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Merck

E7144

Exendin-4

≥97%

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About This Item

Fórmula empírica (notación de Hill):
C184H282N50O60S
Número CAS:
141758-74-9
Peso molecular:
4186.57
UNSPSC Code:
51111800
NACRES:
NA.32
MDL number:
MFCD00240171

Nombre del producto

Exendin-4, ≥97%

SMILES string

S(CC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](N)Cc9[nH]cnc9)CCC(=O)O)[C@H](O)C)Cc8ccccc8)[C@H](O)C)CO)CC(=O)O)CC(C)C)CO)CCCCN)CCC(=O)N

InChI

1S/C184H282N50O60S/c1-16-94(10)147(178(289)213-114(52-58-144(257)258)163(274)218-121(73-101-77-195-105-39-24-23-38-103(101)105)168(279)215-116(68-90(2)3)165(276)205-107(41-26-28-61-186)158(269)219-122(75-134(189)243)154(265)198-79-135(244)196-83-139(248)231-63-30-43-129(231)175(286)225-127(87-238)174(285)223-125(85-236)155(266)200-80-136(245)202-96(12)181(292)233-65-32-45-131(233)183(294)234-66-33-46-132(234)182(293)232-64-31-44-130(232)176(287)222-124(84-235)150(190)261)229-170(281)119(71-99-34-19-17-20-35-99)217-166(277)117(69-91(4)5)214-159(270)108(42-29-62-194-184(191)192)212-177(288)146(93(8)9)228-151(262)95(11)203-156(267)111(49-55-141(251)252)208-161(272)112(50-56-142(253)254)209-162(273)113(51-57-143(255)256)210-164(275)115(59-67-295-15)211-160(271)110(47-53-133(188)242)207-157(268)106(40-25-27-60-185)206-172(283)126(86-237)224-167(278)118(70-92(6)7)216-169(280)123(76-145(259)260)220-173(284)128(88-239)226-180(291)149(98(14)241)230-171(282)120(72-100-36-21-18-22-37-100)221-179(290)148(97(13)240)227-138(247)82-199-153(264)109(48-54-140(249)250)204-137(246)81-197-152(263)104(187)74-102-78-193-89-201-102/h17-24,34-39,77-78,89-98,104,106-132,146-149,195,235-241H,16,25-33,40-76,79-88,185-187H2,1-15H3,(H2,188,242)(H2,189,243)(H2,190,261)(H,193,201)(H,196,244)(H,197,263)(H,198,265)(H,199,264)(H,200,266)(H,202,245)(H,203,267)(H,204,246)(H,205,276)(H,206,283)(H,207,268)(H,208,272)(H,209,273)(H,210,275)(H,211,271)(H,212,288)(H,213,289)(H,214,270)(H,215,279)(H,216,280)(H,217,277)(H,218,274)(H,219,269)(H,220,284)(H,221,290)(H,222,287)(H,223,285)(H,224,278)(H,225,286)(H,226,291)(H,227,247)(H,228,262)(H,229,281)(H,230,282)(H,249,250)(H,251,252)(H,253,254)(H,255,256)(H,257,258)(H,259,260)(H4,191,192,194)/t94-,95-,96-,97+,98+,104-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,146-,147-,148-,149-/m0/s1

InChI key

HTQBXNHDCUEHJF-XWLPCZSASA-N

assay

≥97%

storage temp.

−20°C

Quality Level

200

Gene Information

human ... GLP1R(2740)

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Application

Exendin-4 has been used as incretin mimetics for the treatment in HepG2 cells to exclude the influence of auxiliary material. It has also been used as an r (GLP-1R) agonist to exclude interference from auxiliary material.
Exendin-4 has been used for the treatment of ob/ob mouse model to determine the glucose and insulin concentrations and homeostasis model of assessment (HOMA), and for the determination of nuclear factor-κΒ (NF-κB) p65 level in macrophages treated with exendin-4.

Biochem/physiol Actions

Activates GLP-1 (glucagon-like peptide-1) receptors to increase intracellular cAMP in pancreatic acinar cells; has no effect on VIP receptors.
Exendin-4 mimics the activity of mammalian incretin hormone glucagon-like peptide 1 (GLP-1), and thus, functions in the control of glucose. This includes the secretion of insulin in a glucose dependent manner, negative regulation of high glucagon secretion, and increased duration of stomach emptying. In type 2 diabetes patients, this peptide can be administered subcutaneously for glycemic control, when metformin is unable to produce adequate results. It promotes the neogeneration and proliferation of β-cells, and thus aids in the regeneration of pancreas. It acts as a ligand to exendin receptor, and leads to an elevation of acinar cell cAMP levels.

General description

Exendin-4 is an incretin mimetic peptide, which is composed of 39 amino acids. It is an analog of glucagon-like peptide 1 (GLP-1), and an insulinotropic agent, with a long half-life. Exendin-4 was historically isolated from the venom of Gila monster lizard called Heloderma suspectum.

Other Notes

Lyophilized from 0.1% TFA in H2O
Synthetically produced

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000288947
0000288945
0000288947
0000288945
0000191855

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is Product E7144, Exendin-4, soluble in?

    Exendin-4 is soluble in water to a concentration of at least 1 mg/mL.

  4. What counterion is present in the Product E7144, Exendin-4, peptide preparation?

    Trifluoroacetate is the counterion present.

  5. What is the package size of Product E7144, Exendin-4, based on: total mass present or the mass of the peptide present?

    Since this is a trifluoroacetate salt of the peptide Exendin-4, the powder consists of the salt and peptide. The package size is based on the total mass present and not just the mass of the peptide. Please refer to lot-specific information on the certificate of analysis for the peptide content by amino acid analysis.

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

C Montrose-Rafizadeh et al.
The Journal of biological chemistry, 272(34), 21201-21206 (1997-08-22)
GLP-1-(7-36)-amide and exendin-4-(1-39) are glucagon-like peptide-1 (GLP-1) receptor agonists, whereas exendin-(9-39) is the only known antagonist. To analyze the transition from agonist to antagonist and to identify the amino acid residues involved in ligand activation of the GLP-1 receptor, we
Xiaokun Ding et al.
Hepatology (Baltimore, Md.), 43(1), 173-181 (2005-12-24)
Nonalcoholic fatty liver disease (NAFLD) represents a burgeoning problem in hepatology, and is associated with insulin resistance. Exendin-4 is a peptide agonist of the glucagon-like peptide (GLP) receptor that promotes insulin secretion. The aim of this study was to determine
Junling Liu et al.
EBioMedicine, 41, 73-84 (2019-03-05)
Glucagon-like peptide-1 (GLP-1) and its based agents improve glycemic control. Although their attenuating effect on hepatic glucose output has drawn our attention for decades, the potential mechanisms remain unclear. Cytokine array kit was used to assess cytokine profiles in db/db
Ralph A DeFronzo et al.
Diabetes care, 28(5), 1092-1100 (2005-04-28)
This study evaluates the ability of the incretin mimetic exenatide (exendin-4) to improve glycemic control in patients with type 2 diabetes failing to achieve glycemic control with maximally effective metformin doses. A triple-blind, placebo-controlled, 30-week study at 82 U.S. sites
GLP-1 receptor agonist promotes brown remodelling in mouse white adipose tissue through SIRT1
Xu F, et al.
Diabetologia, 59(5), 1059-1069 (2016)
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