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Potential bioactive Schiff base compounds: synthesis, characterization, X-ray structures, biological screenings and interaction with Salmon sperm DNA.

Abstract

Three Schiff base compounds ofN'-substituted benzohydrazide and sulfonohydrazide derivatives: N'-(2-hydroxy-3-methoxybenzylidene)-4-tert-butyl- benzohydrazide (1), N'-(5-bromo-2-hydroxybenzylidene)-4-tert-butylbenzohydrazide (2) and N'-(2-hydroxy-3-methoxybenzylidene)-4-methylbenzenesulfonohydrazide (3) were synthesized and characterized by elemental analysis, FT-IR, (1)H, (13)C NMR spectroscopy and single crystal analysis. The title compounds have been screened for their biological activities including, antibacterial, antifungal, antioxidant, cytotoxic, enzymatic activities as well as interaction with SS-DNA which showed remarkable activities in each area of research. The DNA binding of the compounds 1-3 with SS-DNA has been carried out with absorption spectroscopy, which reveals the binding propensity towards SS-DNA via intercalation mode of interaction. The intercalative mode of interaction is also supported by viscometric results. The synthesized compounds were also found to be effective against alkaline phosphatase enzyme. They also show significant to good antimicrobial activity against six bacterial and five fungal strains. The MIC (minimum inhibitory concentration) for antibacterial activity ranges from 1.95-500 μg/mL. Compounds 1-3 show cytotoxic activity comparable to the control. At higher conc. (100 μg/L) compound 3 shows 100% activity means that it has killed all brine shrimps. They were also found to be effective antioxidant of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) and show almost comparable antioxidant activity to that of the standard and known antioxidant, ascorbic acid.

Authors+Show Affiliations

Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23912178

Citation

Sirajuddin, Muhammad, et al. "Potential Bioactive Schiff Base Compounds: Synthesis, Characterization, X-ray Structures, Biological Screenings and Interaction With Salmon Sperm DNA." Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, vol. 116, 2013, pp. 111-21.
Sirajuddin M, Uddin N, Ali S, et al. Potential bioactive Schiff base compounds: synthesis, characterization, X-ray structures, biological screenings and interaction with Salmon sperm DNA. Spectrochim Acta A Mol Biomol Spectrosc. 2013;116:111-21.
Sirajuddin, M., Uddin, N., Ali, S., & Tahir, M. N. (2013). Potential bioactive Schiff base compounds: synthesis, characterization, X-ray structures, biological screenings and interaction with Salmon sperm DNA. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 116, 111-21. https://doi.org/10.1016/j.saa.2013.06.096
Sirajuddin M, et al. Potential Bioactive Schiff Base Compounds: Synthesis, Characterization, X-ray Structures, Biological Screenings and Interaction With Salmon Sperm DNA. Spectrochim Acta A Mol Biomol Spectrosc. 2013;116:111-21. PubMed PMID: 23912178.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Potential bioactive Schiff base compounds: synthesis, characterization, X-ray structures, biological screenings and interaction with Salmon sperm DNA. AU - Sirajuddin,Muhammad, AU - Uddin,Noor, AU - Ali,Saqib, AU - Tahir,Muhammad Nawaz, Y1 - 2013/07/16/ PY - 2013/02/11/received PY - 2013/06/24/revised PY - 2013/06/27/accepted PY - 2013/8/6/entrez PY - 2013/8/6/pubmed PY - 2014/4/17/medline KW - Antimicrobial activity KW - Antioxidant activity KW - DNA interaction KW - Enzymatic activity KW - Schiff base KW - Single crystal SP - 111 EP - 21 JF - Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy JO - Spectrochim Acta A Mol Biomol Spectrosc VL - 116 N2 - Three Schiff base compounds ofN'-substituted benzohydrazide and sulfonohydrazide derivatives: N'-(2-hydroxy-3-methoxybenzylidene)-4-tert-butyl- benzohydrazide (1), N'-(5-bromo-2-hydroxybenzylidene)-4-tert-butylbenzohydrazide (2) and N'-(2-hydroxy-3-methoxybenzylidene)-4-methylbenzenesulfonohydrazide (3) were synthesized and characterized by elemental analysis, FT-IR, (1)H, (13)C NMR spectroscopy and single crystal analysis. The title compounds have been screened for their biological activities including, antibacterial, antifungal, antioxidant, cytotoxic, enzymatic activities as well as interaction with SS-DNA which showed remarkable activities in each area of research. The DNA binding of the compounds 1-3 with SS-DNA has been carried out with absorption spectroscopy, which reveals the binding propensity towards SS-DNA via intercalation mode of interaction. The intercalative mode of interaction is also supported by viscometric results. The synthesized compounds were also found to be effective against alkaline phosphatase enzyme. They also show significant to good antimicrobial activity against six bacterial and five fungal strains. The MIC (minimum inhibitory concentration) for antibacterial activity ranges from 1.95-500 μg/mL. Compounds 1-3 show cytotoxic activity comparable to the control. At higher conc. (100 μg/L) compound 3 shows 100% activity means that it has killed all brine shrimps. They were also found to be effective antioxidant of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) and show almost comparable antioxidant activity to that of the standard and known antioxidant, ascorbic acid. SN - 1873-3557 UR - https://www.unboundmedicine.com/medline/citation/23912178/Potential_bioactive_Schiff_base_compounds:_synthesis_characterization_X_ray_structures_biological_screenings_and_interaction_with_Salmon_sperm_DNA_ DB - PRIME DP - Unbound Medicine ER -