Related Experiment Video
Updated: Jan 20, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
Published on: August 12, 2019
A study of 99mTc/Re-tricarbonyl complexes of 4-amino-1,8-naphthalimides
William L Turnbull1, Emily Murrell1, Mariel Bulcan-Gnirss1
1Department of Chemistry, University of Western Ontario, London, Ontario N6A 3K7, Canada. lluyt@uwo.ca.
Abstract:
Three 4-amino-1,8-naphthalimide analogues were synthesized, consisting of the tridentate chelators di-2-picolylamine, (pyridin-2-ylmethyl)glycinate, and iminodiacetate conjugated to the naphthalimide scaffold. Coordination with fac-99mTc/Re(CO)3 resulted in metal complexes with overall charges of -1, 0, or +1. Upon coordination of Re(i), the initial naphthalimide-based fluorescence is largely maintained for both negative and neutral complexes compared to their free ligand forms, while an increase in fluorescence quantum yield was observed for the positively charged complex. OVCAR-8 ovarian cancer cells were stained with each of the complexes, demonstrating that the positive complex is more lipophilic and cell membrane permeable than the neutral and negative complexes. Each of the three technetium-99m labelled naphthalimide complexes were successfully produced from fac-[99mTc(CO)3(H2O)3]+ in 15 minutes at 70 °C and isolated in radiochemical yields ranging from 60-95% with radiochemical purities greater than 95%. These fluorescent metal complexes of various charges can be used to tune pharmacokinetic and cellular uptake properties of 99mTc/Re-naphthalimide-bioconjugates, while still maintaining desirable fluorescence properties.
Related Concept Videos
Amino acids
07:56Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
04:04Radiolabeled Amino Acid Uptake Assay to Quantify Cellular Uptake of Amino Acids
16:11Thermochemical Studies of Ni(II) and Zn(II) Ternary Complexes Using Ion Mobility-Mass Spectrometry
09:14Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Amino Acid Catabolism
