7,8-Dihydroxyflavone, also known as tropoflavin, is a naturally occurring flavone found in Godmania aesculifolia, Tridax procumbens, and primula tree leaves. It has been found to act as a potent and selective small-molecule agonist of the tropomyosin receptor kinase B (TrkB) (Kd ≈ 320 nM), the main signaling receptor of the neurotrophin brain-derived neurotrophic factor (BDNF). Tropoflavin is both orally bioavailable and able to penetrate the blood–brain barrier. A prodrug of tropoflavin with greatly improved potency and pharmacokinetics, R13 (and, formerly, R7), is under development for the treatment of Alzheimer’s disease.
7,8-Dihydroxyflavone powder Chemical Base Information
|Synonyms||7,8-DHF; 7,8-DIHYDROXYFLAVONE;7,8-dihydroxy-2-phenyl-4-benzopyrone; DIHYDROXYFLAVONE, 7,8-(RG); 7,8-Dihydroxyflavone hydrate; 7,8-dihydroxy-2-phenyl-1-benzopyran-4-one; 8-Dihydroxyflavone; 7,8-DIHYDROXYFLAVONE 7,8-DIHYDROXYFLAVONE; 7,8-dihydroxy-2-phenyl-4h-1-benzopyran-4-on|
|Boling Point||494.4° C at 760 mmHg|
|Solubility||DMSO : ≥ 100 mg/mL (393.33 mM) |
Soluble in DMSO, ethanol, and methanol.
|Storage Condition||room temp|
|Application||7,8-Dihydroxyflavone is a TrkB agonist that inhibits glutamate-triggered apoptosis|
7,8-Dihydroxyflavone powder General Description
7,8-Dihydroxyflavone (7,8-DHF) is a monophenolic flavone with diverse effects. It acts as an agonist of the neurotrophic tyrosine kinase receptor TrkB (Kd = 320 nM), protecting neurons that express TrkB from apoptosis.1 7,8-DHF is neuroprotective in an animal model of Parkinson’s disease.1 It supports emotional learning in mice and reverses memory deficits in a mouse model of Alzheimer’s disease.2,3 It also improves motor function and extends survival in an animal model of Huntington’s disease.4 7,8-DHF inhibits the cytochrome P450 aromatase (IC50 = 10 µM) and, in this way, alters estrogen metabolism.5 It also has antioxidant action that increases intracellular glutathione synthesis and scavenges reactive oxygen species.
7,8-Dihydroxyflavone powder History
In 2017, evidence was published suggesting that tropoflavin and various other reported small-molecule TrkB agonists might not actually be direct agonists of the TrkB and might be mediating their observed effects by other means.
7,8-Dihydroxyflavone powder Mechanism Of Action
7,8-Dihydroxyflavone is a selective tyrosine kinase receptor B (TrkB) receptor agonist. It manifests all the therapeutic effects of brain-derived neurotrophic factor (BDNF)—such as protecting neurons from apoptosis, inhibiting kainic acid-induced toxicity, decreasing infarct volumes in stroke, and neuroprotecting in an animal model of Parkinson′s disease—without the poor pharmacokinetic profile of BDNF limiting its therapeutic potential.
7,8-Dihydroxyflavone (7,8-DHF) may be used to help identify and differentiate the physiological effects and cell signaling pathways mediated by TrkB activation, such as those involving, memory, vasorelaxation and hypertension. 7,8-DHF elicits protection in scopolamine induced Alzheimer-like pathologic dysfunction.
7,8-Dihydroxyflavone powder Application
7,8-Dihydroxyflavone hydrate has been used as tropomyosin-receptor-kinase B (TrkB) agonist in mice and to inhibit TrkB for monitoring evoked excitatory postsynaptic currents (eEPSCs).
7,8-Dihydroxyflavone powder More research
A variety of close structural analogues of tropoflavin have also been found to act as TrkB agonists in vitro, including diosmetin (5,7,3′-trihydroxy-4′-methoxyflavone), norwogonin (5,7,8-trihydroxyflavone), eutropoflavin (4′-dimethylamino-7,8-dihydroxyflavone), 7,8,3′-trihydroxyflavone, 7,3′-dihydroxyflavone, 7,8,2′-trihydroxyflavone, 3,7,8,2′-tetrahydroxyflavone, and 3,7-dihydroxyflavone. The highly hydroxylated analogue gossypetin (3,5,7,8,3′,4′-hexahydroxyflavone), conversely, appears to be an antagonist of TrkB in vitro.
Tropoflavin was also found to decrease mouse sleep in dark phase and reduce hypothalamus level of orexin A but not orexin B in mice.
- Andero et al (2012) 7,8-dihydroxyflavone, a TrkB receptor agonist, blocks long-term spatial memory impairment caused by immobilzation stress in rats. Hippocampus 22 399
- Jang et al (2010) A selective TrkB agonist with potent neurotrophic activities by 7,8-dihydroxyflavone. Proc.Natl.Acad.Sci.USA 107 268
- Boltaev U, Meyer Y, Tolibzoda F, Jacques T, Gassaway M, Xu Q, Wagner F, Zhang YL, Palmer M, Holson E, Sames D (2017). “Multiplex quantitative assays indicate a need for reevaluating reported small-molecule TrkB agonists”. Sci Signal.
- Jiang Small-molecule TrkB receptor agonists improve motor function and extend survival in a mouse model of Huntington’s disease. Hum.Mol.Genet. 2013