Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde.
Eight novel heterocyclic Schiff bases derived from the condensation reactions of indole 3-carboxaldehyde with different l-amino acids (histidine, glutamic acid, aspartic acid, leucine, valine) as well as with some aminophenols, have been synthesized and characterized by various spectroscopic methods (IR, MS, (1)H NMR). Schiff base derivatives of indole 3-carboxaldehyde were labeled with (99m)Tc and radiochemical purity was above 97% which is ascertained by instant thin layer chromatography using different solvent conditions. Stability studies of all the derivatives of indole 3-carboxaldehyde was determined under physiological conditions and were stable for more than 24h. Blood clearance showed a quick wash out from the circulation and biological half life was found to be t((1/2))(F)=1h 15min; t((1/2))(S)=10h 05min. Excellent quality radioimages of tumor bearing mice were recorded showing rapid clearance of background activity, visualization of tumor at 3h and clearance from kidneys of histidine analogue which was further evidenced in biodistribution studies. Antimicrobial activity of these Schiff base compounds was evaluated against Bacillus subtilis, Pseudomonas fluorescence, Staphylococcus aureus, Aspergillus niger, Candida albicans and Trichophyton rubrum.
Sinha
Deepa
D
Division of Cyclotron and Radiopharmaceutical Sciences, Institute of Nuclear Medicine and Allied Sciences, Brig. S. K. Mazumdar Road, Delhi 110054, India.
Tiwari
Anjani K
AK
Singh
Sweta
S
Shukla
Gauri
G
Mishra
Pushpa
P
Chandra
Harish
H
Mishra
Anil K
AK
D000818:Animals; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D018698:Glutamic Acid / Q000031:analogs & derivatives / Q000493:pharmacokinetics; D006207:Half-Life; D006639:Histidine / Q000031:analogs & derivatives / Q000493:pharmacokinetics; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D051379:Mice; D009369:Neoplasms / Q000378:metabolism; D011817:Rabbits; D012545:Schiff Bases / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology*; D013667:Technetium; D014018:Tissue Distribution
D007211:Indoles; D012545:Schiff Bases; D018698:Glutamic Acid; D006639:Histidine; D013667:Technetium; C012381:indole-3-carbaldehyde