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CGRP (rat)

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α-CGRP (rat) is an endogenous neuropeptide displaying vasodilator, cardiovascular, pro-inflammatory and metabolic effects.

Category

Peptide Inhibitors

Catalog number

BAT-010184

CAS number

83651-90-5

Molecular Formula

C162H262N50O52S2

Molecular Weight

3806.3

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-[[(4R,7S,10S,13S,16S,19R)-19-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-16-(2-amino-2-oxoethyl)-7,13-bis[(1R)-1-hydroxyethyl]-10-methyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]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 (rat)

Appearance

Powder

Purity

>95%

Sequence

SC(1)NTATC(1)VTHRLAGLLSRSGGVVKDNFVPTNVGSEAF

Storage

Store at -20°C

InChI

InChI=1S/C162H262N50O52S2/c1-71(2)49-95(184-114(225)62-177-129(233)79(17)181-138(242)96(50-72(3)4)191-136(240)91(40-32-46-174-161(169)170)186-141(245)99(54-88-59-173-70-180-88)197-158(262)127(85(23)220)211-155(259)122(77(13)14)205-150(254)108-69-266-265-68-107(201-132(236)89(164)64-213)149(253)195-101(56-111(166)222)146(250)209-124(82(20)217)156(260)183-81(19)131(235)208-125(83(21)218)159(263)202-108)139(243)192-97(51-73(5)6)140(244)200-106(67-216)148(252)187-92(41-33-47-175-162(171)172)137(241)199-104(65-214)133(237)178-60-113(224)176-61-116(227)203-120(75(9)10)154(258)206-121(76(11)12)153(257)189-90(39-30-31-45-163)135(239)196-103(58-118(230)231)143(247)194-100(55-110(165)221)142(246)193-98(53-87-37-28-25-29-38-87)144(248)207-123(78(15)16)160(264)212-48-34-42-109(212)151(255)210-126(84(22)219)157(261)198-102(57-112(167)223)145(249)204-119(74(7)8)152(256)179-63-115(226)185-105(66-215)147(251)188-93(43-44-117(228)229)134(238)182-80(18)130(234)190-94(128(168)232)52-86-35-26-24-27-36-86/h24-29,35-38,59,70-85,89-109,119-127,213-220H,30-34,39-58,60-69,163-164H2,1-23H3,(H2,165,221)(H2,166,222)(H2,167,223)(H2,168,232)(H,173,180)(H,176,224)(H,177,233)(H,178,237)(H,179,256)(H,181,242)(H,182,238)(H,183,260)(H,184,225)(H,185,226)(H,186,245)(H,187,252)(H,188,251)(H,189,257)(H,190,234)(H,191,240)(H,192,243)(H,193,246)(H,194,247)(H,195,253)(H,196,239)(H,197,262)(H,198,261)(H,199,241)(H,200,244)(H,201,236)(H,202,263)(H,203,227)(H,204,249)(H,205,254)(H,206,258)(H,207,248)(H,208,235)(H,209,250)(H,210,255)(H,211,259)(H,228,229)(H,230,231)(H4,169,170,174)(H4,171,172,175)/t79-,80-,81-,82+,83+,84+,85+,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,119-,120-,121-,122-,123-,124-,125-,126-,127-/m0/s1

InChI Key

SVAGNGUJZNLSEY-TYNJZYKVSA-N

Canonical SMILES

CC1C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)N1)C(C)O)CC(=O)N)NC(=O)C(CO)N)C(=O)NC(C(C)C)C(=O)NC(C(C)O)C(=O)NC(CC2=CNC=N2)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC(C)C)C(=O)NC(C)C(=O)NCC(=O)NC(CC(C)C)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(CC3=CC=CC=C3)C(=O)NC(C(C)C)C(=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(CCC(=O)O)C(=O)NC(C)C(=O)NC(CC5=CC=CC=C5)C(=O)N)C(C)O

1.Molecular anatomy of the neuro-immune connection.

Weihe E1, Nohr D, Michel S, Müller S, Zentel HJ, Fink T, Krekel J. Int J Neurosci. 1991 Jul;59(1-3):1-23.

Light microscopic immunohistochemistry was employed to elucidate and compare the presence, distribution, and coexistence of various peptides, neuroendocrine markers and enzymes of the catecholamine pathway in nerves supplying lymphoid tissues in a variety of mammalian species. All lymphoid organs and tissues receive innervation by fibers containing dopamine-beta-hydroxylase and/or tyrosine hydroxylase, neural markers like protein gene product 9.5, synaptophysin and neurofilament and a varied spectrum of peptides. The prominent peptides were tachykinins (substance P, neurokinin A), calcitonin gene-related peptide (CGRP), neuropeptide Y (NPY), and vasoactive intestinal polypeptide/peptide histidine isoleucine (VIP/PHI). Opioid innervation was variable. Double immunofluorescence revealed coexistence of tachykinins and CGRP and of tyrosine hydroxylase and NPY. A minor proportion of fibers showed coexistence of NPY and tachykinins and of VIP/PHI and tachykinins.

2.Coexpression of receptors for adrenomedullin, calcitonin gene-related peptide, and amylin in pancreatic beta-cells.

Martínez A1, Kapas S, Miller MJ, Ward Y, Cuttitta F. Endocrinology. 2000 Jan;141(1):406-11.

Three receptors have been characterized by their ability to bind adrenomedullin (AM): L1, RDC1, and CRLR. Immunohistochemical analysis and RT-PCR showed that all three receptors are expressed by the insulin-producing cells of the islets of Langerhans. RDC1 and CRLR in the presence of particular modifying proteins can also bind calcitonin gene-related peptide (CGRP). Such data suggest that the inhibitory effect caused by both AM and CGRP on insulin secretion is mediated by a direct interaction with the beta-cell. We also identified receptors for amylin, the third member of the AM peptide family, in mouse insulin-secreting cells. The beta-cells located closer to the periphery of the islets had a stronger immunoreactivity for the AM/ CGRP receptors. This observation could be related to a paracrine mechanism, given the proximity of AM- and CGRP-secreting cells (F and delta-cells, respectively), which are located at the periphery of the islets.

3.Neurovascular aspects of skin neurogenic inflammation.

Aubdool AA1, Brain SD. J Investig Dermatol Symp Proc. 2011 Dec;15(1):33-9. doi: 10.1038/jidsymp.2011.8.

Neurogenic inflammation is involved in skin inflammation. It is hypothesized that it is involved in the pathogenesis of the common chronic cutaneous vascular disorder rosacea, but the exact mechanism of action is currently unknown. Transient receptor potential vanilloid 1 (TRPV1) and ankyrin 1 (TRPA1) are widely expressed on primary sensory neuron endings and non-neuronal cells such as keratinocytes. Here we describe the potential for TRPV1 and TRPA1 receptors to be involved in the pathophysiology of rosacea due to their polymodal activation, including cold and hot temperature, pungent products from vegetable and spices, reactive oxygen species, and mechanical stimuli. We discuss the role of both receptors and the sensory neuropeptides that they release in inflammation and pain sensation and evidence suggesting that both TRPV1 and TRPA1 receptors may be promising therapeutic targets for the treatment of the inflammatory symptoms of rosacea.

4.Trifluoroacetate, a contaminant in purified proteins, inhibits proliferation of osteoblasts and chondrocytes.

Cornish J1, Callon KE, Lin CQ, Xiao CL, Mulvey TB, Cooper GJ, Reid IR. Am J Physiol. 1999 Nov;277(5 Pt 1):E779-83.

Peptides purified by HPLC are often in the form of a trifluoroacetate (TFA) salt, because trifluoroacetic acid is used as a solvent in reversed-phase HPLC separation. However, the potential effects of this contaminant in culture systems have not been addressed previously. TFA (10(-8) to 10(-7) M) reduced cell numbers and thymidine incorporation into fetal rat osteoblast cultures after 24 h. Similar effects were found in cultures of articular chondrocytes and neonatal mouse calvariae, indicating that the effect is not specific to one cell type or to one species of origin. When the activities of the TFA and hydrochloride salts of amylin, amylin-(1-8), and calcitonin were compared in osteoblasts, cell proliferation was consistently less with the TFA salts of these peptides, resulting in failure to detect a proliferative effect or wrongly attributing an antiproliferative effect. This finding is likely to be relevant to all studies of purified peptides in concentrations above 10(-9) M in whatever cell or tissue type.