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Glucagon-like peptide 1 (1-37), human

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

Glucagon-like peptide 1 (1-37) is a pancreatic hormone synthesized by post-translational processing of proglucagon. It decreases plasma glucose level in high-fat-fed mice when administered at 25 nmol/kg. Glucagon-like peptide 1 (1-37) exhibits no effect on food intake in rats and does not enhance pancreatic insulin secretion. However it induces insulin expression in intestinal epithelial cells, which can restore glucose homeostasis when implanted into diabetic mice.

Category

Peptide Inhibitors

Catalog number

BAT-010492

CAS number

87805-34-3

Molecular Formula

C186H275N51O59

Molecular Weight

4169.48

Size	Price	Stock	Quantity
5 mg	$598	In stock

Specification
Reference Reading

IUPAC Name

(4S)-5-[[2-[[(2S,3R)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[2-[[(2S)-5-carbamimidamido-1-(carboxymethylamino)-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxohexan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-2-oxoethyl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-5-yl)propanoyl]amino]-3-carboxypropanoyl]amino]-4-carboxybutanoyl]amino]-3-phenylpropanoyl]amino]-4-carboxybutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]propanoyl]amino]-5-oxopentanoic acid

Synonyms

HuGLP-1; GLP-1 (1-37) (human, bovine, guinea pig, mouse, rat); Preproglucagon (92-128) (human, bovine, guinea pig, mouse, rat); H-His-Asp-Glu-Phe-Glu-Arg-His-Ala-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Lys-Glu-Phe-Ile-Ala-Trp-Leu-Val-Lys-Gly-Arg-Gly-OH; L-histidyl-L-alpha-aspartyl-L-alpha-glutamyl-L-phenylalanyl-L-alpha-glutamyl-L-arginyl-L-histidyl-L-alanyl-L-alpha-glutamyl-glycyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-alpha-aspartyl-L-valyl-L-seryl-L-seryl-L-tyrosyl-L-leucyl-L-alpha-glutamyl-glycyl-L-glutaminyl-L-alanyl-L-alanyl-L-lysyl-L-alpha-glutamyl-L-phenylalanyl-L-isoleucyl-L-alanyl-L-tryptophyl-L-leucyl-L-valyl-L-lysyl-glycyl-L-arginyl-glycine

Appearance

White or Off-white Lyophilized Powder

Purity

≥95%

Sequence

HDEFERHAEGTFTSDVSSYLEGQAAKEFIAWLVKGRG

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C186H275N51O59/c1-17-94(10)149(182(294)209-98(14)155(267)220-128(73-105-78-199-111-42-28-27-41-109(105)111)171(283)223-123(68-91(4)5)173(285)234-147(92(6)7)180(292)219-113(43-29-31-63-187)158(270)200-81-136(245)210-112(45-33-65-197-185(191)192)157(269)203-84-146(262)263)236-174(286)126(70-102-37-23-19-24-38-102)225-165(277)120(55-61-142(254)255)216-162(274)114(44-30-32-64-188)212-153(265)96(12)206-152(264)95(11)207-161(273)118(51-57-135(190)244)211-137(246)82-201-160(272)117(53-59-140(250)251)215-168(280)122(67-90(2)3)222-170(282)125(72-104-47-49-108(243)50-48-104)226-177(289)132(85-238)230-179(291)134(87-240)231-181(293)148(93(8)9)235-176(288)131(77-145(260)261)228-178(290)133(86-239)232-184(296)151(100(16)242)237-175(287)127(71-103-39-25-20-26-40-103)229-183(295)150(99(15)241)233-138(247)83-202-159(271)116(52-58-139(248)249)213-154(266)97(13)208-167(279)129(75-107-80-196-89-205-107)227-163(275)115(46-34-66-198-186(193)194)214-164(276)119(54-60-141(252)253)217-169(281)124(69-101-35-21-18-22-36-101)224-166(278)121(56-62-143(256)257)218-172(284)130(76-144(258)259)221-156(268)110(189)74-106-79-195-88-204-106/h18-28,35-42,47-50,78-80,88-100,110,112-134,147-151,199,238-243H,17,29-34,43-46,51-77,81-87,187-189H2,1-16H3,(H2,190,244)(H,195,204)(H,196,205)(H,200,270)(H,201,272)(H,202,271)(H,203,269)(H,206,264)(H,207,273)(H,208,279)(H,209,294)(H,210,245)(H,211,246)(H,212,265)(H,213,266)(H,214,276)(H,215,280)(H,216,274)(H,217,281)(H,218,284)(H,219,292)(H,220,267)(H,221,268)(H,222,282)(H,223,283)(H,224,278)(H,225,277)(H,226,289)(H,227,275)(H,228,290)(H,229,295)(H,230,291)(H,231,293)(H,232,296)(H,233,247)(H,234,285)(H,235,288)(H,236,286)(H,237,287)(H,248,249)(H,250,251)(H,252,253)(H,254,255)(H,256,257)(H,258,259)(H,260,261)(H,262,263)(H4,191,192,197)(H4,193,194,198)/t94-,95-,96-,97-,98-,99+,100+,110-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,147-,148-,149-,150-,151-/m0/s1

InChI Key

UKVFVQPAANCXIL-FJVFSOETSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(C)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(CCCCN)C(=O)NCC(=O)NC(CCCNC(=N)N)C(=O)NCC(=O)O)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CCC(=O)O)NC(=O)C(CCCCN)NC(=O)C(C)NC(=O)C(C)NC(=O)C(CCC(=O)N)NC(=O)CNC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(C(C)C)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C(CC5=CC=CC=C5)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(CCC(=O)O)NC(=O)C(C)NC(=O)C(CC6=CN=CN6)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(=O)O)NC(=O)C(CC7=CC=CC=C7)NC(=O)C(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CC8=CN=CN8)N

1. Glucagon-like peptide-1(1-37) inhibits chemokine-induced migration of human CD4-positive lymphocytes

Philipp Heinz, Mirjam Ostertag, Nikolaus Marx, Mathias Burgmaier, Angelina Hausauer, Helga Bach, Vinzenz Hombach, Renate Durst, Daniel Walcher Cell Mol Life Sci . 2010 Oct;67(20):3549-55. doi: 10.1007/s00018-010-0396-5.

The present study examined the effect of GLP-1(1-37) on chemokine-induced CD4-positive lymphocyte migration as an early and critical step in atherogenesis. Pretreatment with GLP-1(1-37) reduced the SDF-induced migration of isolated human CD4-positive lymphocytes in a concentration-dependent manner. Similar effects were seen when RANTES was used as a chemokine. GLP-1(1-37)'s effect on CD4-positive lymphocyte migration was mediated through an early inhibition of chemokine-induced PI-3 kinase activity. Downstream, GLP-1(1-37) inhibited SDF-induced phosphorylation of MLC and cofilin and limited f-actin formation as well as ICAM3 translocation. Furthermore, exendin-4 inhibited SDF-induced migration of CD4-positive lymphocytes similarly to GLP-1(1-37), and transfection of these cells with GLP-1 receptor siRNA abolished GLP-1(1-37)'s action on chemokine-induced ICAM3 translocation, suggesting an effect mediated via the GLP-1 receptor. Thus, GLP-1(1-37) inhibits chemokine-induced CD4-positive lymphocyte migration by inhibition of the PI3-kinase pathway and via the GLP-1 receptor. This effect provides a potential novel mechanism for how GLP-1(1-37) may modulate vascular disease.

2. Glucagon-like peptide-1(1-37) can enhance blood glucose homeostasis in mice

Xun Lao, Haifeng Ye, Zirong Wu, Dongqing Li, Juan Li, Jing Huang, Lei Xiao, Zhenghua Wang, Lifen Zhao Regul Pept . 2012 Oct 10;178(1-3):1-5. doi: 10.1016/j.regpep.2012.06.010.

Glucagon-like peptide-1 (GLP-1) is produced by the posttranslational processing of proglucagon and acts as a regulator of various homeostatic events. No blood glucose regulation role of GLP-1(1-37) has previously been identified. However, our findings in this study clearly showed that GLP-1(1-37) could lower blood glucose levels both in normal and diabetic mice. In vitro stability analysis demonstrated that GLP-1(1-37) was more stable than GLP-1(7-37), with 94.7% of the initial amount of peptide left after a 4h exposure to mouse serum. Moreover, GLP-1(1-37) was confirmed to be a highly potent agonist of the GLP-1 receptor (GLP-1R) by measuring the expression of the luciferase reporter gene expression in transiently transfected human embryonic kidney (HEK293) cells. Unlike the glucose lowering effect of GLP-1(7-37), the glucose-lowering effect of GLP-1(1-37) could not be blocked by the GLP-1R antagonist exendin(9-39), suggesting that GLP-1(1-37) might activate the GLP-1R via a different mechanism. Therefore, our findings suggest that GLP-1(1-37) could be a potential therapeutic drug for the treatment of type 2 diabetes in the future.

3. GLP-1-related proteins attenuate the effects of mitochondrial membrane damage in pancreatic β cells

Risa Ide, Naoko Iwasaki, Miho Takizawa, Yasuko Uchigata, Makiko Ogata Biochem Biophys Res Commun . 2014 Apr 25;447(1):133-8. doi: 10.1016/j.bbrc.2014.03.143.

Glucagon-like peptide (GLP)-1 analog based therapies are used not only for their insulinotropic effects, but also for their pleiotropic effects that improve pancreatic β cell function. Liraglutide is a long acting derivative of human GLP-1(7-37), which is a cleavage product encompassing amino acids 7-37 of GLP-1. In this study, we examined whether Liraglutide treatment restore the glucose-stimulated mitochondrial response of β cells with chemically induced mitochondrial damage. We tested three GLP-1-related proteins: human GLP-1(1-37), GLP-1(7-37) and Liraglutide. To measure changes of the mitochondrial pH quantitatively in real-time, we have developed a bioengineered β cell line. We generated a mitochondrial damaged model by treating β cells with ethidium bromide (EtBr; 0.5 or 1 μg/mL for 48 h). EtBr treatment reduced the response to 25 mM glucose in mitochondrial pH in a dose- and time-dependent manner. GLP-1(7-37) (100 nM) enhanced the response of mitochondria to glucose stimulation in undamaged β cells. Preincubation with Liraglutide (1 nM) or GLP-1 (100 nM) for 3h recovered the mitochondrial response to glucose in damaged β cells, however, GLP-1(7-37) (100 nM) did not. When GLP-1(7-37) was administered in stepwise increments (i.e., starting with 20 nM to reach 100 nM in 3h), similar recovery of the mitochondrial function was observed. The results suggest that Liraglutide is effective to recover glucose-stimulated mitochondrial response in damaged β cells.

Eyeliss

CAT NO. : BAT-006233

Azido-PEG4-alcohol

CAT NO. : BAT-001233

Myristoyl tripeptide-31

CAT NO. : BAT-006235

Hexapeptide-3

CAT NO. : BAT-006157

Decapeptide-12

CAT NO. : BAT-006156

Neuropeptide Y (29-64)

CAT NO. : BAT-009963