Design and synthesis of novel hydroxyalkylaminomethylchromones for their IL-5 inhibitory activity

Pillaiyar, Thanigaimalai; Lee, Ki-Cheul; Sharma, Vinay K.; Yun, Juyoung; Kim, Youngsoo; Jung, Sang‐Hun

doi:10.1016/j.bmc.2010.05.028

Cited by 16 publications

(10 citation statements)

References 15 publications

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“…Chromones and their structural analogs are of great interest because of their usefulness as biologically active agents. They have been shown to be tyrosine and protein kinase inhibitors, as well as anticancer [27–30], neuroprotective [31], anti-AIDS [32–34], antimicrobial [35,36], antifungal [37], antioxidant activity [38], interleukin-5 inhibitory activity [39], and antiproliferative agents [40]. Chromones may also have application in cystic fibrosis treatment, as they activate the cystic fibrosis transmembrane conductance regulator.…”

Section: Introductionmentioning

confidence: 99%

Physiochemical, Optical and Biological Activity of Chitosan-Chromone Derivative for Biomedical Applications

Kumar

Koh

2012

IJMS

355

133

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This paper describes the physiochemical, optical and biological activity of chitosan-chromone derivative. The chitosan-chromone derivative gels were prepared by reacting chitosan with chromone-3-carbaldehyde, followed by solvent exchange, filtration and drying by evaporation. The identity of Schiff base was confirmed by UV-Vis absorption spectroscopy and Fourier-transform infrared (FTIR) spectroscopy. The chitosan-chromone derivative was evaluated by X-ray diffraction (XRD), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), scanning electron microscopy (SEM), photoluminescence (PL) and circular dichroism (CD). The CD spectrum showed the chitosan-chromone derivative had a secondary helical structure. Microbiological screening results demonstrated the chitosan-chromone derivative had antimicrobial activity against Escherichia coli bacteria. The chitosan-chromone derivative did not have any adverse effect on the cellular proliferation of mouse embryonic fibroblasts (MEF) and did not lead to cellular toxicity in MEFs. These results suggest that the chitosan-chromone derivative gels may open a new perspective in biomedical applications.

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Section: Introductionmentioning

confidence: 99%

Physiochemical, Optical and Biological Activity of Chitosan-Chromone Derivative for Biomedical Applications

Kumar

Koh

2012

IJMS

355

133

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“…Compound 1 presents very low CMR value, whereas compound 16 presents the highest CMR value. Equation (15) does not contain a π or ClogP term. However, ClogP vs. MgVol=0.532.…”

Section: Sar and Qsar In Environmental Research 919mentioning

confidence: 97%

“…In 2010 Jung et al [15] prepared a series of novel hydroxyalkylaminomethylchromones in order to investigate thoroughly their structure-activity relationships and to evaluate their ability to inhibit interleukin-5.The IC 50 data values ( Table 2) led to the following equation (Equation 6): MgVol is the calculated McGowan's volume and its positive coefficient indicates that steric factors are important for the interaction with the receptor. Although Equation (2) is not sharp in terms of r 2 , it is statistically significant.…”

Section: Hydroxyalkylaminomethylchromonesmentioning

confidence: 99%

“…Structures, biological data [30] and physiochemical parameters used to obtain Equation (15). Clog P vs: I T ¼ 0:209; Clog P vs: I F ¼ 0:000; I T vs:…”

Section: -Amino-3-heteroaryl-quinoxalinesmentioning

confidence: 99%

“…Although corticosteroids are established immunosuppressive agents, their action is not selective and they cause metabolic and endocrinal side effects [9], whereas compounds with IL-5 inhibitory activity act selectively in reducing eosinophilic inflammation. In the literature small molecules are referred as IL-5 inhibitors (Figure 1): chalcones [10,11], isothiazolones through modification of Cys66 (Cysteine66) in IL-5Ra (interleukin 5 receptor subunit alpha) [12], isoflavonones as sophoricoside analogues [13,14], hydroxyalkylaminomethylchromones [15], derivatives based on hydroxyethylaminomethyl-4H-chromen-4-one scaffold [16], chromone analogues [17], isoflavones and aurones [18]. Mepolizumab and reslizumab, two monoclonal anti-IL-5 antibodies, and benralizumab, a monoclonal antibody directed at the IL-5 receptor, have been tested in clinical trials for the treatment of bronchial asthma, nasal polyposis, atopic dermatitis, eosinophilic oesophagitis, hypereosinophilic syndrome and Churg-Strauss syndrome [19].…”

Section: Introductionmentioning

confidence: 99%

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Cytokines in terms of QSAR. Review, evaluation and comparative studies

Konstantinidou

Hadjipavlou‐Litina

2013

SAR and QSAR in Environmental Research

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Cytokines represent a class of chemical factors that act as mediators in the complex biological response of inflammation, potentially implicated in various diseases. Therefore, selective inhibition or antagonism of cytokines is a target of anti-inflammatory drug design. The QSAR (Quantitative Structure-Activity Relationships) analysis presented here attempts to identify the structural features and physicochemical properties that are significant for cytokine antagonists or inhibitors and in particular of i) interleukin-5 (IL-5), ii) interleukin-6 (IL-6) and iii) of the chemotactic cytokine (chemokine) interleukin-8 (IL-8). Firstly, a historical aspect of the limited published QSARs is discussed and then a 2D-QSAR analysis was carried out for 26 data sets of compounds using the C-QSAR program of Biobyte. In six cases hydrophobicity appeared to be important. Steric factors in the form of overall molar refractivity (CMR), molar refractivity of the substituent (MR), molar volume (MgVol), Taft's Es constant and the sterimol parameters B1 and B5 have a significant impact on biological activity in most of the derived equations whereas electronic parameters as σp, σm or Σσ appeared in five cases.

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Synthesis and Biological Evaluation of New Bischromone Derivatives with Antiproliferative Activity

Szulawska-Mroczek

Szumilak

Szczesio

et al. 2012

Archiv der Pharmazie

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The synthesis of new bischromone derivatives (4a-c and 5a-c) as potential anticancer drugs is described. The difference in the reactivity between 4-oxo-4H-chromene-3-carboxylic acid 2 (or its methyl ester 3) and 4-oxo-4H-chromene-3-carbonyl chloride 1 with three different polyamines: 3,3'-diamino-N-methyldipropylamine (a), 1,4-bis(3-aminopropyl)piperazine (b), 4,9-dioxa-1,12-dodecanediamine (c) resulted in the formation of two different groups of products, compounds 4a-c and 5a-c, designed in agreement with the bisintercalators' structural requirements. The transformation of 4-oxo-4H-chromene-3-carboxylic acid into 2H-chromene-2,4(3H)-diones (5) was confirmed by the NMR and XRD experiments. Compounds 4a and 5a were evaluated in vitro in the highly aggressive melanoma cell line A375. An enhanced induction of apoptosis and cell cycle arrest clearly revealed that compound 5a was more potent than 4a. Compound 5a was also more active in diminishing the adhesive potential of melanoma cells. Current studies support the notion that small changes in the three-dimensional structure of molecules might have a substantial impact on their biological activity.

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Design and synthesis of novel hydroxyalkylaminomethylchromones for their IL-5 inhibitory activity

Cited by 16 publications

References 15 publications

Physiochemical, Optical and Biological Activity of Chitosan-Chromone Derivative for Biomedical Applications

Physiochemical, Optical and Biological Activity of Chitosan-Chromone Derivative for Biomedical Applications

Cytokines in terms of QSAR. Review, evaluation and comparative studies

Synthesis and Biological Evaluation of New Bischromone Derivatives with Antiproliferative Activity

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