PGlu-3-methyl-His-Pro-NH2 TFA

• CAT Number: I046021
• Molecular Formula: C19H25F3N6O6
• Molecular Weight: 490.43
• Purity: ≥95%
• Synonyms: (2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(3-methylimidazol-4-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide;2,2,2-trifluoroacetic acid
• InChI: InChI=1S/C17H24N6O4.C2HF3O2/c1-22-9-19-8-10(22)7-12(21-16(26)11-4-5-14(24)20-11)17(27)23-6-2-3-13(23)15(18)25;3-2(4,5)1(6)7/h8-9,11-13H,2-7H2,1H3,(H2,18,25)(H,20,24)(H,21,26);(H,6,7)/t11-,12-,13-;/m0./s1
• InChIKey: XHROLUALQYBURQ-QKWXXBCPSA-N
• SMILES: CN1C=NC=C1CC(C(=O)N2CCCC2C(=O)N)NC(=O)C3CCC(=O)N3.C(=O)(C(F)(F)F)O

PGlu-3-methyl-His-Pro-NH2 TFA (A-42872 TFA), the modified thyrotropin-releasing hormone (TRH) peptide, enhances binding to pituitary TRH receptors and increases stimulation of thyroid-stimulating hormone (TSH) release from the pituitary. The in vitro permeability of PGlu-3-methyl-His-Pro-NH2 TFA through rat skin is increased in the presence of enhancers Ethanol and Cineole[1][2].
PGlu-3-methyl-His-Pro-NH2 TFA (A-42872 TFA) has a very high affinity for the TRH receptor in the CNS. PGlu-3-methyl-His-Pro-NH2 TFA is more potent in eliciting behavioral effects as well as being more potent in the release of both growth hormone and thyroid stimulating hormone[1].
PGlu-3-methyl-His-Pro-NH2 TFA (A-42872 TFA) (300 μg/kg; i.v.) elicits a 80 % increase in cerebral blood flow. Even a minute dose of PGlu-3-methyl-His-Pro-NH2 TFA (625 ng kg-1) causes an increase in cerebral blood flow[1].
The addition of 3% terpene in combination with 47% ethanol increases the penetration of PGlu-3-methyl-His-Pro-NH2 TFA (5 mg/ml; transdermal administration; 30 minutes)[2].
Topical application of PGlu-3-methyl-His-Pro-NH2 TFA induces an increase in TSH serum concentration from 0.32 ng/ml to 22.9 ng/ml, respectively, after 30 min. The addition of Terpene and Ethanol in combination with TRH or PGlu-3-methyl-His-Pro-NH2 TFA, increases the TSH release to 43 and 48.4 ng/ml, respectively[2].

Reference

[1]. Koskinen LO, et al. Cerebrovascular effects of the TRH analogues pGlu-3-methyl-His-Pro amide and pGlu-Glu-Pro amide: a comparison with TRH. Ups J Med Sci. 2000;105(1):73-83.
 [Content Brief]

[2]. Magnusson BM, et al. Biological effects after percutaneous absorption of thyrotropin-releasing hormone and its analogue M-TRH. Peptides. 2001 Jan;22(1):73-9.
 [Content Brief]