Acyline

Acyline is a potent gonadotropin-releasing hormone (GnRH) antagonist primarily used in biomedical research. It is employed to study the role of GnRH signaling in reproductive health, particularly for its possible therapeutic applications in treating hormone-dependent cancers, such as breast and prostate cancers. Acyline's mechanism of action involves blocking the release of GnRH, leading to reduced hormone secretion.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Acyline(CAS 170157-13-8)

CAT No: R1995

CAS No:170157-13-8

Synonyms/Alias:Acyline;MER-104;170157-13-8;UNII-S3439D3B35;S3439D3B35;CHEMBL262747;D-Alaninamide, N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-4-(acetylamino)-L-phenylalanyl-4-(acetylamino)-D-phenylalanyl-L-leucyl-N6-(1-methylethyl)-L-lysyl-L-prolyl-;DTXCID5091303;BDBM50102456;DB11906;DA-50214;HY-16027;CS-0006118;Q27288520;Ac-D-Nal-[D-(pCl)Phe]-D-Pal-Ser-[Aph(Ac)]-D-[Aph(Ac)]-Leu-ILys-Pro-DAla-NH2;

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M.F/Formula
C80H102ClN15O14
M.W/Mr.
1533.2
Sequence
One Letter Code:XXXSXXLXPA
Three Letter Code:Ac-D-2Nal-D-Phe(4-Cl)-D-3Pal-Ser-Phe(4-NHAc)-D-Phe(4-NHAc)-Leu-Lys(iPr)-Pro-D-Ala-NH2

Acyline is a synthetic peptide that functions as a potent gonadotropin-releasing hormone (GnRH) antagonist, recognized for its ability to modulate reproductive hormone signaling pathways. Structurally designed to competitively inhibit the binding of endogenous GnRH to its pituitary receptor, it effectively suppresses downstream secretion of luteinizing hormone (LH) and follicle-stimulating hormone (FSH). Its high receptor affinity and metabolic stability have made it a valuable tool in the investigation of neuroendocrine regulation, reproductive biology, and peptide-based drug mechanisms. Researchers utilize Acyline to dissect the physiological and molecular roles of GnRH signaling, as well as to develop advanced models for endocrine studies.

Endocrine research: In the context of neuroendocrinology, Acyline is widely employed to probe the regulatory mechanisms governing the hypothalamic-pituitary-gonadal (HPG) axis. By selectively antagonizing GnRH receptors, it allows investigators to achieve rapid and reversible suppression of gonadotropin release, facilitating precise analysis of hormonal feedback loops and the temporal dynamics of reproductive hormone regulation. This approach is instrumental in clarifying the physiological contributions of GnRH in both basal and stimulated states.

Peptide antagonist characterization: As a model GnRH antagonist, Acyline serves as a reference compound for evaluating the pharmacodynamic and pharmacokinetic profiles of novel peptide-based inhibitors. Its well-characterized activity enables comparative studies aimed at optimizing antagonist potency, duration of action, and receptor selectivity. Such investigations are critical for advancing the rational design of next-generation peptide therapeutics targeting hormone-dependent pathways.

Reproductive biology studies: The compound's ability to modulate pituitary gonadotropin secretion makes it a key reagent in experimental systems exploring the control of fertility, gonadal development, and sexual maturation. Researchers leverage its specific mechanism to create controlled states of hypogonadism or gonadotropin suppression in animal models, thereby enabling the study of reproductive physiology, gametogenesis, and the impact of hormonal manipulation on developmental processes.

Peptide synthesis and analytical validation: Due to its complex structure and sequence modifications, Acyline is utilized as a benchmark in peptide synthesis research and analytical method development. Synthesis laboratories and analytical chemists use it to validate solid-phase peptide synthesis protocols, assess peptide purity, and refine mass spectrometry or chromatographic techniques for peptide characterization. Its inclusion in such workflows supports quality assurance and methodological innovation in peptide chemistry.

Mechanistic studies of GnRH signaling: The use of this GnRH antagonist extends to mechanistic research aimed at delineating receptor-ligand interactions and downstream signaling cascades. By providing a tool to selectively block GnRH receptor activation, it enables detailed exploration of receptor conformational dynamics, intracellular signaling events, and the molecular determinants of antagonist efficacy. Insights gained from these studies inform the broader understanding of G protein-coupled receptor (GPCR) biology and the development of targeted peptide modulators.

InChI
InChI=1S/C80H102ClN15O14/c1-46(2)37-63(72(102)89-62(18-11-12-35-84-47(3)4)80(110)96-36-14-19-70(96)79(109)85-48(5)71(82)101)90-74(104)66(40-53-23-30-60(31-24-53)86-49(6)98)92-76(106)67(41-54-25-32-61(33-26-54)87-50(7)99)94-78(108)69(45-97)95-77(107)68(43-56-15-13-34-83-44-56)93-75(105)65(39-52-21-28-59(81)29-22-52)91-73(103)64(88-51(8)100)42-55-20-27-57-16-9-10-17-58(57)38-55/h9-10,13,15-17,20-34,38,44,46-48,62-70,84,97H,11-12,14,18-19,35-37,39-43,45H2,1-8H3,(H2,82,101)(H,85,109)(H,86,98)(H,87,99)(H,88,100)(H,89,102)(H,90,104)(H,91,103)(H,92,106)(H,93,105)(H,94,108)(H,95,107)/t48-,62+,63+,64-,65-,66-,67+,68-,69+,70+/m1/s1
InChI Key
ZWNUQDJANZGVFO-YHSALVGYSA-N

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