In a study involving organotin(IV) carboxylates of lauric acid (44 and 45), the authors concluded that these complexes were more potent than diorganotin(IV) analogs because of the availability of their coordination positions around the tin atom.…”

Section: Triorganotin Carboxylatesmentioning

confidence: 99%

“…The September 2014 release of the cancer screening data from the NCI reported over 350 organotin complexes with potential anticancer activity. [2] Generally, the tin (Sn) atom of organotin complexes with the formula RSnL covalently binds to one (or more) organic alkyl or aryl group, R, or ligand, L. An organotin Table 2 [ 17,18,20,26] 3 [19,21,26,27] 4 - [19,20] 5 - [19,20] 6 - [19] 8 - [20,28] 9 - [20] 10 - [29,30] 11 - [30] 12 >1,000 -- [32] 17 >1,000 -- [33] 19 - [41,42] 27 - [41,42] 29 - [44] 34 - [44] 35 >1,000 -- [46] 37 >1,000 -- [46] 40 42 [a] Figure 2…”

Section: Introductionmentioning

confidence: 99%

Triorganotin complexes in cancer chemotherapy: Mechanistic insights and future perspectives

Anasamy

Chee

Wong

et al. 2020

Applied Organom Chemis

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Current anticancer drug discovery and development efforts are aimed at identifying new complexes that can potently and selectively target DNA and modulate the functions of target proteins. Tin complexes, categorized as monoorganotin (RSnL3), diorganotin (R2SnL2), triorganotin (R3SnL), or tetraorganotin (R4SnL), are one of the most studied complexes in the metal‐based anticancer drug discovery and development field. Among these, diorganotins and triorganotins are widely reported to possess promising anticancer properties, with triorganotins offering several potential advantages over diorganotins, such as a higher total surface area causing higher lipophilicity and hence higher cytotoxicity in cancer cells. However, information on triorganotins' direct therapeutic targets, an in‐depth understanding of their mechanism of action, and useful therapeutic strategies are still lacking. In this review, we discuss the results from in vitro and in vivo mechanistic studies of triorganotin complexes as reported in recent years (2007–2019) and elaborate on the underlying mechanisms that could aid in the identification of triorganotin complex molecular targets. We conclude by identifying present obstacles faced by triorganotin complexes that avert their translation to the clinical phase and current strategies employed to overcome the aforementioned obstacles, and we offer considerations for their future development. These findings are anticipated to stimulate further developments of novel and innovative triorganotin complexes as anticancer drug candidates.

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“…Recent studies have shown very promising in vitro antitumor properties of organotin(IV) compounds, against a wide panel of tumor cell lines of human origin [17][18][19][20][21]. e organotin(IV) complexes with carboxylate [22][23][24][25][26][27][28][29], thiolato [30][31][32][33][34][35][36], and dithiocarbamato [37] ligands have been extensively studied, and it was found that (carboxylato)triphenyltin(IV) and tetraorganotin(IV) compounds show the highest cytotoxic activity [22,38]. However, the possible application of the synthesized organotin(IV) derivatives was very limited due to their poor water solubility [39].…”

Section: Introductionmentioning

confidence: 99%

Design and In Vitro Biological Evaluation of a Novel Organotin(IV) Complex with 1-(4-Carboxyphenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione

Pantelić

Zmejkovski

Žižak

et al. 2019

Journal of Chemistry

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A novel triphenyltin(IV) compound with 1-(4-carboxyphenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione was synthesized and characterized by IR, NMR spectroscopy, mass spectrometry, and elemental analysis. In vitro anticancer activity of ligand precursor and synthesized organotin(IV) compound was determined against tumor cell lines: human adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human breast cancer (MDA-MB-453), using microculture tetrazolium test (MTT) assay. The results indicate that complex exhibited very high antiproliferative activity against all tested cell lines with IC50 values in the range of 0.22 to 0.53 µM. The highest activity organotin(IV) compound expressed against the HeLa cells (IC50 = 0.22 ± 0.04 µM). The ligand precursor did not show anticancer activity (IC50 > 200 µM). Furthermore, fluorescence microscopy analysis of HeLa cells reveal that organotin(IV) complex induced apoptosis as a mode of cell death, which is consistent with the increase of cells in the sub-G1 phase.

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On the bioreactivity of triorganotin aminobenzoates. Investigation of trialkyl and triarylyltin(IV) esters of 3-amino and 4-aminobenzoic acids

Cited by 42 publications

References 44 publications

Unprecedented isolation of a dinuclear tin (II) complex stabilized by pyridine‐2,6‐dimethanol: structure, DFT and in vitro screening of cytotoxic properties

Unprecedented isolation of a dinuclear tin (II) complex stabilized by pyridine‐2,6‐dimethanol: structure, DFT and in vitro screening of cytotoxic properties

Triorganotin complexes in cancer chemotherapy: Mechanistic insights and future perspectives

Design and In Vitro Biological Evaluation of a Novel Organotin(IV) Complex with 1-(4-Carboxyphenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione

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