Synthesis, spectroscopic characterizations, carbonic anhydrase II inhibitory activity, anticancer activity and docking studies of new Schiff bases of sulfa drugs

Alyar, Saliha; Özmen, Ümmühan Özdemir; Adem, Şevki; Alyar, Hamit; Bilen, Esra; Kaya, Kerem

doi:10.1016/j.molstruc.2020.128911

Cited by 46 publications

(10 citation statements)

References 56 publications

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“…The 100 ml of pure water, the 80 μL of 100 mM Tris-SO4 buffer (pH: 8.0), the 80 μl of 3 mM 4-nitrophenyl acetate, and 20 μL enzyme were added to the reaction mix for human CA isoenzymes (hCAI and hCAII). [27] For porcine PCE activity assay, the reaction mixture was created by adding 80 μl of 100 mM phosphate buffer (pH:7) containing 100 mM NaCl, 100 μl of 12 mM NAT, 20 μl of 20 mM p-nitrophenyl butyrate at assay buffer, 80 μL of pure water and 10 μL enzyme [28,29] For inhibition studies, the compound was dissolved as 1 mg/ml at DMSO, and then diluted 10 times with distilled water to use as a stock solution. Enzyme activities were assayed at the different inhibitory concentrations by reducing the amount of water as much as the inhibitor volume.…”

Section: Enzyme Studiesmentioning

confidence: 99%

Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies

Hamurcu,

Özmen,

Şentürk

et al. 2023

Chemistry & Biodiversity

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A novel Schiff base namely 3,5‐di‐tert‐butyl‐6‐((2‐(perfluorophenyl) hydrazono) methyl) phenol was successfully synthesized and characterized using FTIR and 1H‐NMR, 13C‐NMR, and 19F‐NMR. The crystal structure analysis of the Schiff base compound was also characterized with single crystal X‐ray diffraction studies and supported the spectroscopic results. The cytotoxicity, anti‐bacterial properties, and enzyme inhibition of the compound were also investigated. The molecular docking studies were performed in order to explain the interactions of the synthesized compound with target enzymes. The newly synthesized hydrazone derivative Schiff base compound showed high cellular toxicity on MCF‐7 and PC‐3 cells. Also, this compound caused low antibacterial effect on E. coli and S. aureus. Besides, the compound exhibited the inhibitory effect against pancreatic cholesterol esterase and carbonic anhydrase isoenzyme I, II with IC50 values 63, 99, and 188 µM, respectively. Consequently, it has been determined that the prepared Schiff base is an active compound in terms of cytotoxicity, enzyme inhibition, and anti‐bacterial properties. These results provide preliminary information for some biological features of the compound and can play a major role in drug applications of the Schiff base compound.

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Section: Enzyme Studiesmentioning

confidence: 99%

Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies

Hamurcu,

Özmen,

Şentürk

et al. 2023

Chemistry & Biodiversity

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“…These effects were markedly enhanced on the combination of Schiff base and cisplatin. Alyar et al (2021) [48] reported the synthesis and biological evaluation of new Schiff bases incorporating sulfisoxazole and sulfamethoxazole and their Cu(II) complexes. The anticancer activity was evaluated against three human cancer cell lines with the sulfonamide B test.…”

Section: Antiproliferative Activity Of Schiff Bases Complexed With Transition Metalsmentioning

confidence: 99%

“…Sci. 2021, 11, x FOR PEER REVIEW 7 of -S1)2 (12) IC50 = 40 µ M (MCF-7) Alyar et al (2021) [48] Cu(S2M-S1) 2 (11) IC 50 = 40 µM (MCF-7) Alyar et al (2021)[48]…”

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confidence: 99%

A Review on the Advancements in the Field of Metal Complexes with Schiff Bases as Antiproliferative Agents

et al. 2021

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Metal complexes play an essential role in pharmaceutical sciences for their multiple and important activities. Schiff bases are versatile pharmacophores able to form chelating complexes with several metals in different oxidation states. Complexes with Schiff bases are widely described in the literature for their multiple actions and numerous advantages, such as low cost and easy synthesis. They show multiple biological activities, including antimicrobial, antioxidant, antimalarial, antinflammatory and antitumor. Schiff bases may also form complexes with lanthanides and actinides acting as catalysts (e.g., in various synthetic processes) and antitumor agents. This review intends to extend on our previous paper regarding Schiff bases as antitumorals, highlighting the importance, in the field of the anticancer agents, of these tools as ligands of metal complexes.

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“…[9] Schiff bases are a signi cant class of organic and bioinorganic compounds because they have substantial pharmacological activities such as cytotoxicity, DNA cleavages, antifungal, antibacterial, antimalarial, antiproliferative, anti-in ammatory, antiviral, antioxidant, anticancer, analgesic, antipyretic, antidiabetic and anti-HIV activities. [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24] Schiff bases containing heterocycles have drawn much attention due to their diverse biological activity. [25] Extra hydroxyl group at ortho and para position with respect to imines linkage increases antifungal activity against C.albicans fungi.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal structure, in vitro, and in silico biological studies of 2, 5-dihydroxybenzaldehyde based novel Schiff bases

Todarwal

Sancheti

Shah

et al. 2023

Preprint

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The present study reports the synthesis of novel Schiff base ligands (S1-S8) derived from 2, 5-dihydroxybenzaldehyde by coupling with substituted amines. Further, the electron-donating and electron-withdrawing substituents on the amines are intended to tune the properties of the new Schiff base ligands. The chemical structures of these compounds were extensively elucidated by FT-IR, 1H-NMR, 13C-NMR, and ESI-MS. The X-ray analyses show that the compounds crystallized in a triclinic crystal system with a space group of P-1 and Z = 2 for S1. Besides, antimicrobial potency against gram-positive bacteria and gram-negative bacteria, as well as against fungi, was studied. S3 has superior inhibitory activity against all bacterial strains. The consortium of different substituent atoms on the phenyl ring and the heterocyclic ring counterpart is one of the reasons behind the recorded optimal activity. Compound S8 has potent antifungal inhibitory action against C.albicans compared to the standard antifungal, whereas Schiff base S5 also has well to moderate activity against all fungal strains. A molecular docking result indicates that these compounds could also be effective against the resistance β-ketoacyl-ACP (acyl carrier protein) synthase-I enzyme of E.coli.

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Synthesis, spectroscopic characterizations, carbonic anhydrase II inhibitory activity, anticancer activity and docking studies of new Schiff bases of sulfa drugs

Cited by 46 publications

References 56 publications

Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies

Biological Effects and Crystal X‐Ray Study of Novel Schiff Base Containing Pentafluorophenyl Hydrazine: In Vitro and in Silico Studies

A Review on the Advancements in the Field of Metal Complexes with Schiff Bases as Antiproliferative Agents

Synthesis, Crystal structure, in vitro, and in silico biological studies of 2, 5-dihydroxybenzaldehyde based novel Schiff bases

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