Synthesis and characterization of di-phenyl-tinIV-salicyliden-ortho-aminophenols: Analysis of in vitro antitumor/antioxidant activities and molecular structures

Beltrán, Hiram I.; Damián-Zea, Carlos; Hernández‐Ortega, Simón; Nieto‐Camacho, Antonio; Ramírez‐Apán, María Teresa

doi:10.1016/j.jinorgbio.2007.04.002

Cited by 58 publications

(30 citation statements)

References 61 publications

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“…FT IR spectroscopic studies: IR spectra (see ESI, Figures S6-S10) of compounds 1-3 show two intense bands for the C=N fragment between 1607-1601 and 1568-1535 cm -1 [36,37]. These stretching frequencies are indirect evidences of the nature of the solid state structures as proven by X-ray crystallography for compound 2.…”

Section: X-ray Crystallographic Studies Of Compoundmentioning

confidence: 97%

“…The results suggested biological specificity towards U251, MCF-7 and SKLU-1 cancer cells at doses below 2.5 µM; which are lower than the IC 50 value of cisplatin. Since the inhibitory concentration values for the series were similar to Ph 2 SnCl 2 , it was concluded that only the Ph 2 Sn moiety was responsible for those activities [36].…”

Section: Introductionmentioning

confidence: 94%

“…Seven di-phenyltin(IV) compounds [36] were assessed as new anticancer agents against six human tumour cell lines U251, PC-3, K-562, HCT-15, MCF-7 and SKLU-1 [36]. The results suggested biological specificity towards U251, MCF-7 and SKLU-1 cancer cells at doses below 2.5 µM; which are lower than the IC 50 value of cisplatin.…”

Section: Introductionmentioning

confidence: 99%

“…In accordance with previous studies, the aim of this study is to evaluate the in vitro effect (cytotoxicity) of these novel compounds against five human tumour cell lines. This is accomplished by comparing the efficacies of these compounds with the known non-azo containing complex 2,2-diphenyl-6-aza-1,3-dioxa-2-stanna-[d,h]dibenzocyclononene (compound 1) as reported by Beltrán and co-workers [36].…”

Section: Introductionmentioning

confidence: 99%

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An in vitro study on the effect of synthesized tin(IV) complexes on glioblastoma, colorectal, and skin cancer cell lines

Williams¹,

Lewis-Alleyne²,

Solomon³

et al. 2016

Biomed Res Clin Prac

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Abstract((E)-2-(2-hydroxybenzylideneamino)phenolato-2,2-diphenyl-6-aza-1,3-dioxa-2-stanna- [d,h] dibenzocyclononene, [Sn(Ph 2 SB)] (compound 1, where Ph 2 SB=(E)-2-(2-hydroxybenzylideneamino)phenolato Schiff base) and two novel compounds, [[SnPh 2 (F-azoSB)] (compound 2, where F-azoSB=4-((E)-(4-fluorophenyl) diazenyl)-2-((E)-(2-hydroxyphenylimino)methyl)phenolato Schiff base), [[SnPh 2 (sulf-azoSB)]0.125CHCl 3 (compound 3, where sulfamerazineazosalSB=4-((E)-(4-hydroxy-3-((E)-(2-hydroxyphenylimino)methyl)phenyl)diazenyl)-N-(4-methylpyrimidin-2-yl) benzenesulfonamide Schiff base), and the control compound, cisplatin (compound 4) were analysed to comparatively determine their effect on cancer cell growth. Anti-cancer properties of compounds 1-4 were examined using glioblastoma (U-1242 MG), colorectal (HT-29 and HCT-116), and skin (A431) human cancer cell lines. With regards to human glioblastoma cells, compounds 1 and 3 demonstrated anti-proliferative capacity in the cell line tested. Specifically, compounds 1 and 3 inhibited cell proliferation by 50% at concentrations between 10 and 50 µM. With respect to colon cancer cell lines, the IC 50 values for compounds 1-3 ranged from 3.04 ± 0.98 to 104.51 ± 13.87 µM. In the case of HCT-116, this translates to a 3-to 73-fold inhibitory effect of compounds 1-3 over cisplatin. In all cell lines tested, the chemo-effect was more pronounced with compounds 1-3 than with the control (compound 4); demonstrating that these azo-containing Sn(IV) complexes were more potent than compound 4. The overall effect of compounds 1-3 in the induction of appotosis and the inhibition of proliferation have defined an essential role for these compounds in chemotherapy. IntroductionFrom the late 1960s until the present, there have been significant advances in both the early detection and the treatments of cancer. Despite these advances overall incidences of cancer and deaths from cancer have increased during the same period [1]. These counterintuitive increases have been the impetus for development of new drugs for cancer treatment. In this context the organometallic compounds have been widely investigated as potential anti-tumour agents. Metallocene dihalide complexes Cp 2 MX 2 (where M=titanium, vanadium, niobium, or molybdenum) were the first early transition metal complexes that were shown to have anti-tumour activity. In addition, the organometallic-DNA and organometallic-nucleic acid interactions of these compounds have also been investigated [2][3][4]. More recently, ferricenium salts, organotin, and bismuth complexes have also emerged as examples of organometallic compounds that have been found to exhibit interesting anti-tumour activity [5].The biological activity of organotin compounds has become well known due to their practical applications as fungicides, bactericides, biocides, and pesticides [3,[6][7][8]. It is now well established that organotin compounds are very important in cancer chemotherapy [9] and as potential anti-cancer agents [10][11][12][13]. This is due in part to thei...

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Section: X-ray Crystallographic Studies Of Compoundmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

An in vitro study on the effect of synthesized tin(IV) complexes on glioblastoma, colorectal, and skin cancer cell lines

Williams¹,

Lewis-Alleyne²,

Solomon³

et al. 2016

Biomed Res Clin Prac

View full text Add to dashboard Cite

show abstract

“…On the other hand, di-phenyltin(IV) derivatives often are less toxic than other di-organo-tin(IV) derivatives [52][53][54]. It is interesting that 3 has remarkable activity towards P. aeruginosa while, the bacteria of the genus…”

Section: Antibacterial Studiesmentioning

confidence: 99%

Diorganotin(IV) complexes with 2-furancarboxylic acid hydrazone derivative of benzoylacetone: Synthesis, X-ray structure, antibacterial activity, DNA cleavage and molecular docking

Sedaghat

Ebrahimi

Carlucci

et al. 2015

Journal of Organometallic Chemistry

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Effect of diorganotin(IV) carboxylate complexes, [N‐(2‐carboxyphenyl) salicylideneiminato]dimethyltin(IV), bis(µ₃‐oxo)bis(µ‐O‐aminobenzoato‐O,O′) bis(O‐aminobenzoato)tetrakis[dimethyltin(IV)] and bis(O‐aminobenzoato‐O,O′) di‐n‐butyltin(IV), on the membrane of Candida albicans cells—a mechanistic investigation of the antifungal activity of organotin complexes

Vieira

Menezes

Lima

et al. 2008

Applied Organom Chemis

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The in vitro anti‐fungal activity of diorganotin(V) carboxylate complexes, [N‐(2‐carboxyphenyl)salicylideneiminato] dimethyltin(IV) (1), bis(µ3‐oxo)bis(µ‐O‐aminobenzoato‐O,O′)bis(O‐aminobenzoato)tetrakis[dimethyltin(IV)] (2) and bis(O‐ aminobenzoato‐O,O′)di‐n‐butyltin(IV) (3) has been screened against Candida albicans. The complexes, prepared by minor modifications of a literature method, have been fully characterized. The biological activities of complexes 1–3 on cultures of Candida albicans have been studied and the related mechanism has been investigated. No changes in DNA integrity or in the mitochondria function have been observed. However, all the tin compounds were found to reduce the ergosterol biosynthesis. The compounds have inhibitory concentrations (IC50) in the range of 7.5–20.0 µg ml−1, with compound 3 the most active. These results were compared with those provided by the literature, using myconazole, amphotericin B and fluconazole as standards. Scanning electron microscopy and transmission electron microscopy of the cells treated with complexes 1–3, revealed severe damage on the C. albicans cells compromising the cellular integrity, suggesting that the organotin complexes act on the cell membrane, in view of cytoplasm leaking and cellular deformation. The data indicate for 1–3 a mechanism of action similar to that of azole drugs, such as ketoconazole or fluconazole, normally used in Candida infections. Copyright © 2008 John Wiley & Sons, Ltd.

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Synthesis and characterization of di-phenyl-tinIV-salicyliden-ortho-aminophenols: Analysis of in vitro antitumor/antioxidant activities and molecular structures

Cited by 58 publications

References 61 publications

An in vitro study on the effect of synthesized tin(IV) complexes on glioblastoma, colorectal, and skin cancer cell lines

An in vitro study on the effect of synthesized tin(IV) complexes on glioblastoma, colorectal, and skin cancer cell lines

Diorganotin(IV) complexes with 2-furancarboxylic acid hydrazone derivative of benzoylacetone: Synthesis, X-ray structure, antibacterial activity, DNA cleavage and molecular docking

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