Investigation of synthesis, characterization, photophysical and biological properties of novel antimicrobial fluorescent naphthalimide derivatives
Shaki, H; Khosravi, A; Gharanjig, K; Mahboubi, A
| HERO ID | 3418736 |
|---|---|
| In Press | No |
| Year | 2016 |
| Title | Investigation of synthesis, characterization, photophysical and biological properties of novel antimicrobial fluorescent naphthalimide derivatives |
| Authors | Shaki, H; Khosravi, A; Gharanjig, K; Mahboubi, A |
| Journal | Materials Technology |
| Volume | 31 |
| Issue | 6 |
| Page Numbers | 322-331 |
| Abstract | A series of 4-amino-N-substituted-1,8-naphthalimide and 4-allylamino-N-substituted-1,8-naphthalimide derivatives were synthesized from intermediate 4-nitro-1,8-naphthalimide by imidation, reduction and allylation reactions. These compounds were characterized by thin layer chromatography (TLC), differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FTIR), elemental analysis, H-1-nuclear magnetic resonance (1HNMR), C-13-NMR, liquid chromatography-mass spectroscopy, UV-Vis spectroscopy and fluorimetry. 1,8-Naphthalimide derivatives with amino and allylamino groups in the C-4 position exhibit fluorescent emission on irradiation. In addition, synthesized compounds had biological properties due to the presence of sulfonamide group (-SO2-N-) in their structure. The absorption maximum wavelength of synthesized dyes that are fluorescent is in the range of 427-439 nm while emitting in the range of 526-528.5 nm. The absorption spectra of synthesized dyes demonstrated that the type of substitutions in C-4 position and N-imide of naphthalimide ring had small effect on their colour. The photophysical characteristics of these dyes were assessed, and their Stokes shift values were determined in dimethylformamide solvent. The results demonstrated that Stokes shift values were between 3860 and 4469 cm(-1). Antibacterial and antifungal activities of the dyes were evaluated against gram positive and gram negative bacteria and Candida albicans fungi using cup plate, minimum inhibitory concentration and minimum bactericidal concentration methods. The results revealed that dye 10 had the most levels of antimicrobial activity against bacteria and fungi. |
| Doi | 10.1179/1753555715Y.0000000058 |
| Wosid | WOS:000375900800003 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | Naphthalimide dyes; Characterization; sulfonamides; Photophysical properties; Antimicrobial activity |