Synthesis of a 4-nitroimidazole indocyanine dye-conjugate and imaging of tumor hypoxia in BALB/c tumor-bearing female mice

Bioreductive fluorescent imaging agents: applications to tumour hypoxia

“…Utilising the considerably more cost effective 4-nitroimidazole moiety Smith, Zhu and co-workers also recently reported the preparation of the 4-nitroimidazolepiperazine-indocyanine derivative 35. 47 The introduction of a 4-nitroimidazole moiety was shown to not significantly affect the retention of the dye in tumours where, in fact, 35 showed a 1.5-fold higher fluorescent intensity after 15 min post-injection compared to 33 when measured in BALB/c tumour-bearing female mice. However, there are some concerns around the toxicity of 4-nitroimidazole containing compounds 48 thus further research is on-going to determine any toxic effects associated with 35.…”

Functionalized Nitroimidazole Scaffold Construction and Their Pharmaceutical Applications: A 1950–2021 Comprehensive Overview

“…Abuteen et al developed 4-nitroimidazole bearing dye-conjugate ( 88a-b ) for the imaging of tumor hypoxia ( Scheme 28 ) [ 97 ]. The design is based on the nitroimidazoles property as molecular probes because they diffuse freely in the body and are irreversibly trapped by covalent binding to proteins in low oxygen environments.…”

“…Secnidazole displayed improved oral absorption and a longer terminal elimination half-life than antimicrobial agents in this class ( Figure 16 ). Secnidazole 12 is safe and well tolerated, and it is widely used for amoebiasis, giardiasis, trichomoniasis, and genitourinary infections [ 97 ]. The antiprotozoal and anti-amoebic activities of Secnidazole 12 are due to the reduction of the nitro group of nitroimidazole by ferredoxin [ 127 ].…”

Novel hybrid motifs of 4-nitroimidazole-piperazinyl tagged 1,2,3-triazoles: Synthesis, crystal structure, anticancer evaluations, and molecular docking study

“…Over the last fifteen years, our laboratory has been synthesizing several derivatives of new 5-substituted piperazinyl-4-nitroimidazole derivatives and their evaluation for anti -HIV activity [ 36 , 37 ]. The nitroimidazoles are a common class of compounds that have been extensively studied as molecular probes because they diffuse freely in the body and are irreversibly trapped by nucleophilic covalent binding to proteins in low oxygen environments [ 38 ]. 4-Nitroimidazoles derivatives have been studied as radiopharmaceuticals for probing tumor hypoxia and in therapeutic treatment, antifertility potential, and anti-tubercular profile [ 39 , 40 ].…”