Selective fluorometric detection of pyrophosphate by interaction with alizarin red S–dimethyltin(iv) complex

Villamil‐Ramos, Raúl; Yatsimirsky, Anatoly K.

doi:10.1039/c0cc05346e

Cited by 44 publications

(18 citation statements)

References 22 publications

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“…Expectedly, the fluorescence of diamine precursors L 1 , L 2 , L 3 , L 4 , L 5 , L 6 (except L 2 ) is quenched upon the formation of respective binuclear complexes with Ph 2 Sn(IV). This fluorescence quenching behaviour of binuclear Ph 2 Sn(IV) dithiocarbamate complexes is consistent with the fluorescence behaviour of flavonoid organotin(IV) derivatives, which are reportedly fluorescent when they are penta‐coordinate, but non‐fluorescent when they are hexa‐coordinate . Further, it appears that the fluorescence of the compounds is greatly affected by the molecular arrangements, conformational stiffness of the fluorophore and non‐covalent interactions.…”

Section: Resultssupporting

confidence: 80%

Diphenyltin(IV) dithiocarbamate macrocyclic scaffolds as potent apoptosis inducers for human cancer HEP 3B and IMR 32 cells: synthesis, spectral characterization, density functional theory study andin vitrocytotoxicity

Kadu

Roy

Singh

2015

Applied Organom Chemis

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Binuclear diphenyltin(IV) dithiocabamate macrocyclic complexes [(Ph2SnIV)2‐μ2‐bis{(κ2S,S‐S2CN(R)CH2CONHC6H4)2O}] (R = iPr (1), sBu (2), nBu (3), Cy (4), 2‐furfuryl (5) or benzyl (6)) were synthesized through a self‐assembly process involving novel diamino precursors 4,4′‐bis(2‐(alkylamino)acetamido)diphenyl ethers (L1, L2, L3, L4, L5, L6), CS2 and Ph2SnCl2. These were characterized using microanalysis and relevant spectroscopic methods. The geometry of all compounds was optimized using the density functional theory method. In vitro cytotoxic activity was evaluated against HEP 3B (hepatoma) and IMR 32 (neuroblastoma) using the MTT assay. Notably, complexes 1, 2, 3, 4, 5, 6 were found to be extremely active against both cell lines and cytotoxicity data confirmed their 16‐fold better potency compared to cisplatin, a well‐known antineoplastic drug. Flow cytometric analysis of annexin V–propidium iodide‐stained cells demonstrated the ability of L5, 4 and 6 to induce apoptosis in HEP 3B and IMR 32 cells, required for major therapeutic implication in cancer therapy. The extraordinary potency of binuclear complex 4 can be correlated with higher LUMO energy together with the greatest value of residual charge on the Sn(IV) centre among the compounds under investigation. Copyright © 2015 John Wiley & Sons, Ltd.

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Section: Resultssupporting

confidence: 80%

Diphenyltin(IV) dithiocarbamate macrocyclic scaffolds as potent apoptosis inducers for human cancer HEP 3B and IMR 32 cells: synthesis, spectral characterization, density functional theory study andin vitrocytotoxicity

Kadu

Roy

Singh

2015

Applied Organom Chemis

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“…1 A 3 . Selected bond lengths ( A) and angles ( ): Sn1-O2 2.062(8), Sn1-C22 2.121(12), Sn1-C16 2.134(13), Sn1-O1 2.242(9), Sn1-Cl2 2.401(4), O1-C1 1.235(15), O2-C2 1.325( 14), O2-Sn1-C22 119.0(4), O2-Sn1-C16 111.7(4), C22-Sn1-C16 127.0(4), O2-Sn1-O1 74.9(3), C22-Sn1-O1 88.9(4), C16-Sn1-O1 89.7(4), O2-Sn1-Cl2 86.3(3), C22-Sn1-Cl2 99.2(4), C16-Sn1-Cl2 98.7(4), O1-Sn1-Cl2 161.1(2), C1-O1-Sn1 113.1(9), C2-O2-Sn1 116.1(8), C3-O3-C4 120.5 (11). X-ray diffraction studies were performed on a Bruker-APEX diffractometer with a CCD area detector, Mo Ka-radiation, l ¼ 0.71073 A, graphite monochromator.…”

Section: -Hydroxyflavonate-diphenyltin(iv)mentioning

confidence: 99%

“…2,10 Recently we described fluorometric PPi detection with a dimethyltin(IV) complex of Alizarin Red S (1) with a detection limit of 3 mM and high selectivity in respect to both Pi and ATP. 11 Using ''hard'' Sn(IV) as a recognition Lewis acid site may have some advantages over Zn(II) and Cu(II) because of its possible higher selectivity to hard anions manifested e.g. in reported selectivity toward phosphate or fluoride anions with organotin(IV) compounds used as anion ionophores in polymeric membrane ion-selective electrodes.…”

Section: Introductionmentioning

confidence: 99%

Selective fluorometric detection of pyrophosphate by 3-hydroxyflavone-diphenyltin(iv) complex in aqueous micellar medium

Villamil‐Ramos

Barba

Yatsimirsky

2012

Analyst

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3-Hydroxyflavonate-diphenyltin(IV) chloride (Ph(2)Sn(Ofl)Cl) was prepared and characterized structurally by single crystal X-ray diffraction. The compound possesses high fluorescence (λ(max) 464 nm with excitation at 400 nm) in neutral aqueous solutions containing 5 mM cetyltrimethylammonium chloride and does not lose the flavonol ligand even at high dilution. The fluorescence is selectively quenched by pyrophosphate (PPi) (linear range 0-5 μM, detection limit 0.1 μM). Determination of 1 μM PPi tolerates the presence of 100-fold excess of AMP, ADP, inorganic phosphate and acetate, and 10-fold excess of ATP. From concentration profiles of the quenching effect it is concluded that quenching occurs due to formation of the complex (Ph(2)Sn(Ofl))(3)PPi, which is transformed at higher PPi concentrations to a simple 1 : 1 complex Ph(2)Sn(Ofl)(PPi). No flavonol ligand exchange with PPi is observed. A series of related organotin(IV) complexes were prepared in situ by reacting 3-hydroxyflavone with Me(2)SnCl(2), PhSnCl(3) and n-BuSnCl(3). The derivatives of Me(2)SnCl(2) and PhSnCl(3) behave similarly to Ph(2)Sn(Ofl)Cl but with lower sensitivity to PPi. However, the n-butyltin(IV) derivative tentatively of the composition n-BuSn(Ofl)(2) undergoes fluorescence enhancement rather than quenching in the presence of PPi in the μM concentration range. The results of this study demonstrate that the use of metal flavonol complexes as optical sensors for anions is a promising approach.

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“…Due to the strong interaction of PPi with metal complexes or charged compounds, to date, diverse colorimetric and fluorescent sensors for PPi have been developed using organic probes and nanomaterials such as silica nanoparticles, gold nanoparticles, graphene oxide and magnetic nanoparticles . As PPi has a strong affinity for Cu 2+ with a stability constant (K) of logK Cu.PPi = 12.45), Deng and colleagues proposed a Au‐NP‐based colorimetric method for PPi.…”

Section: Introductionmentioning

confidence: 99%

Signal‐on fluorescence assay for pyrophosphate ions based on DNA‐stabilized silver nanoclusters

Zhang

et al. 2019

Luminescence

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Pyrophosphate anion (P 2 O 7 4− , PPi) is considered as a potential biomarker for arthritic diseases because high levels of PPi may result in calcium pyrophosphate dehydrate crystal deposition diseases. In this study, a simple fluorescence method for PPi was demonstrated by organic integration of the efficient fluorescence quenching ability of copper ions to DNA-scaffolded silver nanoclusters and the strong affinity of PPi towards copper ions. This simple fluorescence sensor showed a low detection limit (0.28 μM based on signal/noise = 3) towards the detection of PPi. Practical application of this method was also validated by detection of PPi in the synovial fluid.

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Selective fluorometric detection of pyrophosphate by interaction with alizarin red S–dimethyltin(iv) complex

Abstract: Highly selective detection of pyrophosphate in the presence of inorganic phosphate, halides, acetate, ATP, other nucleotides and phosphate esters in neutral aqueous solutions is achieved by using fluorescent dimethyltin(iv)-alizarin red S complex.

Cited by 44 publications

References 22 publications

Diphenyltin(IV) dithiocarbamate macrocyclic scaffolds as potent apoptosis inducers for human cancer HEP 3B and IMR 32 cells: synthesis, spectral characterization, density functional theory study andin vitrocytotoxicity

Diphenyltin(IV) dithiocarbamate macrocyclic scaffolds as potent apoptosis inducers for human cancer HEP 3B and IMR 32 cells: synthesis, spectral characterization, density functional theory study andin vitrocytotoxicity

Selective fluorometric detection of pyrophosphate by 3-hydroxyflavone-diphenyltin(iv) complex in aqueous micellar medium

Signal‐on fluorescence assay for pyrophosphate ions based on DNA‐stabilized silver nanoclusters

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