title: A novel fluorescent tag for labelling of some antisense oligonucleotides.
abstract: A new versatile fluorescent tag, 4-acetylamino-1,8-naphthalimido-N-caproic acid (NCA) has been synthesized and characterized, and the optimal conditions for the maximum fluorescence using this tag allow a sensitivity level of 10(-9) mol/l. Useful fluorescence is observed upon covalent linking of this tag via its activated carboxy end to an alkylamino moiety, activated by the use of carbonyldiimidazole and hexamethylenediamine at the 5'-termini of an octamer, d(TCTTGCTC), a 33-mer, and a 41-mer complementary to the tat initiator of the HIV-1 genome. A new method for the generation of alkylamino function at the 5'-termini of oligonucleotides by the use of N-(4-bromobutyl) phthalimide is also described. The variation in fluorescence with respect to alteration of chain length of the oligonucleotides has also been studied. The fluorescence exhibited by these oligodeoxynucleotide (ODN)-NCA conjugates suggests that they may have a potential application as experimental tools in medicine and molecular biology.
authors.affiliation: Department of Chemistry, University of Allahabad, India.
authors.forename: K K
authors.initials: KK
authors.lastname: Dubey
authors.forename: R K
authors.initials: RK
authors.lastname: Singh
authors.forename: K
authors.initials: K
authors.lastname: Misra
mesh_terms: D002208:Caproates / Q000032:analysis / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D005456:Fluorescent Dyes / Q000032:analysis / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D016376:Oligonucleotides, Antisense / Q000737:chemistry*; D011522:Protons; D012680:Sensitivity and Specificity; D013056:Spectrophotometry, Ultraviolet
chemical_list: C108027:4-acetylamino-1,8-naphthalimido-N-caproic acid; D002208:Caproates; D005456:Fluorescent Dyes; D016376:Oligonucleotides, Antisense; D011522:Protons