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Rat CGRP-(8-37)

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CGRP 8-37 (rat) is a peptide antagonist for CGRP1 receptors.

Category

Peptide Inhibitors

Catalog number

BAT-010616

CAS number

129121-73-9

Molecular Formula

C138H224N42O41

Molecular Weight

3127.51

Specification
Reference Reading

IUPAC Name

(4S)-4-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S,3R)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxypropanoyl]amino]acetyl]amino]acetyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]hexanoyl]amino]-3-carboxypropanoyl]amino]-4-oxobutanoyl]amino]-3-phenylpropanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoyl]amino]-4-oxobutanoyl]amino]-3-methylbutanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-5-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

Synonyms

Calcitonin Gene-Related Peptide 8-37 (rat); 8-37-a-Calcitoningene-related peptide (human reduced), 25-L-aspartic acid, 35-L-glutamic acid-; Val-Thr-His-Arg-Leu-Ala-Gly-Leu-Leu-Ser-Arg-Ser-Gly-Gly-Val-Val-Lys-Asp-Asn-Phe-Val-Pro-Thr-Asn-Val-Gly-Ser-Glu-Ala-Phe-NH2; CGRP 8-37 rat; L-valyl-L-threonyl-L-histidyl-L-arginyl-L-leucyl-L-alanyl-glycyl-L-leucyl-L-leucyl-L-seryl-L-arginyl-L-seryl-glycyl-glycyl-L-valyl-L-valyl-L-lysyl-L-alpha-aspartyl-L-asparagyl-L-phenylalanyl-L-valyl-L-prolyl-L-threonyl-L-asparagyl-L-valyl-glycyl-L-seryl-L-alpha-glutamyl-L-alanyl-L-phenylalaninamide

Appearance

White or Off-white Lyophilized Powder

Purity

≥95%

Density

1.5±0.1 g/cm3

Sequence

VTHRLAGLLSRSGGVVKDNFVPTNVGSEAF-NH2

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C138H224N42O41/c1-64(2)46-84(158-99(189)58-152-112(197)72(17)156-119(204)85(47-65(3)4)165-117(202)80(37-29-43-149-137(144)145)160-122(207)88(51-78-55-148-63-155-78)170-135(220)110(75(20)185)179-130(215)104(142)67(7)8)120(205)166-86(48-66(5)6)121(206)173-94(62-183)128(213)161-81(38-30-44-150-138(146)147)118(203)172-92(60-181)114(199)153-56-98(188)151-57-101(191)174-106(69(11)12)133(218)176-107(70(13)14)132(217)163-79(36-27-28-42-139)116(201)169-91(54-103(194)195)124(209)168-89(52-96(140)186)123(208)167-87(50-77-34-25-22-26-35-77)125(210)177-108(71(15)16)136(221)180-45-31-39-95(180)129(214)178-109(74(19)184)134(219)171-90(53-97(141)187)126(211)175-105(68(9)10)131(216)154-59-100(190)159-93(61-182)127(212)162-82(40-41-102(192)193)115(200)157-73(18)113(198)164-83(111(143)196)49-76-32-23-21-24-33-76/h21-26,32-35,55,63-75,79-95,104-110,181-185H,27-31,36-54,56-62,139,142H2,1-20H3,(H2,140,186)(H2,141,187)(H2,143,196)(H,148,155)(H,151,188)(H,152,197)(H,153,199)(H,154,216)(H,156,204)(H,157,200)(H,158,189)(H,159,190)(H,160,207)(H,161,213)(H,162,212)(H,163,217)(H,164,198)(H,165,202)(H,166,205)(H,167,208)(H,168,209)(H,169,201)(H,170,220)(H,171,219)(H,172,203)(H,173,206)(H,174,191)(H,175,211)(H,176,218)(H,177,210)(H,178,214)(H,179,215)(H,192,193)(H,194,195)(H4,144,145,149)(H4,146,147,150)/t72-,73-,74+,75+,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,104-,105-,106-,107-,108-,109-,110-/m0/s1

InChI Key

HZKKKBMPFPSSKZ-QZMRZBIOSA-N

Canonical SMILES

CC(C)CC(C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(CCCNC(=N)N)C(=O)NC(CO)C(=O)NCC(=O)NCC(=O)NC(C(C)C)C(=O)NC(C(C)C)C(=O)NC(CCCCN)C(=O)NC(CC(=O)O)C(=O)NC(CC(=O)N)C(=O)NC(CC1=CC=CC=C1)C(=O)NC(C(C)C)C(=O)N2CCCC2C(=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(CCC(=O)O)C(=O)NC(C)C(=O)NC(CC3=CC=CC=C3)C(=O)N)NC(=O)CNC(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC4=CNC=N4)NC(=O)C(C(C)O)NC(=O)C(C(C)C)N

1. Inhibitory effect of BIBN4096BS, CGRP(8-37), a CGRP antibody and an RNA-Spiegelmer on CGRP induced vasodilatation in the perfused and non-perfused rat middle cerebral artery

L Edvinsson, E Nilsson, I Jansen-Olesen Br J Pharmacol. 2007 Mar;150(5):633-40. doi: 10.1038/sj.bjp.0707134. Epub 2007 Jan 22.

Background and purpose: A new concept for the inhibition of CGRP signalling has been developed by interaction with the CGRP molecule per se by using a CGRP antibody or a CGRP binding RNA-Spiegelmer (NOX-C89). We have compared these CGRP scavengers with two known receptor antagonists (CGRP8-37 and BIBN4096BS) on CGRP-induced relaxations in the rat middle cerebral artery (MCA). Furthermore, the role of the endothelial barrier has been studied. Experimental approach: We used the luminally perfused MCA in an arteriograph, pressurized to 85 mm Hg and myograph studies of isolated ring segments of the MCA. Key results: In myograph studies and in the perfusion system during abluminal application, alphaCGRP and betaCGRP induced concentration-dependent dilatation of the MCA. Given luminally neither peptide was significantly vasodilator. Adrenomedullin and amylin induced weak dilatations. In myograph experiments, relaxation induced by alphaCGRP was prevented by the four CGRP blockers (CGRP8-37, BIBN4096BS, the CGRP antibody and NOX-C89.). In abluminal perfusion experiments, the relaxant response to alphaCGRP was prevented by these agents to a varying degree. Dilatation induced by abluminal application of alphaCGRP was inhibited by luminal CGRP8-37 but not by luminal BIBN4096BS, CGRP antibody or NOX-C89. Conclusions and implications: alpha or betaCGRP acted on smooth muscle cell CGRP receptors in rat MCA and were effectively prevented from reaching these receptors by the endothelial barrier. The CGRP blockers significantly inhibited alphaCGRP induced relaxation but were also prevented from reaching the CGRP receptors by the arterial endothelium.

2. Bioactive beta-bend structures for the antagonist halpha CGRP(8 - 37) at the CGRP(1) receptor of the rat pulmonary artery

F M Wisskirchen, P M Doyle, S L Gough, C J Harris, I Marshall Br J Pharmacol. 2000 Mar;129(5):1049-55. doi: 10.1038/sj.bjp.0703152.

The aim of this study was to determine beta-bend structures and the role of the N- and C-terminus in the antagonist halpha CGRP(8 - 37) at the rat pulmonary artery CGRP receptor mediating halpha CGRP relaxation. Halpha CGRP(8 - 37) Pro(16) (10(-6) M), with a bend-biasing residue (proline) at position 16, did not antagonize halpha CGRP responses, while a structure-conserving amino acid (alanine(16)) at the same position retained antagonist activity (apparent pK(B) 6.6+/-0.1; 10(-6) M). Halpha CGRP(8 - 37) Pro(19) (10(-6) M), with proline at position 19 was an antagonist (apparent pK(B) 6.9+/-0.1). Incorporation of a beta-bend forcing residue, BTD (beta-turn dipeptide), at positions 19 and 20 in halpha CGRP(8 - 37) (10(-6) M) antagonized halpha CGRP responses (apparent pK(B) 7.2+/-0.2); and BTD at positions 19,20 and 33,34 within halpha CGRP(8 - 37) was a competitive antagonist (pA(2) 7.2; Schild plot slope 1.0+/-0.1). Halpha CGRP(8 - 37) analogues, substituted at the N-terminus by either glycine(8) or des-NH(2) valine(8) or proline(8) were all antagonists (apparent pK(B) 6.9+/-0.1; (10(-6) M), 7.0+/-0.1 (10(-6) M), and pA(2) 7.0 (slope 1.0+/-0.2), respectively); while replacements by proline(8) together with glutamic acid(10,14) in halpha CGRP(8 - 37) (10(-6) M) or alanine amide(37) at the C-terminus of halpha CGRP(8 - 37) (10(-5) M) were both inactive compounds. In conclusion, possible bioactive structures of halpha CGRP(8 - 37) include two beta-bends (at 18 - 21 and 32 - 35), which were mimicked by BTD incorporation. Within halpha CGRP(8 - 37), the N-terminus is not essential for antagonism while the C-terminus may interact directly with CGRP(1) receptors in the rat pulmonary artery.

3. A comparison of the actions of BIBN4096BS and CGRP(8-37) on CGRP and adrenomedullin receptors expressed on SK-N-MC, L6, Col 29 and Rat 2 cells

Debbie L Hay, Stephen G Howitt, Alex C Conner, Henri Doods, Marcus Schindler, David R Poyner Br J Pharmacol. 2002 Sep;137(1):80-6. doi: 10.1038/sj.bjp.0704844.

1. The ability of the CGRP antagonist BIBN4096BS to antagonize CGRP and adrenomedullin has been investigated on cell lines endogenously expressing receptors of known composition. 2. On human SK-N-MC cells (expressing human calcitonin receptor-like receptor (CRLR) and receptor activity modifying protein 1 (RAMP1)), BIBN4096BS had a pA(2) of 9.95 although the slope of the Schild plot (1.37 +/- 0.16) was significantly greater than 1. 3. On rat L6 cells (expressing rat CRLR and RAMP1), BIBN4096BS had a pA(2) of 9.25 and a Schild slope of 0.89 +/- 0.05, significantly less than 1. 4. On human Colony (Col) 29 cells, CGRP(8-37) had a significantly lower pA(2) than on SK-N-MC cells (7.34 +/- 0.19 (n = 7) compared to 8.35 +/- 0.18, (n = 6)). BIBN4096BS had a pA(2) of 9.98 and a Schild plot slope of 0.86 +/- 0.19 that was not significantly different from 1. At concentrations in excess of 3 nM, it was less potent on Col 29 cells than on SK-N-MC cells. 5. On Rat 2 cells, expressing rat CRLR and RAMP2, BIBN4096BS was unable to antagonize adrenomedullin at concentrations up to 10 microM. CGRP(8-37) had a pA(2) of 6.72 against adrenomedullin. 6. BIBN4096BS shows selectivity for the human CRLR/RAMP1 combination compared to the rat counterpart. It can discriminate between the CRLR/RAMP1 receptor expressed on SK-N-MC cells and the CGRP-responsive receptor expressed by the Col 29 cells used in this study. Its slow kinetics may explain its apparent 'non-competitive' behaviour. At concentrations of up to 10 micro M, it has no antagonist actions at the adrenomedullin, CRLR/RAMP2 receptor, unlike CGRP(8-37).