The protection of Nifedipin from photodegradation due to complex formation with β-cyclodextrin

Nikolić, Vesna; Ilić, Dušica P.; Nikolić, Ljubiša; Stanković, Miomir; Cakić, Milorad D.; Stanojević, Ljiljana P.; Kapor, Á.; Popsavin, Mirjana

doi:10.2478/s11532-010-0043-x

Cited by 12 publications

(5 citation statements)

References 20 publications

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“…[32], the band peaking at 310 nm is characteristic of nitroso compounds. The decrease in the absorbance of the band attributed to the electronic transition of the -NO 2 group has its origin in the photo-transformation of NIF in 4-(2-nitrosophenyl)-2.6-dimethyl-3.5-dimethoxy carbonyl pyridine [20,31]. These variations indicate changes in the electronic transitions of NIF, in good agreement with Refs.…”

Section: Resultssupporting

confidence: 90%

“…(e,f) show UV-VIS spectra of the samples of NIF (black curves), 2 mL NIF 0.6 mM + 1 mL NaOH 0.3M (red curves), 1.5 mL NIF 0.6 mM + 1.5 mL NaOH 0.3M (green curves) and 1 mL NIF 0.6 mM + 2 mL NaOH 0.3M (blue curves) before and after 136 min of UV irradiation, respectively. NIF in 4-(2-nitrosophenyl)-2.6-dimethyl-3.5-dimethoxy carbonyl pyridine [20,31]. These variations indicate changes in the electronic transitions of NIF, in good agreement with Refs.…”

Section: Resultssupporting

confidence: 89%

“…Early studies showed that (i) NIF, i.e., 1, 4-dihydro-2.6-dimethyl-4-(2-nitrophenyl)-3,5-pyridine carboxylate, by exposure to UV light, is transformed into 4-(2-nitrosophenyl)-2.6-dimethyl-3.5-dimethoxy carbonyl pyridine and 4-(2-nitrophenyl)-2.6-dimethyl-3.5-dimethoxy carbonyl pyridine [20]; (ii) under in vitro conditions, NIF is sensitive to UV light, leading to nitroso derivatives which subsequently can react, resulting in compounds of the lactam type, according to high-purity liquid chromatography (HPLC) analysis [21]; (iii) NIF in the presence of hemoglobin at pH > 10 is unstable [22]; and (iv) pH changes alter the sensitivity of vascular tissue to NIF in the case of ischemia, inhibiting contractions induced by the agonist [23]. A removal rate of NIF of 65% was induced by photodegradation processes [24], while in the presence of UV light and H 2 O 2 , the NIF removal rate was increased to 99.94% [25].…”

Section: Introductionmentioning

confidence: 99%

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Complex Spectroscopy Studies of Nifedipine Photodegradation

Paraschiv,

Daescu,

Bartha

et al. 2023

Pharmaceutics

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The aim of this work is to highlight the influence of UV light on the hydrolysis reaction of nifedipine (NIF) in the presence of alkaline solutions. In this context, the photodegradation of NIF in the absence of alkaline solutions caused (a) a change in the ratio between the absorbances of three bands in the UV-VIS spectra localized at 224–240 nm, 272–276 nm and 310–340 nm, assigned to the electronic transitions of -COOCH3 groups, -NO2 groups and a heterocycle with six atoms; (b) a red-shift of the photoluminescence (PL) band from 458 nm to 477 nm, simultaneous with an increase in its intensity; (c) a decrease in the ratio of the Raman line intensities, which peaked at 1224 cm−1 and 1649 cm−1, associated with the vibrational modes of -C-C-O in the ester group and C=C stretching; and (d) a decrease in the ratio between the absorbances of the IR bands, which peaked at 1493 cm−1 and 1223 cm−1, associated with the vibrational modes of the -NO2 group and C-N stretching. These changes were explained considering the NIF photodegradation reaction, which leads to the generation of the compound 4-(2-nitrosophenyl)-2.6-dimethyl-3.5-dimethoxy carbonyl pyridine. The interaction of NIF with NaOH in the absence of UV light was demonstrated to induce changes in the vibrational mode of the -C-C-O bond in the ester group. The photodegradation of NIF after its reaction with NaOH induces significant changes highlighted in its (a) UV-VIS spectra, by the shift of the absorption band at 238 nm; (b) PL spectra, by the supraunitary value of the ratio between the emission band intensities at 394–396 nm and 450 nm; (c) Raman spectra, by the change in the ratio between the intensities of the lines that peaked at 1224 cm−1 and 1649 cm−1 from 0.61 to 0.49; and (d) FTIR spectra, by the lowered absorbance of the IR band at 1493 cm−1 assigned to the vibrational mode of the -NO2 group as a result of the generation of the nitroso compound. These changes were explained considering the hydrolysis reaction products of NIF, as the nitroso compound is converted to a lactam-type compound. The photodegradation reaction rate constants of NIF and NIF after interaction with NaOH were also reported. The decrease in thermal stability of NIF samples after interaction with NaOH, as well as of NIF after exposure to UV light compared to NIF prior to exposure to UV light, was demonstrated by thermogravimetry, and the key fragments were confirmed by mass spectrometry.

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Section: Resultssupporting

confidence: 90%

Section: Resultssupporting

confidence: 89%

Section: Introductionmentioning

confidence: 99%

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Complex Spectroscopy Studies of Nifedipine Photodegradation

Paraschiv,

Daescu,

Bartha

et al. 2023

Pharmaceutics

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“…In an aqueous solution nonpolar aliphatic and aromatic molecules of appropriate size may enter the hydrophobic cavities of cyclodextrins [18]. As complexing agents they are capable of enhancing solubility, photostability, volatility and bioavailability of various drugs, e.g., nifedipine [19], amlodipin besylate [20], atenolol [21] or allicin [22]. Because of better solubility at room temperature than β-cyclodextrin, in this study, 2-hydroxypropyl-β-cyclodextrin was chosen (Figure 1).…”

Section: Piroxicammentioning

confidence: 99%

Photostability of piroxicam in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

Nikolić¹,

Ilić‐Stojanović²,

Nikolic³

et al. 2014

Hem Ind

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The aim of this work is the protection of piroxicam from photodegradation by forming inclusion complex with 2-hydroxypropyl-β-cyclodextrin. Piroxicam:2-hydroxypropyl-βcyclodextrin molecular inclusion complex was prepared by coprecipitation method with 1:1 molar ratio. Structural characterization of the complex, the corresponding physical mixture and complexing agents of piroxicam and 2-hydroxypropyl-β-cyclodextrin was carried out by X-ray diffraction (XRD), proton nuclear magnetic resonance (1 H-NMR) and Fourier transform infrared spectroscopy (FTIR). Photosensitivity to daylight of piroxicam and piroxicam:2-hydroxypropyl-β-cyclodextrin inclusion complex was investigated by FTIR. The investigations show that higher photostability of piroxicam was achieved in the complex than in non-complexed piroxicam.

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“…The inclusion complexes of cyclodextrin and its derivatives were used to improve the physical and chemical properties of the drugs (solubility, vapor, odor, stability, etc.). A great number of researches proved that the solubility and stability of the drugs are increased, e.g., atenolol [12][13][14], nifedipine, nicardipine [15][16][17], amlodipine [18,19] and allicin [20]. The solubility of the usnic acid was improved by complexation with β-cyclodextrin (β-CD:UA) which is incorporated in liposomes [21].…”

mentioning

confidence: 99%

The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

Ilić‐Stojanović¹,

Nikolić²,

Nikolić³

et al. 2015

Hem Ind

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The aim of this work was the preparation of the inclusion complex of naproxen with 2hydroxypropyl-β-cyclodextrin (HP-β-CD) in order to improve the physical and chemical properties of naproxen. The molecular inclusion complexes of naproxen with HP-β-CD were prepared by using the co-precipitation method in the solid state with the molar ratio of 1:1. The structure of the obtained complex was characterized by using FTIR, 1 H NMR, UV-Vis and XRD methods. The testing of naproxen photostability by the UV-Vis method indicated the degradation to aromatic ketone, 2-acetyl-6-methoxynaphthalene. FTIR analysis showed that the degradation has started 15 days after the exposure of naproxen to daylight while the inclusion complex of naproxen:2-hydroxypropyl-β-cyclodextrin was photostable for a period of 30 days.

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The protection of Nifedipin from photodegradation due to complex formation with β-cyclodextrin

Cited by 12 publications

References 20 publications

Complex Spectroscopy Studies of Nifedipine Photodegradation

Complex Spectroscopy Studies of Nifedipine Photodegradation

Photostability of piroxicam in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin

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