The crystal structure of sulfamethoxazole, interaction with DNA, DFT calculation, and molecular docking studies

Das, Dipankar; Sahu, Nilima; Roy, Suman; Dutta, Paramita; Mondal, Sudipa; Torres, Elena L.; Sinha, Chittaranjan

doi:10.1016/j.saa.2014.08.034

Cited by 23 publications

(13 citation statements)

References 38 publications

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“…respectively, which matched well with the N-N bond lengths reported in the literature[35,51]. The bonding strength between azo-N(4) and acetyl acetone (C(17)-N(4), 1.319(3) Å) is stronger than that of azo-N(3) and sulfonamide-phenyl-C(11) (C(11)-N(3), 1.412(3) Å).…”

supporting

confidence: 87%

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Structures, antimicrobial activity, DNA interaction and molecular docking studies of sulfamethoxazolyl-azo-acetylacetone and its nickel(II) complex

et al. 2015

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supporting

confidence: 87%

“…The drug likeness of the ligand has been checked following Lipinski's rule of five [35]. ADMET modules of discovery studio client 4.0 have been used to check the ADMET (absorption, distribution, metabolism, excretion and toxicity) properties of the compounds.…”

Section: Molecular Docking Studies Of the Ligand With Dhps In The Prementioning

confidence: 99%

Structures, antimicrobial activity, DNA interaction and molecular docking studies of sulfamethoxazolyl-azo-acetylacetone and its nickel(II) complex

et al. 2015

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“…Bağ uzunluğundaki bu sapmalardan dolayı bağ açısındaki en büyük sapmalar da C4-S1-N2 ve O1-S1-O2 bağ açılarında sırasıyla 4.46° ve 2.80° olduğu görülmektedir. Literatürle karşılaştırıldığında en büyük sapmaların yine N-S bağ uzunluklarında ve C-S-N bağ açılarında olduğu görülmüştür [21]. Geometrik parametrelerin teorik değerleri, küçük farklılıklara rağmen neredeyse deneysel değerlerle uyumludur (Şekil 6).…”

Section: Tablo 3 Kompleksin Hidrojen Bağ Geometrisi D-h•••unclassified

Sülfametiyazol-2,2′-Bipiridin Tuzunun Yapısal ve Spektral İncelenmesi: Deneysel ve Moleküler Modelleme Çalışması

Öztürk

Aycan

Çon

2020

Bitlis Eren Üniversitesi Fen Bilimleri Dergisi

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ÖzBu çalışmada sülfametiyazol-2,2′-bipiridin tuzunun sentezi, spektroskopik özellikleri (IR, UV-Vis ve termal) açıklanmaktadır. Birim hücrenin asimetrik biriminde, bir sülfametiyazol, bir 2,2′-bipiridin içermektedir. Karakterizasyon için tek kristal X-ışını kırınımı tekniği kullanılmıştır. 296 K' de tek kristal X-ışını kırınımı sonucuna göre P21/n monoklinik uzay grubunda a = 8.658 (3) Å, b = 24.686 (6) Å, c = 9.927 (4) Å, α = 90º, β = 103.61 (3)º, γ = 90º ve Z = 4 olarak kristallendiği görülmüştür. Molekülün FT-IR ve UV-Vis spektroskopileri teorik ve deneysel olarak karşılaştırılmıştır. Teorik hesaplamalar ve optimize edilmiş geometrik parametrelerin tümü, yoğunluk fonksiyonel teorisi (DFT), B3LYP hibrit yöntemi 6-31G (d,p) baz seti kullanılarak hesaplanmıştır. TGA ile termal özellikler incelenmiştir. Kompleksin Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, Candida albicans ve Aspergillus flavus'a karşı antimikrobiyal çalışmaları yapılmıştır. Optimize edilmiş kompleks, 5J9B, 5BMM, 5HTG, 1ZUV, 4F0V ve 4YNU'ya yerleştirilerek biyolojik aktivitesi teorik olarak incelenmiştir.

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“…In the last decades, many N4-and N1-substituted sulfonamides have been widely investigated due to their bacteriostatic activity against human and veterinary pathogens [12,13]. Previous studies of crystal polymorphism in sulfonamides have been reported in experimental investigations [9,[14][15][16] and theoretical approaches [9,17].…”

Section: Introductionmentioning

confidence: 99%

“…The bacteriostatic activity of the arylsulfonamides is their biomimetism with the p-aminobenzoic acid in the folic acid metabolism path. In addition to their antimicrobial use, the sulfonamides have also many therapeutic applications as antifungal, antidiabetic, antiglaucoma, antiallergic, antiobesity, vasodilator, anti-HIV, and anticancer [ 9 , 10 ]. In previous works we showed that the substitution of groups in the SO 2 N1H moiety for one of the H atoms on N1 may influence the tendency of the second H atom to participate in hydrogen bonding, that is, this region is an important interaction site.…”

Section: Introductionmentioning

confidence: 99%

Crystal polymorphism and spectroscopical properties of sulfonamides in solid state by means of First Principles calculations

Sainz‐Díaz

Luz

Barrientos-Salcedo

et al. 2022

J Comput Aided Mol Des

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Sulfonamides are an important class of therapeutic agents. The increase in the number of new sulfonamide derivatives makes it necessary to study more rationally the chemical structure, because the solid forms often display different mechanical, thermal and physicochemical properties that can influence the bioavailability and stability of the drugs; consequently, the polymorphic structures are of great interest to the pharmaceutical industry because of their ability to modify the physical properties of the active pharmaceutical ingredient. The molecular interactions of these drugs in their crystal lattice are important for the stability of the crystals and polymorphism and for preparing composite complexes for optimizing the use of these drugs. In this work, the crystal structure of these drugs and crystal polymorphism is investigated. So, the crystal forms of antibiotics derivatives of the sulfonamides, sulfamethoxazole, sulfamethazine, sulfachloropyridazine, and sulfacetamide are studied at the molecular and supramolecular level by using computational modeling approach at quantum mechanical level. The spectroscopic properties of these systems are also studied explaining assignments of previous experimental data. The results of DFT calculations reproduce the crystal structures of sulfonamides determined experimentally and the polymorphism in these molecules have been clarified. Likewise, the main intermolecular interactions in all crystal forms of these sulfonamides are H-bonds among the sulfonic and amino groups and SNH groups, and also some π-π interactions. Also, these 3-D periodical models allow the exploration of the intermolecular interactions included in the crystal structures and some of these interactions can alter the vibration modes of the molecules. Therefore, the use of these models can be useful for experimental spectroscopy studies where use actual crystal solids.

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The crystal structure of sulfamethoxazole, interaction with DNA, DFT calculation, and molecular docking studies

Cited by 23 publications

References 38 publications

Structures, antimicrobial activity, DNA interaction and molecular docking studies of sulfamethoxazolyl-azo-acetylacetone and its nickel(II) complex

Structures, antimicrobial activity, DNA interaction and molecular docking studies of sulfamethoxazolyl-azo-acetylacetone and its nickel(II) complex

Sülfametiyazol-2,2′-Bipiridin Tuzunun Yapısal ve Spektral İncelenmesi: Deneysel ve Moleküler Modelleme Çalışması

Crystal polymorphism and spectroscopical properties of sulfonamides in solid state by means of First Principles calculations

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