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Amylin (8-37), rat

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Amylin (8-37), rat is a truncated natural Amylin analogue that selectively inhibits insulin-related glucose uptake and glycogen deposition in muscle tissue.

Category

Peptide Inhibitors

Catalog number

BAT-010437

CAS number

138398-61-5

Molecular Formula

C140H227N43O43

Molecular Weight

3200.61

Specification
Reference Reading

IUPAC Name

(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-4-amino-1-[[(2S)-1-[[2-[(2S)-2-[[(2S)-1-[[(2S)-1-[(2S)-2-[(2S)-2-[[(2S,3R)-1-[[(2S)-4-amino-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]carbamoyl]pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-2-oxoethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]-2-[[(2S,3R)-2-[[(2S)-2-aminopropanoyl]amino]-3-hydroxybutanoyl]amino]pentanediamide

Synonyms

Amylin (8-37) (mouse, rat); H-Ala-Thr-Gln-Arg-Leu-Ala-Asn-Phe-Leu-Val-Arg-Ser-Ser-Asn-Asn-Leu-Gly-Pro-Val-Leu-Pro-Pro-Thr-Asn-Val-Gly-Ser-Asn-Thr-Tyr-NH2; L-alanyl-L-threonyl-L-glutaminyl-L-arginyl-L-leucyl-L-alanyl-L-asparagyl-L-phenylalanyl-L-leucyl-L-valyl-L-arginyl-L-seryl-L-seryl-L-asparagyl-L-asparagyl-L-leucyl-glycyl-L-prolyl-L-valyl-L-leucyl-L-prolyl-L-prolyl-L-threonyl-L-asparagyl-L-valyl-glycyl-L-seryl-L-asparagyl-L-threonyl-L-tyrosinamide

Appearance

Lyophilized Powder

Purity

≥95%

Density

1.51±0.1 g/cm3 (Predicted)

Sequence

ATQRLANFLVRSSNNLGPVLPPTNVGSNTY-NH2

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C140H227N43O43/c1-62(2)46-81(114(202)156-58-104(198)181-43-25-32-94(181)129(217)177-107(68(13)14)133(221)172-90(49-65(7)8)137(225)183-45-27-34-96(183)138(226)182-44-26-33-95(182)130(218)180-110(73(19)189)136(224)171-89(56-102(147)196)124(212)175-105(66(9)10)131(219)155-57-103(197)158-91(59-184)126(214)170-88(55-101(146)195)125(213)179-109(72(18)188)135(223)162-80(111(148)199)50-75-35-37-76(190)38-36-75)164-121(209)86(53-99(144)193)168-122(210)87(54-100(145)194)169-127(215)92(60-185)174-128(216)93(61-186)173-116(204)78(31-24-42-154-140(151)152)160-132(220)106(67(11)12)176-123(211)83(48-64(5)6)166-119(207)84(51-74-28-21-20-22-29-74)167-120(208)85(52-98(143)192)163-113(201)70(16)157-118(206)82(47-63(3)4)165-115(203)77(30-23-41-153-139(149)150)159-117(205)79(39-40-97(142)191)161-134(222)108(71(17)187)178-112(200)69(15)141/h20-22,28-29,35-38,62-73,77-96,105-110,184-190H,23-27,30-34,39-61,141H2,1-19H3,(H2,142,191)(H2,143,192)(H2,144,193)(H2,145,194)(H2,146,195)(H2,147,196)(H2,148,199)(H,155,219)(H,156,202)(H,157,206)(H,158,197)(H,159,205)(H,160,220)(H,161,222)(H,162,223)(H,163,201)(H,164,209)(H,165,203)(H,166,207)(H,167,208)(H,168,210)(H,169,215)(H,170,214)(H,171,224)(H,172,221)(H,173,204)(H,174,216)(H,175,212)(H,176,211)(H,177,217)(H,178,200)(H,179,213)(H,180,218)(H4,149,150,153)(H4,151,152,154)/t69-,70-,71+,72+,73+,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,105-,106-,107-,108-,109-,110-/m0/s1

InChI Key

KXIRMGRGEHRNNC-ANJGTFPLSA-N

Canonical SMILES

CC(C)CC(C(=O)NC(C)C(=O)NC(CC(=O)N)C(=O)NC(CC1=CC=CC=C1)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CO)C(=O)NC(CO)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)N)C(=O)NC(CC(C)C)C(=O)NCC(=O)N2CCCC2C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)N3CCCC3C(=O)N4CCCC4C(=O)NC(C(C)O)C(=O)NC(CC(=O)N)C(=O)NC(C(C)C)C(=O)NCC(=O)NC(CO)C(=O)NC(CC(=O)N)C(=O)NC(C(C)O)C(=O)NC(CC5=CC=C(C=C5)O)C(=O)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCC(=O)N)NC(=O)C(C(C)O)NC(=O)C(C)N

1. Amylin or CGRP (8-37) fragments reverse amylin-induced inhibition of 14C-glycogen accumulation

R O Deems, F Cardinaux, R W Deacon, D A Young Biochem Biophys Res Commun. 1991 Nov 27;181(1):116-20. doi: 10.1016/s0006-291x(05)81389-0.

The peptides amylin and calcitonin-gene related peptide (CGRP) have been shown to have similar effects on glycogen metabolism in vivo and in vitro. However, it is not clear whether they act via separate receptors. Peptide fragments based on the amino acid sequence of amylin or CGRP were evaluated for their ability to inhibit the action of the peptides in vitro. Insulin-stimulated glycogen turnover, as measured by 14C-glycogen accumulation, was inhibited about 70% by amylin (10nM) and 85% by CGRP (10nM). In the absence of exogenous peptide, peptide fragments based on the 8-37 and 10-37 amino acid sequences of rat amylin (10 uM) had no affect on 14C-glycogen accumulation. In the presence of amylin (10nM), the 8-37 and 10-37 fragments blocked amylin-induced inhibition of 14C-glycogen accumulation 100% and 11.4%, respectively. The 8-37 and 10-37 amylin fragments blocked CGRP inhibition of 14C-glycogen accumulation by 23.2% or 28.6%, respectively. The CGRP 8-37 fragment was equally effective as the amylin 8-37 reversing the effects of amylin than at reversing the effects of CGRP. These results demonstrate that amylin (8-37) completely antagonizes the effects of amylin with limited ability to block CGRP. Removing the eighth and ninth amino acids reduced the effectiveness of the inhibitor by about 90%.

2. Rat amylin-(8-37) enhances insulin action and alters lipid metabolism in normal and insulin-resistant rats

M Hettiarachchi, S Chalkley, S M Furler, Y S Choong, M Heller, G J Cooper, E W Kraegen Am J Physiol. 1997 Nov;273(5):E859-67. doi: 10.1152/ajpendo.1997.273.5.E859.

To clarify roles of amylin, we investigated metabolic responses to rat amylin-(8-37), a specific amylin antagonist, in normal and insulin-resistant, human growth hormone (hGH)-infused rats. Fasting conscious rats were infused with saline or hGH, each with and without amylin-(8-37) (0.125 mumol/h), over 5.75 h. At 3.75 h, a hyperinsulinemic (100 mU/l) clamp with bolus 2-deoxy-D-[3H]glucose and [14C]glucose was started. hGH infusion led to prompt (2- to 3-fold) basal hyperamylinemia (P < 0.02) and hyperinsulinemia. Amylin-(8-37) reduced plasma insulin (P < 0.001) and enhanced several measures of whole body and muscle insulin sensitivity (P < 0.05) in both saline- and hGH-infused rats. Amylin-(8-37) corrected hGH-induced liver insulin resistance, increased basal plasma triglycerides and lowered plasma nonesterified fatty acids in both groups, and reduced muscle triglyceride and total long-chain acyl-CoA content in saline-treated rats (P < 0.05). In isolated soleus muscle, amylin-(8-37) blocked amylin-induced inhibition of glycogen synthesis but had no effect in the absence of amylin. Thus 1) hyperamylinemia accompanies insulin resistance induced by hGH infusion; 2) amylin-(8-37) increases whole body and muscle insulin sensitivity and consistently reduces basal insulin levels in normal and hGH-induced insulin resistant rats; and 3) amylin-(8-37) elicits a significant alteration of in vivo lipid metabolism. These findings support a role of amylin in modulating insulin action and suggest that this could be mediated by effects on lipid metabolism.

3. The effect of adrenomedullin, amylin fragment 8-37 and calcitonin gene-related peptide on contractile force, heart rate and coronary perfusion pressure in isolated rat hearts

Z Kaygisiz, N Erksap, R Uyar, S Kabadere, T E Kabadere, S Dernek Acta Physiol Hung. 2003;90(2):133-46. doi: 10.1556/APhysiol.90.2003.2.6.

The effect of human adrenomedullin, human amylin fragment 8-37 (amylin 8-37) and rat calcitonin gene-related peptide (CGRP) on contractile force, heart rate and coronary perfusion pressure has been investigated in the isolated perfused rat hearts. Adrenomedullin (2x10(-10), 2x10(-9) and 2x10(-8) M) produced a significant decrease in contractile force and perfusion pressure, but only the peptide caused a decline in heart rate at the highest dose. Amylin (10(-9), 10(-8) and 10(-7) M) significantly increased and then decreased contractile force. Two doses of amylin (10(-8) and 10(-7) M) induced a significant increase in heart rate, however amylin did not change perfusion pressure in all the doses used. Rat alpha CGRP (10(-8), 10(-7) and 10(-6) M) evoked a slight decline in contractile force following a significant increase in contractile force induced by the peptide. CGRP in all the doses raised heart rate and lowered perfusion pressure. Our results suggest that adrenomedullin has negative inotropic, negative chronotropic and coronary vasodilator actions. Amylin produces a biphasic inotropic effect and evokes a positive chronotropy. CGRP causes positive inotropic, positive chronotropic and vasodilatory effects in isolated rat hearts.