Synthesis, characterization and in vitro cytotoxic activity of bis(triorganotin) 2,6-pyridinedicarboxylates

Abstract

Two bis(triorganotin) 2,6-pyridinedicarboxylates, 2,6-C 5 H 3 N(COOSnR 3 ) 2 (R = C 6 H 11 -c, 1; C 6 H 5 C(CH 3 ) 2 CH 2 , 2), have been synthesized by the reaction of 2,6-pyridinedicarboxylic acid with triorganotin hydroxide in toluene-ethanol and characterized by means of elemental analysis, FT-IR, 1 H NMR spectroscopy, and single crystal X-ray diffraction analysis. In the compounds, a 2,6-pyridinedicarboxylate dianion binds two triorganotin units in a monodentate manner and both tin atoms exist in a distorted tetrahedral environment. Bioassay results have shown that the compounds possess good in vitro cytotoxic activity against two human tumor cell lines, Hela and MCF-7.

Synthesis, structure and in vitro cytotoxic activity of two organotin complexes of 2-phenyl-1,2, 3-triazole-4-carboxylic acid

“…The activity of 1 is comparable with that of other di-n-butylstannoxanes such as {[n-Bu 2 (3-FC 6 H 4 COO) Sn] 2 O} 2 (MCF-7, IC 50 0.496 μg/mL) and {[n-Bu 2 (2-HO-4-MeOC 6 H 3 COO)Sn] 2 O} 2 (MCF-7, IC 50 0.131 μg/mL) (Gielen, 2002), but better than that of {[n-Bu 2 (2-O 2 NC 6 H 4 CH = CHOO) Sn] 2 O} 2 (HeLa, IC 50 5.717 μg/mL) (Liu et al, 2011). The activity of 2 is similar to that of our previously reported tricyclohexyltin 2-phenyl-1,2,3-triazole-4-carboxylate (Tian et al, 2005) bis(triorganotin) 2,6-pyridinedicarboxylates (Wang et al, 2014), but is lower than triphenyltin 2-phenyl-1,2, 3-triazole-4-carboxylate (Tian et al, 2005). Gielen et al found that the di-and triorganotin steroid carboxylates, crown-ethercarboxylates and fluorine-substituted carboxylates exhibited quite potent cytotoxicities against many human tumor cell lines such as MCF-7, EVSAT, WiDr, IGROV, MI9, A498 and H226 (Gielen, 2002;Gielen et al, 2005).…”

“…Many researchers have described the preparation and characterization of organotin carboxylates and their activity against tumors, fungi, bacteria and other microorganisms (Shang et al, 2011;Seter et al, 2012;Kaur et al, 2013;Nath et al, 2013Nath et al, , 2014Dong et al, 2014;Wang et al, 2014;Mao et al, 2015). It has been observed that some di-and triorganotin carboxylates show potential as antineoplastic agents (Hadjikakou and Hadjiliadis, 2009;Amir et al, 2014;Carraher and Roner, 2014).…”

Syntheses and crystal structures of three bis(triorganotin) benzenedicarboxylates

“…The tetrahedral nature of tris(2-methyl-2-phenylpropyl)tin carboxylates arises from the crowding of the three organic groups covalently bonded to the tin atom, and such compounds are an exception to the observation that trialkyltin carboxylates auto-associate into polymers through carboxylate bridging (Tiekink, 1994;Chandrasekhar et al, 2002). The four bond lengths to Sn (Table 1) are similar to those found in other reported tris(2-methyl-2-phenylpropyl)tin carboxylates, such as 3,5-di-tert-butyl-4-hydroxybenzoate (Ding et al, 2012), and 2,6-pyridinedicarboxylate (Wang et al, 2014) The monodentate mode of coordination of the carboxylate group is also reflected in the two disparate C-O bond lengths (C(7)-O(1) of 1.289(4) Å and C(7)-O(2) of 1.222(4) Å, and C(8)-O(3) of 1.297(4) Å and C(8)-O(4) of 1.216(4) Å). The carboxylate groups and phenyl ring from the 1,3-benzenedicarboxylate ligand are not in the same plane, and the dihedral angles between the phenyl ring and each of the two carboxylate planes are 9.80(1)° and 19.82(1)°, respectively, and the dihedral angle between the two carboxylate planes is 14.43(2)°.…”

Synthesis, crystal structure and cytotoxic activity of tricyclohexyltin complexes of benzenedioxyacetic acids

“…In recent years, organotin carboxylates have been receiving considerable attention due to their structural interest and various applications . Many workers have described the preparation and characterization of organotin carboxylates and their activity against tumors, fungi, bacteria and other microorganisms . It has been observed that some di‐ and triorganotin carboxylates show potential as antineoplastic agents .…”