BIOMAT Database Logo BIOMAT Database Logo

Multi-fluorine labeled indanone derivatives as potential MRI imaging probes for β-Amyloid plaques. 2023

Yaqian Dai, and Tangni Fang, and Yuanhong Xu, and Taoshan Jiang, and Jinping Qiao
Department of Clinical Laboratory, The First Affiliated Hospital of Anhui Medical University, Hefei, China.

In order to realize the early diagnosis of Alzheimer's disease (AD), we designed and synthesized a series of multi-fluorine labeled indanone derivatives based on indanone which could target β-amyloid (Aβ). Through the in vitro staining experiment and affinity experiment, we selected 7d out, and then evaluated it through other in vivo and in vitro experiments. The staining of AD human brain adjacent sections revealed that compound 7d could bind to Aβ plaques with high affinity. In the in vitro binding assay, 7d showed a balanced affinity with Aβ1-40 (Kd = 367 ± 13) and Aβ1-42 (Kd = 384 ± 56). Also, 7d exhibited a low toxicity (LD50 > 50 mg/kg) and an excellent ability to pass through the blood-brain barrier (Log p = 3.87). The biodistribution experiment in mice showed that 7d reached the highest brain uptake after 1 h of tail vein injection and cleared after 24 h. A low concentration of 7d (1.875 mg/ml) showed a strong imaging ability (19F-weighted mode), and the imaging capability increased with the increasing of concentration. All the results showed that 7d could provide a feasible solution for the early diagnosis of AD under non-radioactive condition.

UI MeSH Term Description Entries
D007189 Indans Aryl CYCLOPENTANES that are a reduced (protonated) form of INDENES. Indanones
D008279 Magnetic Resonance Imaging Non-invasive method of demonstrating internal anatomy based on the principle that atomic nuclei in a strong magnetic field absorb pulses of radiofrequency energy and emit them as radiowaves which can be reconstructed into computerized images. The concept includes proton spin tomographic techniques. Chemical Shift Imaging,MR Tomography,MRI Scans,MRI, Functional,Magnetic Resonance Image,Magnetic Resonance Imaging, Functional,Magnetization Transfer Contrast Imaging,NMR Imaging,NMR Tomography,Tomography, NMR,Tomography, Proton Spin,fMRI,Functional Magnetic Resonance Imaging,Imaging, Chemical Shift,Proton Spin Tomography,Spin Echo Imaging,Steady-State Free Precession MRI,Tomography, MR,Zeugmatography,Chemical Shift Imagings,Echo Imaging, Spin,Echo Imagings, Spin,Functional MRI,Functional MRIs,Image, Magnetic Resonance,Imaging, Magnetic Resonance,Imaging, NMR,Imaging, Spin Echo,Imagings, Chemical Shift,Imagings, Spin Echo,MRI Scan,MRIs, Functional,Magnetic Resonance Images,Resonance Image, Magnetic,Scan, MRI,Scans, MRI,Shift Imaging, Chemical,Shift Imagings, Chemical,Spin Echo Imagings,Steady State Free Precession MRI
D008822 Mice, Transgenic Laboratory mice that have been produced from a genetically manipulated EGG or EMBRYO, MAMMALIAN. Transgenic Mice,Founder Mice, Transgenic,Mouse, Founder, Transgenic,Mouse, Transgenic,Mice, Transgenic Founder,Transgenic Founder Mice,Transgenic Mouse
D001921 Brain The part of CENTRAL NERVOUS SYSTEM that is contained within the skull (CRANIUM). Arising from the NEURAL TUBE, the embryonic brain is comprised of three major parts including PROSENCEPHALON (the forebrain); MESENCEPHALON (the midbrain); and RHOMBENCEPHALON (the hindbrain). The developed brain consists of CEREBRUM; CEREBELLUM; and other structures in the BRAIN STEM. Encephalon
D005461 Fluorine A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries. Fluorine-19,Fluorine 19
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000544 Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57) Acute Confusional Senile Dementia,Alzheimer's Diseases,Dementia, Alzheimer Type,Dementia, Senile,Presenile Alzheimer Dementia,Senile Dementia, Alzheimer Type,Alzheimer Dementia,Alzheimer Disease, Early Onset,Alzheimer Disease, Late Onset,Alzheimer Sclerosis,Alzheimer Syndrome,Alzheimer Type Senile Dementia,Alzheimer's Disease,Alzheimer's Disease, Focal Onset,Alzheimer-Type Dementia (ATD),Dementia, Presenile,Dementia, Primary Senile Degenerative,Early Onset Alzheimer Disease,Familial Alzheimer Disease (FAD),Focal Onset Alzheimer's Disease,Late Onset Alzheimer Disease,Primary Senile Degenerative Dementia,Senile Dementia, Acute Confusional,Alzheimer Dementias,Alzheimer Disease, Familial (FAD),Alzheimer Diseases,Alzheimer Type Dementia,Alzheimer Type Dementia (ATD),Alzheimers Diseases,Dementia, Alzheimer,Dementia, Alzheimer-Type (ATD),Familial Alzheimer Diseases (FAD),Presenile Dementia,Sclerosis, Alzheimer,Senile Dementia
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D014018 Tissue Distribution Accumulation of a drug or chemical substance in various organs (including those not relevant to its pharmacologic or therapeutic action). This distribution depends on the blood flow or perfusion rate of the organ, the ability of the drug to penetrate organ membranes, tissue specificity, protein binding. The distribution is usually expressed as tissue to plasma ratios. Distribution, Tissue,Distributions, Tissue,Tissue Distributions
D016229 Amyloid beta-Peptides Peptides generated from AMYLOID BETA-PEPTIDES PRECURSOR. An amyloid fibrillar form of these peptides is the major component of amyloid plaques found in individuals with Alzheimer's disease and in aged individuals with trisomy 21 (DOWN SYNDROME). The peptide is found predominantly in the nervous system, but there have been reports of its presence in non-neural tissue. Alzheimer beta-Protein,Amyloid Protein A4,Amyloid beta-Peptide,Amyloid beta-Protein,beta Amyloid,beta-Amyloid Protein,Alzheimer's ABP,Alzheimer's Amyloid Fibril Protein,Amyloid AD-AP,Amyloid Fibril Protein, Alzheimer's,Amyloid beta-Proteins,ABP, Alzheimer's,AD-AP, Amyloid,Alzheimer ABP,Alzheimer beta Protein,Alzheimers ABP,Amyloid AD AP,Amyloid beta Peptide,Amyloid beta Peptides,Amyloid beta Protein,Amyloid beta Proteins,Amyloid, beta,Protein A4, Amyloid,Protein, beta-Amyloid,beta Amyloid Protein,beta-Peptide, Amyloid,beta-Peptides, Amyloid,beta-Protein, Alzheimer,beta-Protein, Amyloid,beta-Proteins, Amyloid

Related Publications

Yaqian Dai, and Tangni Fang, and Yuanhong Xu, and Taoshan Jiang, and Jinping Qiao
Novel indanone derivatives as potential imaging probes for β-amyloid plaques in the brain.
July 2012, Chembiochem : a European journal of chemical biology,
Yaqian Dai, and Tangni Fang, and Yuanhong Xu, and Taoshan Jiang, and Jinping Qiao
6-Methoxy-indanone derivatives as potential probes for β-amyloid plaques in Alzheimer's disease.
November 2016, European journal of medicinal chemistry,
Yaqian Dai, and Tangni Fang, and Yuanhong Xu, and Taoshan Jiang, and Jinping Qiao
Novel ¹⁸F-labeled dibenzylideneacetone derivatives as potential positron emission tomography probes for in vivo imaging of β-amyloid plaques.
September 2014, European journal of medicinal chemistry,
Yaqian Dai, and Tangni Fang, and Yuanhong Xu, and Taoshan Jiang, and Jinping Qiao
¹⁸F-labeled 2-phenylquinoxaline derivatives as potential positron emission tomography probes for in vivo imaging of β-amyloid plaques.
November 2012, European journal of medicinal chemistry,
Yaqian Dai, and Tangni Fang, and Yuanhong Xu, and Taoshan Jiang, and Jinping Qiao
99mTc- and Re-labeled 6-dialkylamino-2-naphthylethylidene derivatives as imaging probes for β-amyloid plaques.
February 2011, Bioorganic & medicinal chemistry letters,
Yaqian Dai, and Tangni Fang, and Yuanhong Xu, and Taoshan Jiang, and Jinping Qiao
Diphenylpropynone derivatives as probes for imaging β-amyloid plaques in Alzheimer's brains.
January 2011, Bioorganic & medicinal chemistry letters,
Yaqian Dai, and Tangni Fang, and Yuanhong Xu, and Taoshan Jiang, and Jinping Qiao
Synthesis and biological evaluation of novel technetium-99m labeled phenylbenzoxazole derivatives as potential imaging probes for β-amyloid plaques in brain.
July 2012, Bioorganic & medicinal chemistry letters,
Yaqian Dai, and Tangni Fang, and Yuanhong Xu, and Taoshan Jiang, and Jinping Qiao
Novel ¹⁸F-labeled benzoxazole derivatives as potential positron emission tomography probes for imaging of cerebral β-amyloid plaques in Alzheimer's disease.
November 2012, Journal of medicinal chemistry,
Yaqian Dai, and Tangni Fang, and Yuanhong Xu, and Taoshan Jiang, and Jinping Qiao
Radiolabeled Chalcone Derivatives as Potential Radiotracers for β-Amyloid Plaques Imaging.
April 2023, Molecules (Basel, Switzerland),
Yaqian Dai, and Tangni Fang, and Yuanhong Xu, and Taoshan Jiang, and Jinping Qiao
(99m)Tc-labeled dibenzylideneacetone derivatives as potential SPECT probes for in vivo imaging of β-amyloid plaque.
June 2013, European journal of medicinal chemistry,
Copied contents to your clipboard!