| Identification | Back Directory | [Name]
TTK21 | [CAS]
709676-56-2 | [Synonyms]
TTK21
TTK21(CBP-p300 activator TTK21)
Benzamide, N-[4-chloro-3-(trifluoromethyl)phenyl]-2-propoxy- | [Molecular Formula]
C17H15ClF3NO2 | [MDL Number]
MFCD34565070 | [MOL File]
709676-56-2.mol | [Molecular Weight]
357.75 |
| Chemical Properties | Back Directory | [Boiling point ]
369.8±42.0 °C(Predicted) | [density ]
1.321±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 3 mg/ml; DMSO: 5 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml; Ethanol: 2 mg/ml | [form ]
A crystalline solid | [pka]
12.22±0.70(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C17H15ClF3NO2/c1-2-9-24-15-6-4-3-5-12(15)16(23)22-11-7-8-14(18)13(10-11)17(19,20)21/h3-8,10H,2,9H2,1H3,(H,22,23) | [InChIKey]
AQJBXYBDNZHZRE-UHFFFAOYSA-N | [SMILES]
C(NC1=CC=C(Cl)C(C(F)(F)F)=C1)(=O)C1=CC=CC=C1OCCC |
| Hazard Information | Back Directory | [Description]
TTK21 is an activator of CBP/p300 histone acetyltransferase activity. It activates CBP/p300 histone acetyltransferase activity in a concentration-dependent manner with a maximal effect at a concentration of 275 μM, inducing acetylation of histones H3 and H4 in vitro but not H2B and H2A. TTK21, conjugated to glucose-based carbon nanospheres (CSP), crosses the blood-brain barrier and increases histone acetylation of H2B and H3 as well as H4K12 in mouse frontal cortex and H2B and H3 in the dorsal hippocampus and brainstem. CSP-TTK21 (20 mg/kg) also induces differentiation and maturation of neuronal progenitors in adult mice's subgranular zone of the dentate gyrus. It increases memory duration in the Morris water maze, with mice spending more time in the platform quadrant than untreated mice up to 16 days after learning.
| [Uses]
N-[4-Chloro-3-(trifluoromethyl)phenyl]-2-propoxybenzamide was used in preparation of benzamide compounds as modulators of enzymes histone acetyltransferases and chromatin transcription. | [in vivo]
CSP-TTK21 (20 mg/kg; i.p.; single dose) can extend the memory duration[1].
CSP-TTK21 (20 mg/kg; p.o; single dose) enhances long-term potentiation comparably to intraperitoneal injection, suggesting effective memory enhancement in Wild-type mice[3].
CSP-TTK21 (10 mg/kg; p.o; weekly) promotes motor recovery after spinal cord injury in rats, and enhances the expression of regeneration-associated genes in the prefrontal cortex and cerebellum following spinal cord injury[3].
| Animal Model: | B57BL/6J male [1] | | Dosage: | CSP-TTK21; 20 mg/kg; single dose | | Administration: | i.p. | | Result: | Increased histone acetylation significantly in the hippocampus and frontal cortex. CSP-TTK21 crossed the blood-brain barrier and was primarily detected in the brain, liver, and spleen. It promoted differentiation of newly generated neurons in the dentate gyrus.
Mice with CSP-TTK21 displayed a persistent memory of the platform location in a Morris water maze task for a longer period compared to controls, demonstrating enhanced long-term memory. |
| Animal Model: | Wild-type mice [3] | | Dosage: | CSP-TTK21; 20 mg/kg; single dose | | Administration: | p.o. | | Result: | The administered compound crossed the blood-brain barrier, induced histone acetylation specifically H4K12ac and H3K14ac marks in the hippocampus, and did not alter basal synaptic transmission. It was found to enhance long-term potentiation comparably to intraperitoneal injection, suggesting effective memory enhancement through oral delivery.
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| Animal Model: | rats with spinal cord injury[3] | | Dosage: | CSP-TTK21; 10 mg/kg; weekly | | Administration: | p.o. | | Result: | Rats with CSP-TTK21 showed significant improvement in locomotion and rearing activity compared to controls. Histone acetylation was notably increased in the spinal cord, suggesting enhanced gene expression linked to regeneration and functional recovery.
Enhanced histone acetylation levels (H4K12ac, H3K27ac, H3K9ac) were observed in the prefrontal cortex and cerebellum of rats with CSP-TTK21, indicating active epigenetic modifications that support neuronal regeneration and functional recovery.
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| [IC 50]
CBP/p300 | [storage]
Store at -20°C | [References]
[1] SNEHAJYOTI CHATTERJEE. A novel activator of CBP/p300 acetyltransferases promotes neurogenesis and extends memory duration in adult mice.[J]. Journal of Neuroscience, 2013: 10698-10712. DOI: 10.1523/jneurosci.5772-12.2013 |
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