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Secretin (28-54), human

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Secretin (human) is a gastrointestinal peptide hormone that stimulates pancreatic and biliary secretion. Secretin (human) is thought to play a role in the regulation of the hypothalamus-pituitary-adrenal axis.

Category

Peptide Inhibitors

Catalog number

BAT-010621

CAS number

108153-74-8

Molecular Formula

C130H220N44O40

Molecular Weight

3039.41

Specification
Reference Reading

IUPAC Name

(4S)-5-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[2-[[(2S)-1-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S,3R)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-4-carboxybutanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoic acid

Synonyms

Human secretin; Secretin (human); L-histidyl-L-seryl-L-alpha-aspartyl-glycyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-alpha-glutamyl-L-leucyl-L-seryl-L-arginyl-L-leucyl-L-arginyl-L-alpha-glutamyl-glycyl-L-alanyl-L-arginyl-L-leucyl-L-glutaminyl-L-arginyl-L-leucyl-L-leucyl-L-glutaminyl-glycyl-L-leucyl-L-valinamide; His-Ser-Asp-Gly-Thr-Phe-Thr-Ser-Glu-Leu-Ser-Arg-Leu-Arg-Glu-Gly-Ala-Arg-Leu-Gln-Arg-Leu-Leu-Gln-Gly-Leu-Val-NH2

Related CAS

121028-49-7 (rat)

Appearance

White or Off-white Lyophilized Powder

Purity

≥97% by HPLC

Density

1.49±0.1 g/cm3 (Predicted)

Sequence

HSDGTFTSELSRLREGARLQRLLQGLV-NH2

Storage

Store at -20°C

Solubility

Soluble in DMSO

InChI

InChI=1S/C130H220N44O40/c1-60(2)43-81(120(208)173-100(66(13)14)103(134)191)153-95(183)54-149-106(194)77(31-35-92(132)180)159-116(204)84(46-63(7)8)166-118(206)85(47-64(9)10)164-111(199)75(29-23-41-146-129(139)140)155-113(201)79(32-36-93(133)181)160-117(205)83(45-62(5)6)162-110(198)73(27-21-39-144-127(135)136)154-104(192)67(15)152-94(182)53-148-107(195)78(33-37-97(185)186)158-109(197)74(28-22-40-145-128(137)138)156-115(203)82(44-61(3)4)163-112(200)76(30-24-42-147-130(141)142)157-122(210)90(57-176)170-119(207)86(48-65(11)12)165-114(202)80(34-38-98(187)188)161-123(211)91(58-177)171-126(214)102(69(17)179)174-121(209)87(49-70-25-19-18-20-26-70)168-125(213)101(68(16)178)172-96(184)55-150-108(196)88(51-99(189)190)167-124(212)89(56-175)169-105(193)72(131)50-71-52-143-59-151-71/h18-20,25-26,52,59-69,72-91,100-102,175-179H,21-24,27-51,53-58,131H2,1-17H3,(H2,132,180)(H2,133,181)(H2,134,191)(H,143,151)(H,148,195)(H,149,194)(H,150,196)(H,152,182)(H,153,183)(H,154,192)(H,155,201)(H,156,203)(H,157,210)(H,158,197)(H,159,204)(H,160,205)(H,161,211)(H,162,198)(H,163,200)(H,164,199)(H,165,202)(H,166,206)(H,167,212)(H,168,213)(H,169,193)(H,170,207)(H,171,214)(H,172,184)(H,173,208)(H,174,209)(H,185,186)(H,187,188)(H,189,190)(H4,135,136,144)(H4,137,138,145)(H4,139,140,146)(H4,141,142,147)/t67-,68+,69+,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,100-,101-,102-/m0/s1

InChI Key

OWMZNFCDEHGFEP-NFBCVYDUSA-N

Canonical SMILES

CC(C)CC(C(=O)NC(C(C)C)C(=O)N)NC(=O)CNC(=O)C(CCC(=O)N)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(=O)N)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(C)NC(=O)CNC(=O)C(CCC(=O)O)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C(CC1=CC=CC=C1)NC(=O)C(C(C)O)NC(=O)CNC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(CC2=CNC=N2)N

1.Validation of SCT Methylation as a Hallmark Biomarker for Lung Cancers.

Zhang YA1, Ma X2, Sathe A3, Fujimoto J4, Wistuba II4, Lam S5, Yatabe Y6, Wang YW7, Stastny V7, Gao B7, Larsen JE7, Girard L7, Liu X7, Song K8, Behrens C4, Kalhor N9, Xie Y10, Zhang MQ11, Minna JD12, Gazdar AF13. J Thorac Oncol. 2016 Mar;11(3):346-60. doi: 10.1016/j.jtho.2015.11.004. Epub 2015 Dec 25.

INTRODUCTION: The human secretin gene (SCT) encodes secretin, a hormone with limited tissue distribution. Analysis of the 450k methylation array data in The Cancer Genome Atlas (TCGA) indicated that the SCT promoter region is differentially hypermethylated in lung cancer. Our purpose was to validate SCT methylation as a potential biomarker for lung cancer.

2.Dietary Lipids Inform the Gut and Brain about Meal Arrival via CD36-Mediated Signal Transduction.

Sundaresan S1, Abumrad NA2. J Nutr. 2015 Oct;145(10):2195-200. doi: 10.3945/jn.115.215483. Epub 2015 Aug 12.

Sensing mechanisms for nutrients, in particular dietary fat, operate in the mouth, brain, and gastrointestinal tract and play a key role in regulating feeding behavior and energy balance. Critical to these regulatory mechanisms are the specialized receptors present on taste buds on the tongue, on neurons in specialized centers in the brain, and on epithelial and enteroendocrine cells in the intestinal mucosa. These receptors recognize nutrients and respond by inducing intracellular signals that trigger release of bioactive compounds that influence other organs and help coordinate the response to the meal. Components of dietary fat that are recognized by these receptors are the long-chain fatty acids that act as ligands for 2 G protein-coupled receptors, GPR40 and GPR120, and the fatty acid (FA) translocase/CD36. Recent evidence that emphasizes the important role of CD36 in orosensory, intestinal, and neuronal sensing of FAs under physiologic conditions is highlighted in the review.

3.Diagnostic Performance of Contrast-Enhanced MRI With Secretin-Stimulated MRCP for Non-Calcific Chronic Pancreatitis: A Comparison With Histopathology.

Trikudanathan G1, Walker SP2, Munigala S3, Spilseth B4, Malli A5, Han Y6, Bellin M7, Chinnakotla S8, Dunn T8, Pruett TL8, Beilman GJ8, Vega Peralta J1, Arain MA1, Amateau SK1, Schwarzenberg SJ1, Mallery S1, Attam R1, Freeman ML1. Am J Gastroenterol. 2015 Nov;110(11):1598-606. doi: 10.1038/ajg.2015.297. Epub 2015 Sep 15.

OBJECTIVES: Diagnosis of non-calcific chronic pancreatitis (NCCP) in patients presenting with chronic abdominal pain is challenging and controversial. Contrast-enhanced magnetic resonance imaging (MRI) with secretin-stimulated MRCP (sMRCP) offers a safe and noninvasive modality to diagnose mild CP, but its findings have not been correlated with histopathology. We aimed to assess the correlation of a spectrum of MRI/sMRCP findings with surgical histopathology in a cohort of NCCP patients undergoing total pancreatectomy with islet autotransplantation (TPIAT).

4.C-terminal amidation of PACAP-38 and PACAP-27 is dispensable for biological activity at the PAC1 receptor.

Emery AC1, Alvarez RA1, Abboud P1, Xu W2, Westover CD2, Eiden MV2, Eiden LE3. Peptides. 2016 Mar 11;79:39-48. doi: 10.1016/j.peptides.2016.03.003. [Epub ahead of print]

PACAP-27 and PACAP-38 are the exclusive physiological ligands for the mammalian PAC1 receptor. The role of C-terminal amidation of these ligands at that receptor was examined in neuroendocrine cells expressing the PAC1 receptor endogenously and in non-neuroendocrine cells in which the human and rat PAC1 receptors were expressed from stable single-copy genes driven by the CMV promoter, providing stoichiometrically appropriate levels of this Gs-coupled GPCR in order to examine the potency and intrinsic activity of PACAP ligands and their des-amidated congeners. We found that replacement of the C-terminal glycine residues of PACAP-27 and -38 with a free acid; or extension of either peptide with the two to three amino acids normally found at these positions in PACAP processing intermediates in vivo following endoproteolytic cleavage and after exoproteolytic trimming and glycine-directed amidated, were equivalent in potency to the fully processed peptides in a variety of cell-based assays.