Leuoprorelin

Leuoprorelin is a peptide analog featuring aromatic, aliphatic, and charged residues arranged to promote helical and loop structures. Researchers use it to examine ligand-recognition geometry, backbone alignment, and solvent-driven folding. The sequence supports mapping of structural determinants within peptidomimetic frameworks.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Leuoprorelin(CAS 54785-87-4)

CAT No: R2305

CAS No:54785-87-4

Synonyms/Alias:Leuoprorelin;54785-87-4;L-LEU6-LEUPROLIDE;2LYN3CCQ3S;Leuprorelin EP Impurity C;CHEMBL4073387;AKOS024457320;FD109828;PD079376;(Des-Gly10,Leu6,Pro-NHEt 9)-LHRH trifluoroacetate salt;Pyr-His-Trp-Ser-Tyr-Leu-Leu-Arg-Pro-NHEt; pE-HWSYLLRP-NHEt;5-OXO-L-PROLYL-L-HISTIDYL-L-TRYPTOPHYL-L-SERYL-L-TYROSYL-L-LEUCYL-L-LEUCYL-L-ARGINYL-N-ETHYL-L-PROLINAMIDE;

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M.F/Formula
C59H84N16O12
M.W/Mr.
1209.4
Sequence
One Letter Code:XHWSYLLRP
Three Letter Code:H-Pyr-His-Trp-Ser-Tyr-Leu-Leu-Arg-Pro-NHEt

Leuprorelin is a synthetic nonapeptide analog of gonadotropin-releasing hormone (GnRH), designed to mimic the endogenous hormone's activity while offering enhanced stability and receptor affinity. As a potent GnRH agonist, leuprorelin plays a central role in modulating the hypothalamic-pituitary-gonadal axis, making it a valuable tool in the study of endocrine regulation, reproductive biology, and peptide-receptor interactions. Its ability to induce controlled hormonal responses has established it as a reference compound in both academic and industrial research settings, particularly where precise manipulation of gonadotropin secretion is required.

Endocrine Research: In the context of endocrine system investigations, leuprorelin is widely utilized to probe the regulation of luteinizing hormone (LH) and follicle-stimulating hormone (FSH) secretion. By binding to GnRH receptors in the anterior pituitary, it triggers an initial surge in gonadotropin release, followed by receptor desensitization and downregulation upon sustained exposure. This biphasic response enables researchers to dissect feedback mechanisms within the hypothalamic-pituitary-gonadal axis, assess the dynamics of hormone regulation, and model states of hormonal suppression or overstimulation in vitro and in vivo.

Peptide-Receptor Interaction Studies: Owing to its well-characterized structure and receptor specificity, leuprorelin serves as a model ligand in the exploration of peptide-receptor binding kinetics and signal transduction pathways. Researchers employ it to map GnRH receptor distribution, quantify binding affinities, and evaluate receptor-mediated cellular responses using radioligand binding assays, fluorescence labeling, or functional readouts such as calcium mobilization. These applications are critical for advancing the understanding of G protein-coupled receptor (GPCR) pharmacology and for benchmarking new GnRH analogs.

Reproductive Biology Models: The ability of leuprorelin to modulate gonadotropin and sex steroid production makes it an indispensable tool in reproductive biology research. It is routinely used to induce controlled suppression or stimulation of gonadal function in animal models, facilitating studies on gametogenesis, gonadal development, and hormonal feedback loops. Such models are instrumental in elucidating the molecular events underpinning fertility, puberty, and reproductive aging, as well as in the assessment of endocrine-disrupting compounds.

Peptide Synthesis and Analytical Standards: In peptide chemistry, leuprorelin is frequently employed as a reference standard for method development in analytical techniques such as high-performance liquid chromatography (HPLC) and mass spectrometry. Its defined sequence and physicochemical properties make it suitable for validating peptide purification protocols, calibrating detection systems, and benchmarking synthetic strategies. These uses support quality control and process optimization in both research and industrial peptide manufacturing environments.

Drug Discovery and Development Research: As a prototypical GnRH agonist, leuprorelin is incorporated into preclinical screening platforms to evaluate the efficacy and safety of novel peptide therapeutics targeting the GnRH receptor or related pathways. It provides a benchmark for comparing the pharmacodynamic profiles, receptor selectivity, and metabolic stability of new analogs. This role is crucial in the iterative process of structure-activity relationship (SAR) studies, facilitating rational design and optimization of next-generation peptide-based modulators.

InChI
InChI=1S/C59H84N16O12/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64)/t40-,41-,42-,43-,44-,45-,46-,47-,48-/m0/s1
InChI Key
GFIJNRVAKGFPGQ-UILVTTEASA-N

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