Prediction of photosensitivity of 1,4-dihydropyridine antihypertensives by quantitative structure-property relationship

Ioele, Giuseppina; Luca, Michele De; Oliverio, Filomena; Ragno, Gaetano

doi:10.1016/j.talanta.2009.06.009

Cited by 34 publications

(24 citation statements)

References 50 publications

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“…Gradual decreases of absorbance signals of the DHP chromophoric group were observed in regions 340-400 and 230-250 nm. Simultaneous appearance and increase of a new peak in region 260-310 nm was observed, which was due to the formation of the pyridine group, in agreement with our previous studies (14)(15)(16). The sequence of the recorded spectra for all studied compounds evidenced the formation of photodegradation products.…”

Section: Photostability Studysupporting

confidence: 90%

“…In our previous studies (14)(15)(16)(30)(31)(32), the infl uence of sample concentration on the photodegradation profi le was demonstrated. However, in this study, degradation kinetics and the number of photoproducts remained unchanged with increasing concentration of analytes.…”

Section: Photostability Studymentioning

confidence: 93%

“…Several reports evidence the photolability of DHPs used in therapy (15)(16)(17)(18). Photodegradation tests of the newly synthesized compounds were performed with the aim to identify DHP structures more photostable than the currently known congeners.…”

Section: Photostability Studymentioning

confidence: 99%

“…Formation of a single photoproduct (P1), corresponding to the pyridine derivative according to the literature (14)(15)(16)(17)(18), was calculated for all the studied compounds. Only compound DHP4 showed diff erent behavior with the probable formation of the fi rst degradation product (P1), followed by a secondary photoproduct (P2), as indicated by the number of species involved in the kinetic process, obtained by SVD data elaboration, and by the presence of two k values.…”

Section: Photostability Studymentioning

confidence: 99%

“…The muscle relaxant activity of these compounds was evaluated on isolated rabbit gastric fundus smooth muscle strips and compared to that of NIF. Due to the well-known photo-lability of DHPs (15)(16)(17)(18), the synthesized compounds were subjected to photodegradation tests (19). Concentration of parent compounds and by-products was calculated by multivariate curve resolution-alternating least squares (MCR-ALS) applied to the spectral data (20)(21)(22).…”

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confidence: 99%

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Synthesis and photodegradation studies of analogues of muscle relaxant 1,4-dihydropyridine compounds

et al. 2017

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This paper describes the synthesis of 1,4-dihydropyridine compounds (DHPs) endowed with good muscle relaxant activity and stability to light. Six new condensed DHPs were synthesized by the microwave irradiation method. A long-chain ester moiety [2-(methacryloyloxy)ethyl] and various substituents on the phenyl ring were demonstrated to aff ect the muscle relaxant activity occurring in isolated rabbit gastric fundus smooth muscle strips. Forced photodegradation conditions were applied to the molecules according to the ICH rules. The degradation profi le of the drugs was monitored by spectrophotometry coupled with the multivariate curve resolution technique. Formation of the oxidized pyridine derivative was observed for all the studied DHPs, except for one compound, which showed very fast degradation and formation of a second photoproduct. Pharmacological tests on the molecules showed a good muscle relaxing eff ect, with a mechanism similar to that of nifedipine, however, proving to be more stable to light.

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Section: Photostability Studysupporting

confidence: 90%

Section: Photostability Studymentioning

confidence: 93%

Section: Photostability Studymentioning

confidence: 99%

Section: Photostability Studymentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis and photodegradation studies of analogues of muscle relaxant 1,4-dihydropyridine compounds

et al. 2017

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Quantitative structure property relationships to evaluate the photosensitizing capability in porphyrins and chlorins

Cárdenas-Jirón

Santander-Nelli

López

et al. 2011

Int J of Quantum Chemistry

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ABSTRACT:The wavelength of the Q band (k Q ) of sixteen compounds (porphyrins and chlorins) was related to eight descriptors (aromatic, electrostatic, and reactivity ones) by using quantitative structure property relationships (QSPR). These descriptors were calculated using density functional theory (DFT). No single linear regressions were found. So, our work demonstrates that k Q does not depend on a unique property; rather it is a multidimensional parameter. From twelve QSPR models obtained, four of them yielded regression coefficients over 0.8. In addition, the k Q values resulting from our QSPR models are closer to experiment than time dependent-DFT calculated ones. It has been proved the power of QSPR models to reproduce and predict the k Q values for new porphyrin derivatives with potential capability to be used in Photodynamic Therapy.

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Regiospecific Reduction of the C=N Bond in 5,6-Dialkyl-2-Chloropyridine-3,4-Dicarbonitriles

Ершов

Belikov

Максимова

et al. 2014

Chem Heterocycl Comp

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Prediction of photosensitivity of 1,4-dihydropyridine antihypertensives by quantitative structure-property relationship

Cited by 34 publications

References 50 publications

Synthesis and photodegradation studies of analogues of muscle relaxant 1,4-dihydropyridine compounds

Synthesis and photodegradation studies of analogues of muscle relaxant 1,4-dihydropyridine compounds

Quantitative structure property relationships to evaluate the photosensitizing capability in porphyrins and chlorins

Regiospecific Reduction of the C=N Bond in 5,6-Dialkyl-2-Chloropyridine-3,4-Dicarbonitriles

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