Synthesis, spectroscopic characterization, thermal analysis and in vitro bioactivity studies of the N-(cinnamylidene) tryptophan Schiff base
The objective of this study was to investigate the bioactivity of N-(cinnamylidene) tryptophan (CinTrp), including its in vitro hemolytic effect on erythrocytes, at different concentrations (20–1000 µg/mL). CinTrp was synthesized by condensing cinnamaldehyde (Cin) and tryptophan (Trp) in a basic med...
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| Format: | Article |
| Language: | English |
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Elsevier
2022-06-01
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| Series: | Journal of King Saud University: Science |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1018364722001690 |
| _version_ | 1828810253277331456 |
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| author | Mohammed Mansour S. Saif Riad M. Alodeni Abdulaziz Ali Alghamdi Abdel-Basit Al-Odayni |
| author_facet | Mohammed Mansour S. Saif Riad M. Alodeni Abdulaziz Ali Alghamdi Abdel-Basit Al-Odayni |
| author_sort | Mohammed Mansour S. Saif |
| collection | DOAJ |
| description | The objective of this study was to investigate the bioactivity of N-(cinnamylidene) tryptophan (CinTrp), including its in vitro hemolytic effect on erythrocytes, at different concentrations (20–1000 µg/mL). CinTrp was synthesized by condensing cinnamaldehyde (Cin) and tryptophan (Trp) in a basic medium. Its physicochemical, spectral, and thermal properties were analyzed using Fourier transform infrared, proton and 13-carbon nuclear magnetic resonance, electronic, and mass spectroscopy, as well as thermogravimetric and differential scanning calorimetry. Antibacterial activity against Gram-positive (S. aureus) and Gram-negative (E. coli, P. aeruginosa, and K. pneumoniae) bacteria was assessed using the agar disk-diffusion method, while the hemolytic effect on human erythrocytes was spectrophotometrically determined. Thermal analysis suggested that CinTrp is less stable than its Trp precursor. The antibacterial activity of CinTrp against E. coli was close to that of ceftriaxone, while against K. pneumoniae it was nearly half that for ampicillin and ceftriaxone standard drugs. No effects on S. aureus and P. aeruginosa were observed. Cell hemolysis test in reference to phosphate-buffered saline (negative) and Triton X-100 (0.1% v/v) (positive) controls indicated low or no effects up to 250 µg/mL (≤1.50% ± 3.06%), with a slight increase up to 750 µg/mL (6.50% ± 2.87%); however, lysis of 23.13% ± 7.76% at 1000 µg/mL was detected. It could be concluded that CinTrp is more active against Gram-negative bacteria and its hemolytic effect on erythrocytes apparently begins above 250 µg/mL. However, additional analyses in terms of the concentration range, methods, and types of microorganisms may be necessary to assuage safety concerns and deepen understanding. |
| first_indexed | 2024-12-12T09:09:10Z |
| format | Article |
| id | doaj.art-713d026429414297a532fe4260cfc540 |
| institution | Directory Open Access Journal |
| issn | 1018-3647 |
| language | English |
| last_indexed | 2024-12-12T09:09:10Z |
| publishDate | 2022-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of King Saud University: Science |
| spelling | doaj.art-713d026429414297a532fe4260cfc5402022-12-22T00:29:34ZengElsevierJournal of King Saud University: Science1018-36472022-06-01344101988Synthesis, spectroscopic characterization, thermal analysis and in vitro bioactivity studies of the N-(cinnamylidene) tryptophan Schiff baseMohammed Mansour S. Saif0Riad M. Alodeni1Abdulaziz Ali Alghamdi2Abdel-Basit Al-Odayni3Division of Biochemistry, Chemistry Department, Faculty of Science, Ibb University, Ibb, YemenDivision of Biochemistry, Chemistry Department, Faculty of Science, Ibb University, Ibb, YemenChemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaEngineer Abdullah Bugshan Research Chair for Dental and Oral Rehabilitation, College of Dentistry, King Saud University, Riyadh 11545, Saudi Arabia; Corresponding author.The objective of this study was to investigate the bioactivity of N-(cinnamylidene) tryptophan (CinTrp), including its in vitro hemolytic effect on erythrocytes, at different concentrations (20–1000 µg/mL). CinTrp was synthesized by condensing cinnamaldehyde (Cin) and tryptophan (Trp) in a basic medium. Its physicochemical, spectral, and thermal properties were analyzed using Fourier transform infrared, proton and 13-carbon nuclear magnetic resonance, electronic, and mass spectroscopy, as well as thermogravimetric and differential scanning calorimetry. Antibacterial activity against Gram-positive (S. aureus) and Gram-negative (E. coli, P. aeruginosa, and K. pneumoniae) bacteria was assessed using the agar disk-diffusion method, while the hemolytic effect on human erythrocytes was spectrophotometrically determined. Thermal analysis suggested that CinTrp is less stable than its Trp precursor. The antibacterial activity of CinTrp against E. coli was close to that of ceftriaxone, while against K. pneumoniae it was nearly half that for ampicillin and ceftriaxone standard drugs. No effects on S. aureus and P. aeruginosa were observed. Cell hemolysis test in reference to phosphate-buffered saline (negative) and Triton X-100 (0.1% v/v) (positive) controls indicated low or no effects up to 250 µg/mL (≤1.50% ± 3.06%), with a slight increase up to 750 µg/mL (6.50% ± 2.87%); however, lysis of 23.13% ± 7.76% at 1000 µg/mL was detected. It could be concluded that CinTrp is more active against Gram-negative bacteria and its hemolytic effect on erythrocytes apparently begins above 250 µg/mL. However, additional analyses in terms of the concentration range, methods, and types of microorganisms may be necessary to assuage safety concerns and deepen understanding.http://www.sciencedirect.com/science/article/pii/S1018364722001690Hemolytic activitySpectroscopic analysisCinnamaldehydeTryptophanAzomethineSchiff base |
| spellingShingle | Mohammed Mansour S. Saif Riad M. Alodeni Abdulaziz Ali Alghamdi Abdel-Basit Al-Odayni Synthesis, spectroscopic characterization, thermal analysis and in vitro bioactivity studies of the N-(cinnamylidene) tryptophan Schiff base Journal of King Saud University: Science Hemolytic activity Spectroscopic analysis Cinnamaldehyde Tryptophan Azomethine Schiff base |
| title | Synthesis, spectroscopic characterization, thermal analysis and in vitro bioactivity studies of the N-(cinnamylidene) tryptophan Schiff base |
| title_full | Synthesis, spectroscopic characterization, thermal analysis and in vitro bioactivity studies of the N-(cinnamylidene) tryptophan Schiff base |
| title_fullStr | Synthesis, spectroscopic characterization, thermal analysis and in vitro bioactivity studies of the N-(cinnamylidene) tryptophan Schiff base |
| title_full_unstemmed | Synthesis, spectroscopic characterization, thermal analysis and in vitro bioactivity studies of the N-(cinnamylidene) tryptophan Schiff base |
| title_short | Synthesis, spectroscopic characterization, thermal analysis and in vitro bioactivity studies of the N-(cinnamylidene) tryptophan Schiff base |
| title_sort | synthesis spectroscopic characterization thermal analysis and in vitro bioactivity studies of the n cinnamylidene tryptophan schiff base |
| topic | Hemolytic activity Spectroscopic analysis Cinnamaldehyde Tryptophan Azomethine Schiff base |
| url | http://www.sciencedirect.com/science/article/pii/S1018364722001690 |
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