Determination of liposome permeability of ionizable carbamates of zidovudine by steady state fluorescence spectroscopy

Raviolo, Mónica A.; Sánchez, Julieta M.; Briñón, Margarita C.; Perillo, Marı́a A.

doi:10.1016/j.colsurfb.2007.08.004

Cited by 14 publications

(7 citation statements)

References 41 publications

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“…Azides 7 – 11 which comprise positively and negatively side chains, aromatic substituents and a neutral thymine, were used to encompass several types of interaction modes, including π – π stacking, electrostatic and hydrogen bonding, with the aim of maximizing the probability of identifying a suitable G4 ligand 38 . We note that zidovudine ( 11 ) is a clinical drug approved by the Food and Drug Administration (FDA) 39 , it is a deoxythymidine derivative which may interact with other nucleic acid bases on the loop of G4s through hydrogen-bond interactions. Figure 1 illustrates the synthetic route for the strategically designed compounds ( 1–6 ).…”

Section: Resultsmentioning

confidence: 99%

Development of squaraine based G-quadruplex ligands using click chemistry

Zhang

Wei

Bing

et al. 2017

Sci Rep

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The G-quadruplex (G4) structures of nucleic acids are considered to play an intrinsic role in gene expression. To this end, the development of new G4 ligands has attracted extensive research interests towards potential applications as G4-targeted drugs and molecular probes. To date, the majority of G4 ligands have been composed of an extended planar aromatic scaffold that interacts with the terminal G-tetrad plane via π-π interactions, and various side chains that interact with the sugar-phosphate backbone, loops or grooves of the G4 structures. The side chains act to modulate the affinity and selectivity of the G4 ligands, alongside influencing their biodistribution. Here, we present a click chemistry methodology to generate a series of squaraine-based G4 ligand derivatives based on our previously reported G4 probe (named CSTS) but with varing side chains. We find that importantly these new G4 ligand derivatives retain the G4 selectivity, optical properties and low cytotoxicity of CSTS, but exhibit different binding behaviors to G4 structures, and distinct cellular uptake efficiencies. Indeed, of these new complexes, several exhibit much higher affinity and cellular uptake than CSTS. Overall, this novel, facile and highly effective strategy has significant future potential for the high-throughput screening of G4 ligands or probes targeted towards in vivo applications.

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Section: Resultsmentioning

confidence: 99%

Development of squaraine based G-quadruplex ligands using click chemistry

Zhang

Wei

Bing

et al. 2017

Sci Rep

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“…These studies were performed since they are important early requirements for novel compounds in drug research. Previously, we also have reported the lipophilicity and liposome permeability of 2–6 [ 7 , 19 ].…”

Section: Introductionmentioning

confidence: 98%

Preformulation Studies of Zidovudine Derivatives: Acid Dissociation Constants, Differential Scanning Calorimetry, Thermogravimetry, X-Ray Powder Diffractometry and Aqueous Stability Studies

Raviolo

Briñón²

2011

Sci. Pharm.

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As part as of the preformulation studies of new 5′-OH derivatives of zidovudine, compounds 2–6, their acid dissociation constants, Differential Scanning Calorimetry (DSC) and Thermogravimetry (TG) curves, X-Ray Powder diffractograms and aqueous stability are reported. A sensitive technique such as differential scanning potentiometry was used to determine the pKa constants of the above mentioned compounds. In addition, pKa values were calculated from theoretical methods, and no significant differences with those of experimental ones were observed. X-Ray Powder Diffractometry data demonstrated that compounds 2–4 were crystalline while 5 and 6 were amorphous. DSC analysis indicated that all of them presented an exothermic decomposition peak above 150 °C which is accompanied by a weight loss in the respective TG curves. The stability of these compounds in aqueous medium at different pH values was investigated, using a validated High Performance Liquid Chromatography (HPLC) method, which demonstrated to be rapid, selective, sensitive, accurate and stability-indicating. Good recovery, linearity and precision were also achieved. For all compounds the aqueous hydrolysis followed a pseudo-first-order kinetics, depending on pH and the union existing between AZT and the associate moiety. The hydrolysis was catalyzed by hydroxide ion in the 7.4–13.2 pH range, while all compounds exhibited pH-independent stability from acidic to neutral media (pHs 1.0–7.4).

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“…Several methods have been discovered for the quantitative determination of zidovudine including chromatog- raphy [9][10][11][12][13][14][15], fluorescence polarization immunoassay [16], using diamond paste based immunosensor [17], fluorescence spectroscopy [18] and voltammetry [19][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Determination of the Antiretroviral Drug Zidovudine in Diluted Alkaline Electrolyte by Adsorptive Stripping Voltammetry at the Mercury Film Electrode

Castro¹,

Aucélio²,

Rey³

et al. 2011

AJAC

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This paper describes a stripping method for the determination of zidovudine at the submicromolar concentration levels. This method is based on the controlled adsorptive accumulation of zidovudine at the thin-film mercury electrode, followed by a linear-sweep stripping voltammetry measurement of the surface species. Optimal experimental conditions include a NaOH solution of 2.0 × 10 -3 mol·L -1 (supporting electrolyte), an accumulation potential of -0.30 V and a scan rate of 100 mV·s -1 . The response of zidovudine is linear over the concentration range 0.01 -0.08 ppm. After an accumulation time of 5 minutes, the detection limit was found to be 0.67 ppb (2.5 × 10 -9 mol·L -1 ). More convenient methods to measure zidovudine concentration in the presence of the didanosine, acyclovir, nevirapine, lamivudine, and efavirenz, were also investigated. The presence of zidovudine together with ATP or ssDNA demonstrates the utility of this method.

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Determination of liposome permeability of ionizable carbamates of zidovudine by steady state fluorescence spectroscopy

Cited by 14 publications

References 41 publications

Development of squaraine based G-quadruplex ligands using click chemistry

Development of squaraine based G-quadruplex ligands using click chemistry

Preformulation Studies of Zidovudine Derivatives: Acid Dissociation Constants, Differential Scanning Calorimetry, Thermogravimetry, X-Ray Powder Diffractometry and Aqueous Stability Studies

Determination of the Antiretroviral Drug Zidovudine in Diluted Alkaline Electrolyte by Adsorptive Stripping Voltammetry at the Mercury Film Electrode

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