Aggregation phenomena of cinchonine in aqueous solutions observed and analysed by 2D FT-Raman spectroscopy

Wesełucha–Birczyńska, Aleksandra

doi:10.1016/j.vibspec.2004.01.011

Cited by 11 publications

(6 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…, Table S3 (Supporting Information)). Our findings are in good agreement with some results already reported in literature …”

Section: Resultssupporting

confidence: 94%

“…Our findings are in good agreement with some results already reported in literature. [20,56,57] FT-IR spectra show some similarities in pairs QN-QND and CN-CND; however, in case of the second pair, these similarities are much more distinct. The most intense band in FT-IR spectrum of QN is observed at 1239 cm À1 and comes from stretching and deformation vibrations localized mostly in the quinoline ring system (Table S3 (Supporting Information)).…”

Section: Conformational Analysismentioning

confidence: 97%

See 1 more Smart Citation

Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

Roman

Chruszcz‐Lipska

Barańska

2015

J Raman Spectroscopy

View full text Add to dashboard Cite

Cinchona alkaloids are well-known antimalarial compounds also used in asymmetric synthesis in organic chemistry. In this work, vibrational spectra of quinine, quinidine, cinchonine, and cinchonidine were acquired and interpreted on the basis of theoretical calculations. Normal Raman spectra of the alkaloids in solution exhibit similar patterns and cannot be used for differentiation between the derivatives (e.g. quinine and cinchonidine) and corresponding pseudoenantiomers (e.g. quinine and quinidine). Thus, Raman Optical Activity (ROA) method was applied to show distinct differences related to the configuration of chiral atoms. ROA allowed unequivocal identification of the pseudoenantiomers based on the sign of the characteristic bands from a single measurement. The experiments were supported by the theoretical approach including conformational study followed by wavenumber calculations and Potential Energy Distribution (PED) analysis. For quinine, vibrational spectroscopy was additionally used to show its structural changes in aqueous solutions at various pH and its distribution in a pharmaceutical product. Spatial distribution of quinine in a drug was observed by the FT-Raman mapping technique.

show abstract

“…, Table S3 (Supporting Information)). Our findings are in good agreement with some results already reported in literature …”

Section: Resultssupporting

confidence: 94%

Section: Conformational Analysismentioning

confidence: 97%

Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

Roman

Chruszcz‐Lipska

Barańska

2015

J Raman Spectroscopy

View full text Add to dashboard Cite

show abstract

“…Two‐dimensional correlation spectroscopy has also been used to examine pH73 and aggregation74 effects of Cinchona alkaloids used in antimalarial treatment and pH structural changes of (hydroxypyridin‐3‐yl‐methyl)phosphonic acid, a model compound of risedronate which is an agent used in osteoporosis treatment 75…”

Section: Raman Spectroscopymentioning

confidence: 99%

Recent pharmaceutical applications of raman and terahertz spectroscopies

McGoverin

Rades

Gordon

2008

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

“…These alkaloids belong to a broad group of natural heterocyclic compounds containing nitrogen. Cinchonine is a weak base and crosses the pH gradient of red blood cells to accumulate in the acid vacuoles of the parasites, an important mechanism in its antimalarial action ( Weselucha-Birczynska, 2004 ). Furthermore, the metal coordination with pre-existing antimalarials and bio-organometallic compounds has shown promising efficacy during in vitro experiments against chloroquine-sensitive and resistant P. falciparum strains ( Salas et al., 2013 ).…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, the metal coordination with pre-existing antimalarials and bio-organometallic compounds has shown promising efficacy during in vitro experiments against chloroquine-sensitive and resistant P. falciparum strains ( Salas et al., 2013 ). Copper can be coordinated with several ligands, including cinchonine, and exhibits antiviral activity, treats inflammatory diseases, and microbial infections, and has antimalarial activity ( Gokhale et al., 2003 ; Weselucha-Birczynska, 2004 ; Mohapatra et al., 2010 ; Stanila et al., 2011 ).…”

Section: Introductionmentioning

confidence: 99%

Blood-stage antiplasmodial activity and oocyst formation-blockage of metallo copper-cinchonine complex

Morais

Brito

Wesełucha–Birczyńska

et al. 2022

Front. Cell. Infect. Microbiol.

View full text Add to dashboard Cite

In the fight against malaria, the key is early treatment with antimalarial chemotherapy, such as artemisinin-based combination treatments (ACTs). However, Plasmodium has acquired multidrug resistance, including the emergence of P. falciparum strains with resistance to ACT. The development of novel antimalarial molecules, that are capable of interfering in the asexual and sexual blood stages, is important to slow down the transmission in endemic areas. In this work, we studied the ability of the mettalo copper-cinchonine complex to interfere in the sexual and asexual stages of Plasmodium. The tested compound in the in vitro assay was a cinchonine derivative, named CinCu (Bis[Cinchoninium Tetrachlorocuprate(II)]trihydrate). Its biological functions were assessed by antiplasmodial activity in vitro against chloroquine-resistant P. falciparum W2 strain. The mice model of P. berghei ANKA infection was used to analyze the antimalarial activity of CinCu and chloroquine and their acute toxicity. The oocyst formation-blocking assay was performed by experimental infection of Anopheles aquasalis with P. vivax infected blood, which was treated with different concentrations of CinCu, cinchonine, and primaquine. We found that CinCu was able to suppress as high as 81.58% of parasitemia in vitro, being considered a molecule with high antiplasmodial activity and low toxicity. The in vivo analysis showed that CinCu suppressed parasitemia at 34% up to 87.19%, being a partially active molecule against the blood-stage forms of P. berghei ANKA, without inducing severe clinical signs in the treated groups. The transmission-blocking assay revealed that both cinchonine and primaquine were able to reduce the infection intensity of P. vivax in A. aquasalis, leading to a decrease in the number of oocysts recovered from the mosquitoes’ midgut. Regarding the effect of CinCu, the copper-complex was not able to induce inhibition of P. vivax infection; however, it was able to induce an important reduction in the intensity of oocyst formation by about 2.4 times. It is plausible that the metallo-compound also be able to interfere with the differentiation of parasite stages and/or ookinete-secreted chitinase into the peritrophic matrix of mosquitoes, promoting a reduction in the number of oocysts formed. Taken together, the results suggest that this compound is promising as a prototype for the development of new antimalarial drugs. Furthermore, our study can draw a new pathway for repositioning already-known antimalarial drugs by editing their chemical structure to improve the antimalarial activity against the asexual and sexual stages of the parasite.

show abstract

Aggregation phenomena of cinchonine in aqueous solutions observed and analysed by 2D FT-Raman spectroscopy

Cited by 11 publications

References 14 publications

Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions

Recent pharmaceutical applications of raman and terahertz spectroscopies

Blood-stage antiplasmodial activity and oocyst formation-blockage of metallo copper-cinchonine complex

Contact Info

Product

Resources

About