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E7144

Sigma-Aldrich

Exendin-4

≥97%

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About This Item

Empirical Formula (Hill Notation):
C184H282N50O60S
CAS Number:
Molecular Weight:
4186.57
MDL number:
UNSPSC Code:
51111800
NACRES:
NA.32
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Quality Level

Assay

≥97%

storage temp.

−20°C

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

Gene Information

human ... GLP1R(2740)

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Amino Acid Sequence

His-Gly-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Leu-Ser-Lys-Gln-Met-Glu-Glu-Glu-Ala-Val-Arg-Leu-Phe-Ile-Glu-Trp-Leu-Lys-Asn-Gly-Gly-Pro-Ser-Ser-Gly-Ala-Pro-Pro-Pro-Ser-NH2

General description

Exendin-4 is an incretin mimetic peptide, which is composed of 39 amino acids.[1] It is an analog of glucagon-like peptide 1 (GLP-1), and an insulinotropic agent, with a long half-life.[2] Exendin-4 was historically isolated from the venom of Gila monster lizard called Heloderma suspectum.[3]

Application

Exendin-4 has been used as incretin mimetics for the treatment in HepG2 cells to exclude the influence of auxiliary material.[4] It has also been used as an r (GLP-1R) agonist to exclude interference from auxiliary material.[5]
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),[6] and for the determination of nuclear factor-κΒ (NF-κB) p65 level in macrophages treated with exendin-4.[7]

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.[1] It promotes the neogeneration and proliferation of β-cells, and thus aids in the regeneration of pancreas.[2] It acts as a ligand to exendin receptor, and leads to an elevation of acinar cell cAMP levels.[3]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Synthetically produced
Lyophilized from 0.1% TFA in H2O

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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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
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
GLP-1 receptor agonist promotes brown remodelling in mouse white adipose tissue through SIRT1
Xu F, et al.
Diabetologia, 59(5), 1059-1069 (2016)
Anujith Kumar et al.
PloS one, 8(5), e63491-e63491 (2013-05-15)
β-cell replacement may efficiently cure type 1 diabetic (T1D) patients whose insulin-secreting β-cells have been selectively destroyed by autoantigen-reactive T cells. To generate insulin-secreting cells we used two cell sources: rat multipotent adult progenitor cells (rMAPC) and the highly similar
G Singh et al.
Regulatory peptides, 53(1), 47-59 (1994-08-31)
We synthesized and iodinated an exendin-4 analogue, [Y39]exendin-4 (700 Ci/mmol), for use as a radioligand to characterize exendin receptors on dispersed pancreatic acini and gastric chief cells from guinea pig. Binding of this bioactive radioligand was rapid, temperature-dependent and specific

Questions

1–6 of 6 Questions  
  1. At what temperature and for how long can exendin-4 be stored after reconstituted?

    1 answer
    1. The stability of this material in solution has not been determined. However, various sources report that stock solutions are stable refrigerated for 2-7 days. For long term solution storage, single use aliquots containing 0.1% BSA or HSA may be stored at -20°C. This information has not been validated.

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  2. I would like to ask if it can be diluted in water only without 0.1% TFA

    1 answer
    1. The product was lyophilized from a solution containing 0.1% TFA in H2O. It is soluble in water at 1.00 - 1.04 mg/mL. Please see the link below to review a sample Certificate of Analysis:
      https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/E7144-0.5MG-PW0000191855.pdf

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

    1 answer
    1. 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.

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

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

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

    1 answer
    1. 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.

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

    1 answer
    1. Trifluoroacetate is the counterion present.

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