Pramlintide, Acetate [Pro25, 28, 29]-Amylin(1-37), human, Amide

Product Name: Pramlintide, Acetate [Pro25, 28, 29]-Amylin(1-37), human, Amide

Sequence One Letter Code: KCNTATCATQRLANFLVHSSNNFGPILPPTNVGSNTY-NH2 (Disulfide bridge), acetate salt

Sequence Three Letter Code: H-Lys-Cys-Asn-Thr-Ala-Thr-Cys-Ala-Thr-Gln-Arg-Leu-Ala-Asn-Phe-Leu-Val-His-Ser-Ser-Asn-Asn-Phe-Gly-Pro-Ile-Leu-Pro-Pro-Thr-Asn-Val-Gly-Ser-Asn-Thr-Tyr-NH2 acetate salt (S-S Bond)

Cas No: 196078-30-5

Chemical Formula:C171H269N51O53S2

Molecular Weight: 3949.6

Purity: 95%

Form: Lyophilized

Storage Conditions: - 20 °C

Research Area: Diabetes and Metabolic Syndrome

SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N2CCC[C@H]2C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC3=CC=C(C=C3)O)C(=O)N)NC(=O)[C@@H]4CCCN4C(=O)CNC(=O)[C@H](CC5=CC=CC=C5)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC6=CNC=N6)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC7=CC=CC=C7)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C)NC(=O)[C@@H]8CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N8)[C@@H](C)O)C)[C@@H](C)O)CC(=O)N)NC(=O)[C@H](CCCCN)N.CC(=O)O

IUPAC: acetic acid;(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-4-amino-1-[[(2S)-1-[[2-[(2S)-2-[[(2S,3S)-1-[[(2S)-1-[(2S)-2-[(2S)-2-[[(2S,3R)-1-[[(2S)-4-amino-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]carbamoyl]pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-2-oxoethyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]-2-[[(2S,3R)-2-[[(2S)-2-[[(4R,7S,10S,13S,16S,19R)-16-(2-amino-2-oxoethyl)-19-[[(2S)-2,6-diaminohexanoyl]amino]-7,13-bis[(1R)-1-hydroxyethyl]-10-methyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]amino]propanoyl]amino]-3-hydroxybutanoyl]amino]pentanediamide

INCHIKEY: DTPWZYSUQQHRKD-VIUAGAKSSA-N

INCHI:

InChI=1S/C171H267N51O53S2.C2H4O2/c1-21-81(12)130(163(268)207-110(56-78(6)7)169(274)222-53-33-42-118(222)170(275)221-52-32-41-117(221)160(265)219-135(89(20)230)167(272)206-109(66-125(180)238)151(256)212-128(79(8)9)161(266)186-68-126(239)192-111(70-223)154(259)203-107(64-123(178)236)152(257)218-134(88(19)229)166(271)195-98(136(181)241)57-92-43-45-94(231)46-44-92)214-159(264)116-40-31-51-220(116)127(240)69-187-141(246)101(58-90-34-24-22-25-35-90)199-148(253)105(62-121(176)234)201-149(254)106(63-122(177)235)202-155(260)112(71-224)209-156(261)113(72-225)208-146(251)103(60-93-67-184-75-188-93)205-162(267)129(80(10)11)213-150(255)100(55-77(4)5)198-145(250)102(59-91-36-26-23-27-37-91)200-147(252)104(61-120(175)233)196-137(242)82(13)189-144(249)99(54-76(2)3)197-142(247)96(39-30-50-185-171(182)183)193-143(248)97(47-48-119(174)232)194-165(270)132(86(17)227)215-138(243)83(14)190-157(262)114-73-276-277-74-115(210-140(245)95(173)38-28-29-49-172)158(263)204-108(65-124(179)237)153(258)217-131(85(16)226)164(269)191-84(15)139(244)216-133(87(18)228)168(273)211-114;1-2(3)4/h22-27,34-37,43-46,67,75-89,95-118,128-135,223-231H,21,28-33,38-42,47-66,68-74,172-173H2,1-20H3,(H2,174,232)(H2,175,233)(H2,176,234)(H2,177,235)(H2,178,236)(H2,179,237)(H2,180,238)(H2,181,241)(H,184,188)(H,186,266)(H,187,246)(H,189,249)(H,190,262)(H,191,269)(H,192,239)(H,193,248)(H,194,270)(H,195,271)(H,196,242)(H,197,247)(H,198,250)(H,199,253)(H,200,252)(H,201,254)(H,202,260)(H,203,259)(H,204,263)(H,205,267)(H,206,272)(H,207,268)(H,208,251)(H,209,261)(H,210,245)(H,211,273)(H,212,256)(H,213,255)(H,214,264)(H,215,243)(H,216,244)(H,217,258)(H,218,257)(H,219,265)(H4,182,183,185);1H3,(H,3,4)/t81-,82-,83-,84-,85+,86+,87+,88+,89+,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,128-,129-,130-,131-,132-,133-,134-,135-;/m0./s1

Source / Species: human

Conjugation: Unconjugated

Code Nacres: NA.26

Application: Pramlintide Acetate [Pro25,28,29]-Amylin (1–37), human, Amide is a synthetic analogue of human amylin, consisting of 37 amino acids with proline substitutions at positions 25, 28, and 29 to enhance stability and reduce aggregation. It retains the native disulfide bond between Cys2 and Cys7 and features C-terminal amidation, preserving its bioactive conformation. As an amylinomimetic peptide, pramlintide replicates key physiological functions of endogenous amylin, including slowing gastric emptying, suppressing postprandial glucagon secretion, and promoting satiety. These effects contribute to improved glucose regulation and metabolic control. Pramlintide is widely used in metabolic and endocrine research to study glucose homeostasis, hormone signaling, and peptide-based therapeutic strategies for diabetes and related metabolic disorders.

Current Research: Pramlintide acetate, also known as [Pro25,28,29]-Amylin (1–37), human, amide, is a synthetic analogue of the endogenous peptide hormone amylin, co-secreted with insulin by pancreatic β-cells. Designed to overcome the instability and aggregation issues of native amylin, pramlintide incorporates proline substitutions at positions 25, 28, and 29, which significantly enhance peptide solubility and structural stability. It also retains the intramolecular disulfide bond between Cys2 and Cys7 and features C-terminal amidation, preserving the biologically active conformation necessary for receptor interaction. Because of these structural optimizations, pramlintide functions as a reliable amylinomimetic, replicating key physiological roles of endogenous amylin while offering improved pharmacological properties. This makes it an important tool in metabolic and endocrine research, particularly in studies focused on glucose regulation and peptide hormone signaling. Role of Amylin in Metabolic Homeostasis Amylin is a peptide hormone that complements insulin action in maintaining postprandial glucose control. While insulin primarily facilitates glucose uptake into tissues, amylin modulates the rate at which glucose enters the bloodstream and influences appetite-related pathways. Key physiological functions of amylin include: Slowing gastric emptying, reducing the rate of glucose absorption Suppressing postprandial glucagon secretion, limiting hepatic glucose output Promoting satiety, contributing to reduced food intake These combined effects help prevent rapid spikes in blood glucose levels following meals and support overall metabolic balance. Structural Optimization of Pramlintide Native human amylin has a strong tendency to aggregate and form amyloid fibrils, which limits its utility in both research and therapeutic applications. Pramlintide addresses this limitation through targeted amino acid substitutions. The introduction of proline residues at positions 25, 28, and 29 disrupts β-sheet formation, which is responsible for peptide aggregation. This modification enhances peptide stability without compromising its ability to bind to amylin receptors. Additionally, the preserved Cys2–Cys7 disulfide bond is critical for maintaining the correct three-dimensional structure required for receptor activation. The C-terminal amide group further supports receptor binding and biological activity. Together, these features make pramlintide a stable and bioactive analogue suitable for experimental and translational research. Mechanisms of Action Pramlintide exerts its effects through activation of amylin receptors, which are heterodimeric complexes composed of calcitonin receptors and receptor activity-modifying proteins (RAMPs). These receptors are expressed in multiple tissues, including the brain, gastrointestinal tract, and pancreas. Upon receptor activation, pramlintide influences several physiological pathways: Regulation of gastric motility, delaying nutrient delivery to the intestine Modulation of glucagon secretion, particularly during postprandial states Central nervous system signaling, contributing to satiety and appetite control Through these mechanisms, pramlintide helps coordinate glucose homeostasis and energy balance. Applications in Metabolic and Endocrine Research Pramlintide is widely used as a model peptide in studies investigating metabolic regulation, hormone signaling, and therapeutic strategies for diabetes. Its well-characterized biological activity makes it particularly valuable for examining the interplay between insulin, glucagon, and gut-derived signals. Common research applications include: Studies of glucose homeostasis and postprandial metabolism Investigation of hormone signaling pathways involving amylin receptors Evaluation of gastric emptying and nutrient absorption dynamics Appetite and satiety research in metabolic regulation models Development of peptide-based therapeutics for metabolic disorders Because it mimics endogenous amylin while offering improved stability, pramlintide is frequently used in both in vitro and in vivo experimental systems. Relevance to Diabetes and Metabolic Disorders Dysregulation of amylin signaling is associated with diabetes and metabolic disease, particularly in individuals with impaired β-cell function. In such conditions, the coordinated secretion of insulin and amylin is disrupted, leading to abnormalities in glucose control. Pramlintide provides a means to study how restoring amylin-like activity can improve metabolic outcomes. Its effects on glucagon suppression, gastric emptying, and satiety are particularly relevant for understanding therapeutic strategies aimed at controlling blood glucose and body weight. A Valuable Tool for Peptide-Based Therapeutic Research As a stable and biologically active analogue of human amylin, pramlintide acetate represents an important model for studying peptide hormone function and metabolic regulation. Its optimized structure enables reliable experimental use while maintaining key physiological activities of the native hormone. Through applications in glucose metabolism research, endocrine signaling studies, and drug development, pramlintide continues to support advances in understanding and targeting metabolic disorders, particularly those related to diabetes and energy balance regulation.