Cyclo(his-pro) TFA

Cyclo(his-pro) TFA (Cyclo(histidyl-proline) TFA) is an orally active cyclic dipeptide structurally related to tyreotropin-releasing hormone. Cyclo(his-pro) TFA could inhibit NF-κB nuclear accumulation. Cyclo(his-pro) TFA can cross the brain-blood-barrier and affect diverse inflammatory and stress responses.

Product information

CAS Number: 936749-56-3

Molecular Weight: 348.28

Formula: C13H15F3N4O4

Chemical Name: (3S,8aS)-3-[(1H-imidazol-5-yl)methyl]-octahydropyrrolo[1,2-a]pyrazine-1,4-dione; trifluoroacetic acid

Smiles: OC(=O)C(F)(F)F.O=C1[C@H](CC2=CN=CN2)NC(=O)[C@@H]2CCCN12

InChiKey: YOFCDSUBRJNLBB-OZZZDHQUSA-N

InChi: InChI=1S/C11H14N4O2.C2HF3O2/c16-10-9-2-1-3-15(9)11(17)8(14-10)4-7-5-12-6-13-7;3-2(4,5)1(6)7/h5-6,8-9H,1-4H2,(H,12,13)(H,14,16);(H,6,7)/t8-,9-;/m0./s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 260 mg/mL (746.53 mM; Need ultrasonic). H2O : 125 mg/mL (358.91 mM; ultrasonic and adjust pH to 10 with NaOH).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Cyclo(his-pro) TFA (Cyclo(histidyl-proline) TFA; 50 μM; 1-48 hours) increases the nuclear level of Nrf2 and inhibits NF-κB nuclear translocation. Cyclo(His-Pro) alone has no effect on nuclear translocation of these transcription factors. Cyclo(his-pro) TFA (50 μM; prior to PQ exposure for 48 hours) abolishes protein nitration that followed paraquat (PQ) exposure and lessenes its functional consequences, as shown by decrease in cell apoptosis, detected by caspase 3 activity and by cytochrome c release. Cyclo(his-pro) TFA inhibits NF-κB nuclear accumulation induced by paraquat in rat pheochromocytoma PC12 cells via the Nrf2/heme oxygenase-1 pathway.

In Vivo:

Cyclo(his-pro) TFA (Cyclo(histidyl-proline) TFA; 1.8 mg/ear; topical application on the right ear; 30 min prior to TPA) reduces TPA-induced ear oedema confirming that it can exert anti-inflammatory effect. Cyclo(his-pro) TFA exerts in vivo anti-inflammatory effects in the central nervous system by down-regulating hepatic and cerebral TNFα expression thereby counteracting LPS-induced gliosis. Moreover, by up-regulating Bip, Cyclo(his-pro) increases the ER stress sensitivity andtriggers the unfolded protein response to alleviate the ER stress.

Products are for research use only. Not for human use.