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Molecular basis of the interaction of novel tributyltin(IV) 2/4-[(E)-2-(aryl)-1-diazenyl]benzoates endowed with an improved cytotoxic profile: Synthesis, structure, biological efficacy and QSAR studies

Published on Sep 1, 2010in Journal of Inorganic Biochemistry3.22
· DOI :10.1016/j.jinorgbio.2010.05.001
Tushar S. Basu Baul23
Estimated H-index: 23
(NEHU: North Eastern Hill University),
Anup Paul6
Estimated H-index: 6
(NEHU: North Eastern Hill University)
+ 8 AuthorsUlli Englert33
Estimated H-index: 33
(RWTH Aachen University)
Cite
Abstract
Abstract A series of tributyltin(IV) complexes based on 2/4-[( E )-2-(aryl)-1-diazenyl]benzoate ligands was synthesized, wherein the position of the carboxylate and aryl substituents (methyl, tert -butyl and hydroxyl) varies. The complexes, Bu 3 SnL 1–4 H ( 1 – 4 ), have been structurally characterized by elemental analysis and IR, NMR ( 1 H, 13 C, and 119 Sn) and 119 Sn Mossbauer spectroscopy. All have a tetrahedral geometry in solution and a trigonal bipyramidal geometry in the solid-state, except for Bu 3 SnL 4 H ( 4 ) that was ascertained to have tetrahedral coordination by X-ray crystallography. Cytotoxicity studies were carried out on human tumor cell lines A498 (renal cancer), EVSA-T (mammary cancer), H226 (non-small-cell lung cancer), IGROV (ovarian cancer), M19 MEL (melanoma), MCF-7 (mammary cancer) and WIDR (colon cancer). Compared to cisplatin, test compounds 1 – 4 had remarkably good activity, despite the presence of substantial steric bulk due to Sn–Bu ligands. The quantitative structure–activity relationship (QSAR) studies for the cytotoxicity of organotin(IV) benzoates, along with some reference drug molecules, is also discussed against a panel of human tumor cell lines. Molecular structures of the tributyltin(IV) complexes ( 1 – 4 ) were fully optimized using the PM6 semi-empirical method and docking studies performed with key enzymes associated with the propagation of cancer, namely ribonucleotide reductase, thymidylate synthase, thymidylate phosphorylase and topoisomerase II. The theoretical results are discussed in relation to the mechanistic role of the cytotoxic active test compounds ( 1 – 4 ).
  • References (42)
  • Citations (23)
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References42
Newest
Published on Apr 1, 2009in Investigational New Drugs2.66
Angela Alama20
Estimated H-index: 20
,
Maurizio Viale18
Estimated H-index: 18
+ 4 AuthorsFabio Sparatore21
Estimated H-index: 21
(UniGe: University of Genoa)
The cytotoxicity in vitro and antitumor activity in vivo of the organotin compound tri-n-butyltin(IV)lupinylsulfide hydrogen fumarate (IST-FS 35) have been investigated. The IC50 values obtained in a panel of tumor cell lines were compared to those of the parental compound IST-FS 29 in the same cells. IST-FS 35 resulted significantly more active than IST-FS 29 with IC50 values in the range 0.16–1.8 μM. Toxicity studies in vivo, after intravenous administration of escalating concentrations of IST...
Published on Mar 1, 2009in Journal of Biological Inorganic Chemistry3.63
Eva Corral3
Estimated H-index: 3
(LEI: Leiden University),
Anna C. G. Hotze8
Estimated H-index: 8
(University of Birmingham)
+ 4 AuthorsJan Reedijk73
Estimated H-index: 73
(LEI: Leiden University)
Various interaction modes between a group of six ruthenium polypyridyl complexes and DNA have been studied using a number of spectroscopic techniques. Five mononuclear species were selected with formula [Ru(tpy)L1L2](2−n)+, and one closely related dinuclear cation of formula [{Ru(apy)(tpy)}2{μ-H2N(CH2)6NH2}]4+. The ligand tpy is 2,2′:6′,2″-terpyridine and the ligand L1 is a bidentate ligand, namely, apy (2,2′-azobispyridine), 2-phenylazopyridine, or 2-phenylpyridinylmethylene amine. The ligand L...
Published on Jan 1, 2009in Coordination Chemistry Reviews13.48
Sotiris K. Hadjikakou34
Estimated H-index: 34
(UoI: University of Ioannina),
Nick Hadjiliadis36
Estimated H-index: 36
(UoI: University of Ioannina)
Tin compounds and their therapeutic potentials are under consideration from many research groups, while a number of early reviews recording advances in the screening for antiproliferative potential of organotins are also available. This review focuses upon results obtained on the antiproliferative activity of tin compounds in the past 5 years.
Published on Jan 1, 2008in Acta Crystallographica Section A1.88
George M. Sheldrick50
Estimated H-index: 50
(GAU: University of Göttingen)
An account is given of the development of the SHELX system of computer programs from SHELX-76 to the present day. In addition to identifying useful innovations that have come into general use through their implementation in SHELX, a critical analysis is presented of the less-successful features, missed opportunities and desirable improvements for future releases of the software. An attempt is made to understand how a program originally designed for photographic intensity data, punched cards and ...
Published on Oct 20, 2007in Journal of Molecular Modeling1.33
James J. P. Stewart7
Estimated H-index: 7
Several modifications that have been made to the NDDO core-core interaction term and to the method of parameter optimization are described. These changes have resulted in a more complete parameter optimization, called PM6, which has, in turn, allowed 70 elements to be parameterized. The average unsigned error (AUE) between calculated and reference heats of formation for 4,492 species was 8.0 kcal mol−1. For the subset of 1,373 compounds involving only the elements H, C, N, O, F, P, S, Cl, and Br...
Published on Jul 1, 2007in Coordination Chemistry Reviews13.48
Peter J. Barnard19
Estimated H-index: 19
(UWA: University of Western Australia),
Susan J. Berners-Price42
Estimated H-index: 42
(UWA: University of Western Australia)
Abstract There is much recent evidence showing that mitochondria play a critical role in the regulation of apoptosis (programmed cell death), making them an attractive target for the design of new anticancer drugs. A variety of different strategies targeting mitochondria for cancer therapy have been described in recent literature. Several different classes of gold-based compounds (in both Au(I) and Au(III) oxidation states) have attracted interest as potential antitumour agents and there is evid...
Published on Feb 23, 2007
Klaus T. Wanner20
Estimated H-index: 20
,
Georg Höfner16
Estimated H-index: 16
Published on Nov 1, 2006in Applied Organometallic Chemistry3.26
Tushar S. Basu Baul23
Estimated H-index: 23
(NEHU: North Eastern Hill University),
Keisham Surjit Singh7
Estimated H-index: 7
(NEHU: North Eastern Hill University)
+ 4 AuthorsGeorge Eng21
Estimated H-index: 21
(UDC: University of the District of Columbia)
Triorganotin(IV) complexes of 4-[(E)-2-(3-formyl-4-hydroxyphenyl)-1-diazenyl]- and 4-{(E)-4-hydroxy-3-[(E)-4-(aryl)iminomethyl]phenyldiazenyl}-benzoic acids (aryls = 4-CH3, 4-Br, 4-Cl, 4-OCH3) have been synthesized. The structures have been characterized by 1H, 13C, 119Sn NMR, IR and 119mSn Mossbauer spectroscopies. The crystal structures of Ph3Sn[O2CC6H4{NN(C6H3-4-OH[C(H)NC6H4CH3-4])}-p] and nBu3Sn[O2CC6H4{NN(C6H3-4-OH[C(H)NC6H4Br-4])}-p] are also reported. The 119Sn Mossbauer and 119Sn NMR dat...
Published on May 1, 2006in Current Medicinal Chemistry3.89
Adnan S. Abu-Surrah20
Estimated H-index: 20
,
Mika Kettunen10
Estimated H-index: 10
(UCD: University College Dublin)
In the next two decades, the world is expected to see around 20 million cases of cancer. Moreover, the types of cancer will vary considerably from country to other. Therefore, all efforts will be needed to face such a vast diversity of problems. With current annual sales of about $500 millions, the platinum(II) complex known as cisplatin (cis- (NH3)2PtCl2) is still one of the most effective drugs to treat testicular, ovarian, bladder and neck cancers. Since it was launched in 1978 there has been...
Cited By23
Newest
Published on May 6, 2019in Mini-reviews in Medicinal Chemistry2.84
Tehreem Tahir1
Estimated H-index: 1
(IUB: Islamia University),
Muhammad Ashfaq11
Estimated H-index: 11
(IUB: Islamia University)
+ 3 AuthorsAreeba Ashfaq (Bahawal Victoria Hospital)
Published on May 1, 2019in Journal of Inorganic Biochemistry3.22
C.N. Banti16
Estimated H-index: 16
(UoI: University of Ioannina),
Sotiris K. Hadjikakou34
Estimated H-index: 34
(UoI: University of Ioannina)
+ 1 AuthorsNick Hadjiliadis36
Estimated H-index: 36
(UoI: University of Ioannina)
Abstract Organotins(IV) exhibit significant in vitro anti-proliferative activity, while the in vivo tests are encouraging. The recent reports on the anti-proliferative activity of organotin(IV) compounds are summarized in this review. The period covered by this work goes back to 2009 until late 2018, while the earlier ones, are included over the previous review of our group published by S.K. Hadjikakou, N. Hadjiliadis, in Coord Chem Rev, 253 (2009) 235–249. During the last decade (2009–2018), >3...
Published on Sep 1, 2018in Inorganic Chemistry Communications1.79
Ranjana Kumari2
Estimated H-index: 2
(IITR: Indian Institute of Technology Roorkee),
Mala Nath22
Estimated H-index: 22
(IITR: Indian Institute of Technology Roorkee)
Abstract Novel trimethyltin(IV) ( 1 ) and tributyltin(IV) ( 2 ) derivatives of an anticoagulant drug warfarin (WR) have been synthesized and characterized through elemental analysis, FTIR studies, multinuclear NMR and ESI mass spectrometry and DFT calculation. Their DNA binding profile (mode and extent of binding with CT DNA) through UV–visible and fluorescence spectrophotometric titrations reveal their partial intercalation inside the base pairs of DNA, and the binding constant ( K b ) calculat...
Published on Oct 1, 2017in Applied Organometallic Chemistry3.26
George Eng21
Estimated H-index: 21
(UDC: University of the District of Columbia)
The aim of this review is to examine the current status of quantitative structure–activity/property relationships (QSAR/QSPR) as related to organotin chemistry. QSAR/QSPR are mathematical models that relate some measurable biological activity or physical property in a series of similar compounds to a descriptor or descriptors associated with the molecules. Descriptors used in QSAR/QSPR studies are endless, from traditional parameters to newly developed ones. They range from quantum chemical desc...
Published on Sep 1, 2017in Journal of Inorganic Biochemistry3.22
Anup Paul11
Estimated H-index: 11
(IST: Instituto Superior Técnico),
Susanta Hazra22
Estimated H-index: 22
(IST: Instituto Superior Técnico)
+ 3 AuthorsArmando J. L. Pombeiro58
Estimated H-index: 58
(IST: Instituto Superior Técnico)
Abstract Synthesis, inter-conversions and biological study of the dichloro bridged dicopper(II) compound [CuLCl] 2 ( 1 ) and its two mononuclear derivatives [CuLCl(H 2 O)]·H 2 O ( 2 ) and [CuLCl(py)] ( 3 ) (HL = 2-(2-pyridylmethyleneamino)benzenesulfonic acid) are described. The dimeric compound 1 collapses into monomers 2 and 3 in the presence of coordinating solvents, water and pyridine, respectively, and 1 is regenerated upon simple stirring of 2 or 3 in methanol. The reactions of 1 with neut...
Published on May 1, 2017in Scientific Reports4.01
Rais Ahmad Khan14
Estimated H-index: 14
,
Mohammad Usman5
Estimated H-index: 5
+ 9 AuthorsFabio Marchetti33
Estimated H-index: 33
Heteroleptic Copper(I) Complexes of “Scorpionate” Bis-pyrazolyl Carboxylate Ligand with Auxiliary Phosphine as Potential Anticancer Agents: An Insight into Cytotoxic Mode
Published on Jan 1, 2017in New Journal of Chemistry3.07
Ya-Ru Qiu1
Estimated H-index: 1
(Liaocheng University),
Rufen Zhang19
Estimated H-index: 19
(Liaocheng University)
+ 3 AuthorsChunlin Ma14
Estimated H-index: 14
(Liaocheng University)
A cluster of novel organotin(IV) complexes with the formulas [Me3Sn(O2CCH2SeC6H4F-p)]n (1), [(Me2Sn)4(μ3-O)2(O2CCH2SeC6H4F-p)4] (2), [n-Bu3Sn(O2CCH2SeC6H4F-p)]n (3) and [n-Bu2Sn(O2CCH2SeC6H4F-p)2] (4) were designed, synthesized, and characterized by elemental analysis, FT-IR, and NMR (1H, 13C, and 119Sn) spectroscopy as well as single-crystal X-ray diffraction. Complexes 1 and 3 represent one-dimensional (1D) coordination polymers composed of alternate [Sn–O]2. The molecular spatial structure of...
Published on Jan 1, 2017in New Journal of Chemistry3.07
Leila Tabrizi11
Estimated H-index: 11
(IUT: Isfahan University of Technology),
Hossein Chiniforoshan11
Estimated H-index: 11
(IUT: Isfahan University of Technology)
A new class of cyclometalated copper(I) complexes with NCN pincer and N-aryl-1,3,5-triaza-7-phosphaadamantane (PTA-PhR) ligands of formula [Cu(L)(PTA-PhR)](PF6) (R = Me (1), Et (2), iPr (3), and HL = 5-methoxy-1,3-bis(1-methyl-1H-benzo[d]imidazol-2-yl)benzene) have been synthesized by C–H activation and fully characterized. The cytotoxicity of the complexes was evaluated against a panel of several human tumor cell lines. All the complexes showed in vitro antitumor activity comparable to that of ...
Published on Sep 1, 2016in Journal of Inorganic Biochemistry3.22
Susanta Hazra22
Estimated H-index: 22
(IST: Instituto Superior Técnico),
Anup Paul11
Estimated H-index: 11
(IST: Instituto Superior Técnico)
+ 3 AuthorsArmando J. L. Pombeiro58
Estimated H-index: 58
(IST: Instituto Superior Técnico)
Abstract Syntheses, crystal structures and biological activities of the diphenoxo-bridged diorgano dinuclear Sn(IV) compounds [Sn(Et) 2 (HL)(H 2 O)] 2 ( 1 ) and [Sn( n -Bu) 2 (HL)(H 2 O)] 2 ( 2 ) derived from the Schiff base 2-[(2,3-dihydroxyphenyl)methylideneamino]benzenesulfonic acid trihydrate ( H 3 L·3H 2 O ) are described. The monoprotonated form (HL 2− ) of the Schiff base behaves as O,O′-bidentate ligand, chelating the metal by the two phenoxo oxygen atoms. The hexacoordinated metal centr...
View next paperAntiproliferative and anti-tumor activity of organotin compounds