Evaluation of the photoprotective effect of β-cyclodextrin on the emission of volatile degradation products of ranitidine

Jamrógiewicz, Marzena; Wielgomas, Bartosz; Strankowski, Michał

doi:10.1016/j.jpba.2014.05.014

Cited by 13 publications

(9 citation statements)

References 18 publications

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“…An enhanced solubility, both in water and in organic solvents, was also attributed to DIMEB and TRIMEB CDs. Indeed, the formation of DIMEB CD and TRIMEB CD inclusion complexes are reported, for example, by Yu et al [ 16 ] and Nishijo et al [ 17 ], respectively, indicating that they have potential uses as carriers for different drugs for medical applications [ 18 – 19 ]. In fact, for pharmaceutical applications, the improvement of drug stability and solubility play a key role [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

“…The use of a delivery system could be a method to improve the photochemical behavior and to prevent the degradation of the thiobase [ 27 ]. In fact, literature suggests that one method to avoid the drug degradation is the complexation with CDs, and, as described in [ 18 ], the preparation of simple physical mixtures with CDs was already shown to be effective in terms of protective activity. Starting from these considerations, the main goal of this work is to study the ability of the modified nucleoside S 4 TdR to form inclusion complexes with five CDs: 2-HP-α-CD, 2-HP-β-CD, 2-HP-γ-CD, DIMEB and TRIMEB.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

Rizzi¹,

Matera²,

Semeraro³

et al. 2016

Beilstein J. Org. Chem.

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SummarySince several years the inclusion of organic compounds (guests) within the hydrophobic cavity (host) of cyclodextrins (CDs) has been the subject of many investigations. Interestingly, the formation of inclusion complexes could affect the properties of the guest molecules and, for example, the influence of the delivery system can be a method to improve/change the photochemical behavior of the guest. In particular, very recent studies have shown the protective role of CDs preventing the degradation of the encapsulated guest. Starting from this consideration, in this work, only the structure and complexation mode of the inclusion complexes involving 4-thiothymidine (S4TdR, a known photosensitizer) and five CDs, namely 2-hydroxypropyl-α-cyclodextrin (2-HP-α-CD), 2-hydroxypropyl-β-cyclodextrin (2-HP-β-CD), 2-hydroxypropyl-γ-cyclodextrin (2-HP-γ-CD), heptakis-(2,6-di-O-methyl)-β-cyclodextrin (DIMEB CD) and heptakis-(2,3,6-tri-O-methyl)-β-cyclodextrin (TRIMEB CD) were investigated by different spectroscopic techniques (UV–vis, FTIR–ATR, 1H NMR) and cyclic voltammetry analysis (CV). This work is necessary for a prospective research on the photoreactivity of S4TdR in aqueous environment and in the presence of CDs to prevent its degradation under irradiation. UV–vis, FTIR–ATR and CV measurements suggested the formation of supramolecular structures involving the employed CDs and mainly the pyrimidine ring of S4TdR. 1H NMR analyses confirmed such indication, unveiling the presence of inclusion complexes. The strongest and deepest interactions were suggested when TRIMEB and DIMEB CDs were studied. The S4TdR affinity towards CDs was also evaluated by using the Benesi–Hildebrand (B–H) equation at 25 °C employing CV and 1H NMR methods. The stoichiometry of the interaction was also inferred and it appears to be 1:1 for all examined CDs.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

Rizzi¹,

Matera²,

Semeraro³

et al. 2016

Beilstein J. Org. Chem.

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“…Konposatu organiko hegazkorren analisirako, aldiz, erauzketa-teknika mota ezberdinak erabil daitezke: buruguneko erauzketa (Headspace, HS) [31,32], buruguneko erauzketa dinamikoa (Dynamic Headspace, DHS) [26], burugune anitzeko erauzketa (Multiple Headspace, MHS) [29,30], fase solidoko mikroerauzketa (Solid Phase Microextraction, SPME) [26,29,30,33] eta irabiagailu magnetikoaren bidezko erauzketa solidoa (Stir Bar Sorptive Ex-Bioziden mikrokapsularatzea eta ingurumen-osasuna traction, SBSE) [26]. Erauzketa burutu ondoren, analisia aurrera eramateko gehienetan gas-kromatografia (Gas chromatography, GC) erabiltzen da, konposatuen propietateen arabera detektore mota ezberdinetara akoplatuta egon daitekeena [26,[29][30][31][32][33]. Detektore erabilienen artean gar bidezko ionizazio bidezko detektorea (Flame ionization detector, FID) [31,32] edota masa-espektrometria (MS) [28][29][30] aurkitzen dira, azken urteetan azken horren erabilera areagotzen ari delarik.…”

Section: Askapenaren Ikerketaunclassified

Bioziden mikrokapsulazioa eta ingurumen-osasuna

Alonso

Corral

2017

EKAIA

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Laburpena: XXI. mendeko erronken artean, ingurumen-osasunean kalte egin dezaketen arazoei aurre egiteko metodo alternatiboen bilaketa aurkitzen da. Arlo honetan, mikrokapsularatzearen abantaila anitzek arazo horiei aurre egiteko baliozko aukera bat erakusten dute. Abantaila garrantzitsu horien artean aurkitzen dira ingurumenean eta ugaztunetan toxikotasuna murriztea, langileen zein bezeroen manipulazioan segurtasuna hobetzea eta uretan disolbagarritasun baxua duten konposatuen sintesia uretan ahalbidetzea. Horrela, ura disolbatzaile gisa erabiliz, disolbatzaile organiko toxikoen eta garestien erabilpena ekiditen da.Gure ikerkuntza-taldeak intsektuen izurriteen kontroleko amuen parte izango diren produktu mikrokapsularatuak sintetizatu ditu. Mikrokapsularatutako produktu horiek biozida eta bioerakarle naturalak dituzte, ingurumenarentzat zein gizakiarentzat errespetagarriagoa den produktua lortzeko asmoz. Gainera, bioerakarleen erabilpenaren ondorioz, amaierako produktu komertziala selektiboagoa eta eraginkorragoa izango da espezie zehatz batzuen aurka.Mikrokapsularatutako biozidak sinergisten familiako pestizidak dira. Adibide ezagun bat piperonilo butoxidoa da. Biozidek intsektiziden, (piretroideak, nikotinoideak, karbamatoak...), fungiziden (tebukonazola) zein pestiziden gaitasuna areagotzeko gaitasuna dute. Bioerakarle naturalak, berriz, alkoholen eta terpenoen familiako konposatu hegazkorrak dira. Mikrokapsularatze-metodo arinak eta errendimendu estekiometriko altukoak garatu izan dira polimeroekin, gomekin eta karbohidratoekin erabiltzeko, hala nola ihinztadura bidezko lehorketa, gelifikazio ionikoa eta inklusio-konplexuen eraketako mikrokapsularatze-metodoak. Era berean, konposatu aktiboen kontzentrazioak determinatzeko, metodologia analitiko ezberdinak ikertu dira eta buruguneko gas-kromatografia / masa-espektrometria detektoreko (Headspace Gas Chromatography-Mass Spectrometry, HS-GC/MS) teknika erabiliz giro-tenperaturan eta hezetasunean konposatu hegazkorren askapenaren monitorizazioa ikertu da.Mikrokapsularatze-prozesuan lortutako aurrerapenek mugarri esanguratsu bat adierazten dute ingurumen-osasunean dauden ingurumen-arazoak ebazteko.Hitz gakoak: ingurumen-osasuna, mikrokapsularatzea, askapena.EKAIA 32.indd 67 EKAIA 32.indd 67

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“…Among the photoprotection strategies available for active substances, the formulation of drug-cyclodextrin inclusion complexes has proven to be a very promising alternative [2][3][4]. Cyclodextrins (CD) are oligosaccharides derived from starch, comprising units of -D-glucopyranose joined by , 1-4 bonds, with a structure similar to a truncated cone.…”

Section: Introductionmentioning

confidence: 99%

“…Due to their low toxicity, availability, and accessible costs, cyclodextrins are being used more and more frequently, especially in drug photoprotection studies. Several studies have shown a significant reduction in photodegradation in inclusion complexes of cyclodextrins containing methotrexate [3], quercetin [4], isradipine [6], ibuprofen [7], and some dihydropyridines [8,9].…”

Section: Introductionmentioning

confidence: 99%

Photostability of Loratadine Inclusion Complexes with Natural Cyclodextrins

Rivas-Granizo¹,

Giorgetti²,

Ferraz

2015

International Journal of Photoenergy

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The purpose of this study was to evaluate the photostability of inclusion complexes of the histamine antagonist loratadine (LORA) withα-,β-, andγ-cyclodextrins (CDs). Accordingly, binary drug-CD complexes were prepared using the coevaporation method at 1 : 1, 1 : 2, and 1 : 3 stoichiometric ratios, which were characterized by thermal analysis. Subsequently, solutions of the complexes at 500 μg mL−1in HCl 0.1 M were subjected to irradiation in a photostability chamber for 12 hours, and the content of the remaining active ingredient was quantified by means of high-performance liquid chromatography. It is possible to observe the presence of two products originating from photodegradation (P1 and P2), which were identified in solutions of loratadine withα- andβ-CD. By means of statistical analysis, we conclude that the drug:α-CD and drug:γ-CD (1 : 1) complexes proved to be more efficient in the photostability assay, obtaining a nonsignificant level of degradation and full recovery of LORA.

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Evaluation of the photoprotective effect of β-cyclodextrin on the emission of volatile degradation products of ranitidine

Cited by 13 publications

References 18 publications

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

Bioziden mikrokapsulazioa eta ingurumen-osasuna

Photostability of Loratadine Inclusion Complexes with Natural Cyclodextrins

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