[Phe2,Nle4] ACTH (1-24), human

Product Name:[Phe2,Nle4] ACTH (1-24), human

Form:TFA salt

Purity:95%

Storage:2-8 degree Celsius

Cas No:97773-00-7

Molar Mass:2899.4

Chemical Formula:C137H212N40O30

IUPAC Name:(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-1-[(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-4-carboxybutanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]acetyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]acetyl]amino]hexanoyl]amino]hexanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]hexanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carboxylic acid

SMILES:CCCC[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC1=CNC=N1)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N5CCC[C@H]5C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N6CCC[C@H]6C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC7=CC=C(C=C7)O)C(=O)N8CCC[C@H]8C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC9=CC=CC=C9)NC(=O)[C@H](CO)N

InChIKey:OIPMQAUTERWDFC-IXBZEBJWSA-N

InChI:InChI=1S/C137H212N40O30/c1-8-9-37-90(162-125(197)103(75-179)171-123(195)98(166-113(185)87(142)74-178)65-80-32-12-10-13-33-80)116(188)163-95(53-54-109(183)184)120(192)169-101(69-84-71-149-76-156-84)124(196)167-99(66-81-34-14-11-15-35-81)122(194)161-94(44-27-60-151-136(145)146)119(191)168-100(68-83-70-153-88-38-17-16-36-86(83)88)114(186)154-72-108(182)158-96(42-21-25-58-141)131(203)175-62-29-46-104(175)126(198)173-110(77(2)3)128(200)155-73-107(181)157-89(39-18-22-55-138)115(187)159-91(40-19-23-56-139)117(189)160-93(43-26-59-150-135(143)144)118(190)165-97(45-28-61-152-137(147)148)132(204)176-63-30-47-105(176)127(199)174-112(79(6)7)129(201)164-92(41-20-24-57-140)121(193)172-111(78(4)5)130(202)170-102(67-82-49-51-85(180)52-50-82)133(205)177-64-31-48-106(177)134(206)207/h10-17,32-36,38,49-52,70-71,76-79,87,89-106,110-112,153,178-180H,8-9,18-31,37,39-48,53-69,72-75,138-142H2,1-7H3,(H,149,156)(H,154,186)(H,155,200)(H,157,181)(H,158,182)(H,159,187)(H,160,189)(H,161,194)(H,162,197)(H,163,188)(H,164,201)(H,165,190)(H,166,185)(H,167,196)(H,168,191)(H,169,192)(H,170,202)(H,171,195)(H,172,193)(H,173,198)(H,174,199)(H,183,184)(H,206,207)(H4,143,144,150)(H4,145,146,151)(H4,147,148,152)/t87-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,110-,111-,112-/m0/s1

Sequence:Ser-Phe-Ser-Nle-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-Gly-Lys-Lys-Arg-Arg-Pro-Val-Lys-Val-Tyr-Pro

Application:

[Phe²,Nle⁴] ACTH (1-24), human is an analog of the adrenocorticotropic hormone (ACTH) fragment (1-24) with modified amino acid residues, phenylalanine at position 2 and norleucine at position 4. This synthetic peptide is designed to enhance ACTH receptor binding and stability while retaining its biological activity in stimulating adrenal corticosteroid production. It is widely utilized in endocrinology and neurobiology research, particularly for investigating adrenal function, melanocortin receptor interactions, and stress-related disorders. This modified ACTH fragment serves as a tool in evaluating the physiological and pharmacological roles of melanocortins in inflammation, metabolic regulation, and neurological disorders.

Current Research:

Introduction
Adrenocorticotropic hormone (ACTH) is a key regulator of adrenal steroidogenesis, acting through the melanocortin 2 receptor (MC2R) to stimulate cortisol and other glucocorticoid production. ACTH (1-24) represents the biologically active segment of endogenous ACTH, with synthetic modifications such as [Phe²,Nle⁴] designed to improve receptor binding and metabolic stability. Recent studies have explored its role in endocrinology, metabolic disorders, immune regulation, and neurobiology.

Endocrine and Metabolic Research
Modified ACTH analogs, including [Phe²,Nle⁴] ACTH (1-24), have been widely studied for their potential to enhance adrenal steroidogenesis. Research indicates that these modifications can increase receptor affinity and prolong biological half-life, making them valuable for investigating adrenal insufficiency and related disorders. Additionally, ACTH and its derivatives are being explored as therapeutic candidates for conditions such as Addison’s disease and congenital adrenal hyperplasia.

Furthermore, ACTH peptides are involved in metabolic regulation beyond their adrenal functions. Studies suggest that melanocortin system activation influences glucose homeostasis, insulin sensitivity, and lipid metabolism. These findings have raised interest in ACTH analogs as potential modulators of metabolic diseases, including obesity and diabetes.

Neurobiological and Behavioral Studies
The melanocortin system, particularly ACTH and its analogs, plays a significant role in neuroendocrine signaling related to stress response, cognition, and behavior. Research suggests that [Phe²,Nle⁴] ACTH (1-24) may influence neurotransmitter release, neuroprotection, and synaptic plasticity. Studies in animal models indicate that ACTH-derived peptides exhibit potential antidepressant and anxiolytic properties, supporting their role in stress and mood disorder research.

Additionally, ACTH fragments interact with melanocortin receptors in the central nervous system, contributing to neuroinflammatory regulation. This has implications for neurodegenerative diseases, such as Alzheimer’s and Parkinson’s, where inflammation and oxidative stress are critical factors. Researchers continue to explore the potential of ACTH-based peptides in neuroprotective strategies.

Immunological Implications
ACTH analogs, including [Phe²,Nle⁴] ACTH (1-24), exhibit immunomodulatory properties by influencing cytokine release and immune cell function. Their role in regulating inflammatory responses has been investigated in autoimmune diseases and inflammatory disorders, including multiple sclerosis and rheumatoid arthritis. The interaction of ACTH peptides with the melanocortin system suggests potential therapeutic applications for immune-related conditions.

Conclusion
Current research on [Phe²,Nle⁴] ACTH (1-24), human, highlights its importance in endocrinology, neurobiology, metabolic disease, and immunology. Its modified structure enhances stability and receptor interactions, making it a valuable tool in studying adrenal function, metabolic regulation, and neuroinflammation. Ongoing investigations continue to uncover its potential in therapeutic applications for endocrine disorders, neurological diseases, and immune-mediated conditions.