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Oxyntomodulin (human, mouse, rat)

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Oxyntomodulin (human, mouse, rat) can effectively inhibit gastric acid secretion and pancreatic enzyme secretion when infused iv. Furthermore, Oxyntomodulin injection into the intraventricular and hypothalamic paraventricular nucleus effectively and consistently inhibits food intake in both fasted and non-fasted animals.

Category

Peptide Inhibitors

Catalog number

BAT-015323

CAS number

159002-68-3

Molecular Formula

C192H295N61O60S

Molecular Weight

4449.83

Specification
Reference Reading

IUPAC Name

(3S)-4-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-4-amino-1-[[(2S,3S)-1-[[(1S)-1-carboxyethyl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S,3R)-2-[[2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]amino]-5-oxopentanoyl]amino]-4-oxobutanoic acid

Synonyms

OXM (human, mouse, rat); H-His-Ser-Gln-Gly-Thr-Phe-Thr-Ser-Asp-Tyr-Ser-Lys-Tyr-Leu-Asp-Ser-Arg-Arg-Ala-Gln-Asp-Phe-Val-Gln-Trp-Leu-Met-Asn-Thr-Lys-Arg-Asn-Arg-Asn-Asn-Ile-Ala-OH; Preproglucagon (53-89) (human, mouse, rat); Proglucagon (33-69) (human, mouse, rat); Glucagon-37 (human, mouse, rat); L-histidyl-L-seryl-L-glutaminyl-glycyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-alpha-aspartyl-L-tyrosyl-L-seryl-L-lysyl-L-tyrosyl-L-leucyl-L-alpha-aspartyl-L-seryl-L-arginyl-L-arginyl-L-alanyl-L-glutaminyl-L-alpha-aspartyl-L-phenylalanyl-L-valyl-L-glutaminyl-L-tryptophyl-L-leucyl-L-methionyl-L-asparagyl-L-threonyl-L-lysyl-L-arginyl-L-asparagyl-L-arginyl-L-asparagyl-L-asparagyl-L-isoleucyl-L-alanine

Appearance

White Powder

Purity

95%

Sequence

HSQGTFTSDYSKYLDSRRAQDFVQWLMNTKRNRNNIA

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C192H295N61O60S/c1-15-92(8)149(184(308)220-94(10)188(312)313)251-177(301)128(76-142(201)268)240-171(295)127(75-141(200)267)238-161(285)114(43-31-64-215-192(209)210)224-170(294)126(74-140(199)266)237-160(284)113(42-30-63-214-191(207)208)223-157(281)110(39-25-27-60-194)229-186(310)151(96(12)259)253-178(302)129(77-143(202)269)239-164(288)118(58-65-314-14)228-165(289)119(66-89(2)3)232-169(293)125(72-102-81-216-108-37-23-22-36-106(102)108)236-163(287)117(54-57-139(198)265)230-183(307)148(91(6)7)250-175(299)123(68-98-32-18-16-19-33-98)235-172(296)130(78-145(271)272)241-162(286)116(53-56-138(197)264)221-153(277)93(9)219-156(280)111(40-28-61-212-189(203)204)222-158(282)112(41-29-62-213-190(205)206)226-181(305)135(86-256)247-174(298)132(80-147(275)276)242-166(290)120(67-90(4)5)231-167(291)121(70-100-44-48-104(261)49-45-100)233-159(283)109(38-24-26-59-193)225-180(304)134(85-255)246-168(292)122(71-101-46-50-105(262)51-47-101)234-173(297)131(79-146(273)274)243-182(306)136(87-257)248-187(311)152(97(13)260)252-176(300)124(69-99-34-20-17-21-35-99)244-185(309)150(95(11)258)249-144(270)83-217-155(279)115(52-55-137(196)263)227-179(303)133(84-254)245-154(278)107(195)73-103-82-211-88-218-103/h16-23,32-37,44-51,81-82,88-97,107,109-136,148-152,216,254-262H,15,24-31,38-43,52-80,83-87,193-195H2,1-14H3,(H2,196,263)(H2,197,264)(H2,198,265)(H2,199,266)(H2,200,267)(H2,201,268)(H2,202,269)(H,211,218)(H,217,279)(H,219,280)(H,220,308)(H,221,277)(H,222,282)(H,223,281)(H,224,294)(H,225,304)(H,226,305)(H,227,303)(H,228,289)(H,229,310)(H,230,307)(H,231,291)(H,232,293)(H,233,283)(H,234,297)(H,235,296)(H,236,287)(H,237,284)(H,238,285)(H,239,288)(H,240,295)(H,241,286)(H,242,290)(H,243,306)(H,244,309)(H,245,278)(H,246,292)(H,247,298)(H,248,311)(H,249,270)(H,250,299)(H,251,301)(H,252,300)(H,253,302)(H,271,272)(H,273,274)(H,275,276)(H,312,313)(H4,203,204,212)(H4,205,206,213)(H4,207,208,214)(H4,209,210,215)/t92-,93-,94-,95+,96+,97+,107-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,148-,149-,150-,151-,152-/m0/s1

InChI Key

DDYAPMZTJAYBOF-ZMYDTDHYSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(C)C(=O)O)NC(=O)C(CC(=O)N)NC(=O)C(CC(=O)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(=O)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCCN)NC(=O)C(C(C)O)NC(=O)C(CC(=O)N)NC(=O)C(CCSC)NC(=O)C(CC(C)C)NC(=O)C(CC1=CNC2=CC=CC=C21)NC(=O)C(CCC(=O)N)NC(=O)C(C(C)C)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C(C)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CO)NC(=O)C(CC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CCCCN)NC(=O)C(CO)NC(=O)C(CC5=CC=C(C=C5)O)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C(CC6=CC=CC=C6)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(CCC(=O)N)NC(=O)C(CO)NC(=O)C(CC7=CNC=N7)N

1. Cellular and sub-cellular localisation of oxyntomodulin-like immunoreactivity in enteroendocrine cells of human, mouse, pig and rat

Mitchell T Ringuet, Efstathia Sioras, Therese E Fazio Coles, John B Furness, Patricia R Martins, Billie Hunne, Linda J Fothergill Cell Tissue Res . 2019 Feb;375(2):359-369. doi: 10.1007/s00441-018-2921-z.

We use a monoclonal antibody against the C-terminal of oxyntomodulin (OXM) to investigate enteroendocrine cells (EEC) in mouse, rat, human and pig. This antibody has cross-reactivity with the OXM precursor, glicentin (Gli) but does not recognise glucagon. The antibody stained EEC in the jejunum and colon of each species. We compared OXM/Gli immunoreactivity with that revealed by antibodies against structurally related peptides, GLP-1 and glucagon and against GIP and PYY that are predicted to be in some EEC that express OXM/Gli. We used super-resolution to locate immunoreactive vesicles. In the pancreas, OXM/Gli was in glucagon cells but was located in separate storage vesicles to glucagon. In jejunal EEC, OXM/Gli and GIP were in many of the same cells but often in separate vesicles, whereas PYY and OXM/Gli were commonly colocalised in the same storage vesicles of colonic EEC. When binding of anti-GLP-1 to the structurally related GIP was removed by absorption with GIP peptide, GLP-1 and OXM/Gli immunoreactivities were contained in the same population of EEC in the intestine. We conclude that anti-OXM/Gli is a more reliable marker than anti-GLP-1 for EEC expressing preproglucagon products. Storage vesicles that were immunoreactive for OXM/Gli were almost always immunoreactive for GLP-1. OXM concentrations, measured by ELISA, were highest in the distal ileum and colon. Lesser concentrations were found in more proximal parts of small intestine and pancreas. Very little was in the stomach. In EEC containing GIP and OXM/Gli, these hormones are packaged in different secretory vesicles. Separate packaging also occurred for OXM and glucagon, whereas OXM/Gli and PYY and OXM/Gli and GLP-1 were commonly contained together in secretory vesicles.

2. Partial agonism improves the anti-hyperglycaemic efficacy of an oxyntomodulin-derived GLP-1R/GCGR co-agonist

Bryn M Owen, Stephen R Bloom, Alejandra Tomas, Roxana-Maria Rujan, Maria Lucey, Fiona B Ashford, Ivan R Corrêa, Tricia M Tan, Phil Pickford, James Minnion, Christopher A Reynolds, Emma Rose McGlone, Ben Jones, Stavroula Bitsi, Giuseppe Deganutti, David J Hodson Mol Metab . 2021 Sep;51:101242. doi: 10.1016/j.molmet.2021.101242.

Objective:Glucagon-like peptide-1 and glucagon receptor (GLP-1R/GCGR) co-agonism can maximise weight loss and improve glycaemic control in type 2 diabetes and obesity. In this study, we investigated the cellular and metabolic effects of modulating the balance between G protein and β-arrestin-2 recruitment at GLP-1R and GCGR using oxyntomodulin (OXM)-derived co-agonists. This strategy has been previously shown to improve the duration of action of GLP-1R mono-agonists by reducing target desensitisation and downregulation.Methods:Dipeptidyl dipeptidase-4 (DPP-4)-resistant OXM analogues were generated and assessed for a variety of cellular readouts. Molecular dynamic simulations were used to gain insights into the molecular interactions involved. In vivo studies were performed in mice to identify the effects on glucose homeostasis and weight loss.Results:Ligand-specific reductions in β-arrestin-2 recruitment were associated with slower GLP-1R internalisation and prolonged glucose-lowering action in vivo. The putative benefits of GCGR agonism were retained, with equivalent weight loss compared to the GLP-1R mono-agonist liraglutide despite a lesser degree of food intake suppression. The compounds tested showed only a minor degree of biased agonism between G protein and β-arrestin-2 recruitment at both receptors and were best classified as partial agonists for the two pathways measured.Conclusions:Diminishing β-arrestin-2 recruitment may be an effective way to increase the therapeutic efficacy of GLP-1R/GCGR co-agonists. These benefits can be achieved by partial rather than biased agonism.

3. Gut peptides in the regulation of food intake and energy homeostasis

Stephen R Bloom, Kevin G Murphy, Waljit S Dhillo Endocr Rev . 2006 Dec;27(7):719-27. doi: 10.1210/er.2006-0028.

Gut hormones signal to the central nervous system to influence energy homeostasis. Evidence supports the existence of a system in the gut that senses the presence of food in the gastrointestinal tract and signals to the brain via neural and endocrine mechanisms to regulate short-term appetite and satiety. Recent evidence has shown that specific gut hormones administered at physiological or pathophysiological concentrations can influence appetite in rodents and humans. Gut hormones therefore have an important physiological role in postprandial satiety, and gut hormone signaling systems represent important pharmaceutical targets for potential antiobesity therapies. Our laboratory investigates the role of gut hormones in energy homeostasis and has a particular interest in this field of translational research. In this review we describe our initial studies and the results of more recent investigations into the effects of the gastric hormone ghrelin and the intestinal hormones peptide YY, pancreatic polypeptide, glucagon-like peptide-1, and oxyntomodulin on energy homeostasis. We also speculate on the role of gut hormones in the future treatment of obesity.