 | |
| Names | |
|---|---|
| IUPAC name (2S,3R)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-hydroxybutanoic acid | |
| Other names L-tyrosyl-L-prolyl-L-tryptophyl-L-threonine | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| |
| |
| Properties | |
| C29H35N5O7 | |
| Molar mass | 565.618 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Hemorphin-4 is anendogenousopioid peptide of thehemorphin family which possessesantinociceptive properties and is derived from the β-chain ofhemoglobin in the bloodstream.[1][2] It contains atetrapeptide core with theamino acid sequence Tyr-Pro-Trp-Thr. Hemorphin-4 serves as a opioid receptor ligand that hasaffinities for theμ-,δ-, andκ-opioid receptors in the same range as the structurally relatedβ-casomorphins, although affinity to the κ-opioid receptor is markedly higher in comparison.[3] It acts as anagonist at these sites.[4] It presents high affinity for other receptors such as angiotensin IV, bombesin subtype 3 (hBRS-3), and thecorticotropin releasing factor (CRF).[5] Even though it exhibits lower binding affinity for opioid receptors relative to traditional opioid peptides such asendorphins andenkephalins; it may still influence opioid receptor systems due to its high tissue concentration.
Hemorphin-4 also hasinhibitory effects onangiotensin-converting enzyme (ACE),[6] and as a result, may play a role in the regulation ofblood pressure.[3] Notably, inhibition of ACE also reducesenkephalincatabolism.[7] Upon modifications withadamantane andcyclohexane, the Hemorphin-4 analog inhibitsinsulin-regulated aminopeptidase (IRAP) compared to other angiotensin IV inhibitors, making it a suitable candidate for pain, anxiety, and depression therapies.[5] In binding to the μ-opioid receptor, it has significant seizure-suppressing and pain-relieving properties and reduces involuntary bladder contractions in a similar manner to classic opioids.[8]
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