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Adrenomedullin (1-52), human

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Adrenomedullin is an antimicrobial peptide produced by adrenal medulla, skin, Homo sapiens (Human). It has antibacterial activity against Gram-positive and Gram-negative bacteria. In addition to controlling fluid-electrolyte homeostasis, adrenomedullin is an effective vasodilatory peptide hormone and can inhibit ACTH secretion of pituitary gland.

Category

Functional Peptides

Catalog number

BAT-010177

CAS number

148498-78-6

Molecular Formula

C264H406N80O77S3

Molecular Weight

6028.82

Specification
Reference Reading

IUPAC Name

(3S)-3-[[(2S)-6-amino-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S,3R)-2-[[(4R,7S,13S,16S,19R)-19-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-oxobutanoyl]amino]-4-oxobutanoyl]amino]-3-phenylpropanoyl]amino]-5-oxopentanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-phenylpropanoyl]amino]acetyl]amino]-13-benzyl-16-(3-carbamimidamidopropyl)-7-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]amino]-3-hydroxybutanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-carboxypropanoyl]amino]hexanoyl]amino]-4-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S,3S)-1-[[(2S)-1-[(2S)-2-[[(2S)-5-amino-1-[[2-[[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-1,5-dioxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-hydroxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-oxobutanoic acid

Synonyms

H-Tyr-Arg-Gln-Ser-Met-Asn-Asn-Phe-Gln-Gly-Leu-Arg-Ser-Phe-Gly-Cys(1)-Arg-Phe-Gly-Thr-Cys(1)-Thr-Val-Gln-Lys-Leu-Ala-His-Gln-Ile-Tyr-Gln-Phe-Thr-Asp-Lys-Asp-Lys-Asp-Asn-Val-Ala-Pro-Arg-Ser-Lys-Ile-Ser-Pro-Gln-Gly-Tyr-NH2; L-tyrosyl-L-arginyl-L-glutaminyl-L-seryl-L-methionyl-L-asparagyl-L-asparagyl-L-phenylalanyl-L-glutaminyl-glycyl-L-leucyl-L-arginyl-L-seryl-L-phenylalanyl-glycyl-L-cysteinyl-L-arginyl-L-phenylalanyl-glycyl-L-threonyl-L-cysteinyl-L-threonyl-L-valyl-L-glutaminyl-L-lysyl-L-leucyl-L-alanyl-L-histidyl-L-glutaminyl-L-isoleucyl-L-tyrosyl-L-glutaminyl-L-phenylalanyl-L-threonyl-L-alpha-aspartyl-L-lysyl-L-alpha-aspartyl-L-lysyl-L-alpha-aspartyl-L-asparagyl-L-valyl-L-alanyl-L-prolyl-L-arginyl-L-seryl-L-lysyl-L-isoleucyl-L-seryl-L-prolyl-L-glutaminyl-glycyl-L-tyrosinamide (16->21)-disulfide; Human adrenomedullin; Adrenomedullin (human); Human adrenomedullin-(1-52)-NH2

Related CAS

161383-47-7 (rat)

Appearance

White or Off-white Lyophilized Powder

Purity

>95%

Sequence

YRQSMNNFQGLRSFGCRFGTCTVQKLAHQIYQFTDKDKDNVAPRSKISPQGY-NH2 (Disulfide bridge: Cys16-Cys21)

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C264H406N80O77S3/c1-19-133(11)208(254(415)329-173(109-146-69-75-150(354)76-70-146)236(397)312-162(79-85-192(272)357)228(389)322-174(108-143-53-31-24-32-54-143)243(404)341-211(138(16)350)257(418)330-181(116-205(372)373)241(402)306-154(57-35-39-92-267)222(383)327-179(114-203(368)369)240(401)305-153(56-34-38-91-266)223(384)328-180(115-204(370)371)242(403)326-178(113-198(278)363)244(405)337-206(131(7)8)252(413)299-136(14)259(420)343-98-45-63-188(343)250(411)315-159(62-44-97-292-264(286)287)226(387)331-182(122-345)245(406)308-155(58-36-40-93-268)231(392)339-209(134(12)20-2)255(416)334-185(125-348)260(421)344-99-46-64-189(344)251(412)316-161(78-84-191(271)356)217(378)293-118-199(364)300-167(213(279)374)104-145-67-73-149(353)74-68-145)340-232(393)165(82-88-195(275)360)313-237(398)175(110-147-117-288-128-297-147)318-214(375)135(13)298-233(394)169(102-130(5)6)319-221(382)152(55-33-37-90-265)304-227(388)164(81-87-194(274)359)317-253(414)207(132(9)10)338-258(419)212(139(17)351)342-249(410)187-127-424-423-126-186(248(409)309-157(60-42-95-290-262(282)283)224(385)320-170(105-140-47-25-21-26-48-140)218(379)296-121-202(367)336-210(137(15)349)256(417)335-187)302-201(366)120-295-219(380)171(106-141-49-27-22-28-50-141)321-247(408)184(124-347)332-225(386)158(61-43-96-291-263(284)285)307-234(395)168(101-129(3)4)301-200(365)119-294-216(377)160(77-83-190(270)355)310-235(396)172(107-142-51-29-23-30-52-142)323-238(399)177(112-197(277)362)325-239(400)176(111-196(276)361)324-230(391)166(89-100-422-18)314-246(407)183(123-346)333-229(390)163(80-86-193(273)358)311-220(381)156(59-41-94-289-261(280)281)303-215(376)151(269)103-144-65-71-148(352)72-66-144/h21-32,47-54,65-76,117,128-139,151-189,206-212,345-354H,19-20,33-46,55-64,77-116,118-127,265-269H2,1-18H3,(H2,270,355)(H2,271,356)(H2,272,357)(H2,273,358)(H2,274,359)(H2,275,360)(H2,276,361)(H2,277,362)(H2,278,363)(H2,279,374)(H,288,297)(H,293,378)(H,294,377)(H,295,380)(H,296,379)(H,298,394)(H,299,413)(H,300,364)(H,301,365)(H,302,366)(H,303,376)(H,304,388)(H,305,401)(H,306,402)(H,307,395)(H,308,406)(H,309,409)(H,310,396)(H,311,381)(H,312,397)(H,313,398)(H,314,407)(H,315,411)(H,316,412)(H,317,414)(H,318,375)(H,319,382)(H,320,385)(H,321,408)(H,322,389)(H,323,399)(H,324,391)(H,325,400)(H,326,403)(H,327,383)(H,328,384)(H,329,415)(H,330,418)(H,331,387)(H,332,386)(H,333,390)(H,334,416)(H,335,417)(H,336,367)(H,337,405)(H,338,419)(H,339,392)(H,340,393)(H,341,404)(H,342,410)(H,368,369)(H,370,371)(H,372,373)(H4,280,281,289)(H4,282,283,290)(H4,284,285,291)(H4,286,287,292)/t133-,134-,135-,136-,137+,138+,139+,151-,152-,153-,154-,155-,156-,157-,158-,159-,160-,161-,162-,163-,164-,165-,166-,167-,168-,169-,170-,171-,172-,173-,174-,175-,176-,177-,178-,179-,180-,181-,182-,183-,184-,185-,186-,187-,188-,189-,206-,207-,208-,209-,210-,211-,212-/m0/s1

InChI Key

AEPFWOCREBHYQX-UUFXBYAOSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(CCC(=O)N)C(=O)NC(CC2=CC=CC=C2)C(=O)NC(C(C)O)C(=O)NC(CC(=O)O)C(=O)NC(CCCCN)C(=O)NC(CC(=O)O)C(=O)NC(CCCCN)C(=O)NC(CC(=O)O)C(=O)NC(CC(=O)N)C(=O)NC(C(C)C)C(=O)NC(C)C(=O)N3CCCC3C(=O)NC(CCCNC(=N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(CO)C(=O)N4CCCC4C(=O)NC(CCC(=O)N)C(=O)NCC(=O)NC(CC5=CC=C(C=C5)O)C(=O)N)NC(=O)C(CCC(=O)N)NC(=O)C(CC6=CNC=N6)NC(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C(CCCCN)NC(=O)C(CCC(=O)N)NC(=O)C(C(C)C)NC(=O)C(C(C)O)NC(=O)C7CSSCC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)N7)C(C)O)CC8=CC=CC=C8)CCCNC(=N)N)NC(=O)CNC(=O)C(CC9=CC=CC=C9)NC(=O)C(CO)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(CCC(=O)N)NC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)N)NC(=O)C(CC(=O)N)NC(=O)C(CCSC)NC(=O)C(CO)NC(=O)C(CCC(=O)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC1=CC=C(C=C1)O)N

1. Adrenomedullin in heart failure: pathophysiology and therapeutic application

Adriaan A Voors, Joachim Struck, Alexandre Mebazaa, Javed Butler, Hans-Dirk Düngen, Andreas Bergmann, Christopher Geven, Marco Metra, Daan Kremer, Peter Pickkers, Jozine M Ter Maaten Eur J Heart Fail . 2019 Feb;21(2):163-171. doi: 10.1002/ejhf.1366.

Adrenomedullin (ADM) is a peptide hormone first discovered in 1993 in pheochromocytoma. It is synthesized by endothelial and vascular smooth muscle cells and diffuses freely between blood and interstitium. Excretion of ADM is stimulated by volume overload to maintain endothelial barrier function. Disruption of the ADM system therefore results in vascular leakage and systemic and pulmonary oedema. In addition, ADM inhibits the renin-angiotensin-aldosterone system. ADM is strongly elevated in patients with sepsis and in patients with acute heart failure. Since hallmarks of both conditions are vascular leakage and tissue oedema, we hypothesize that ADM plays a compensatory role and may exert protective properties against fluid overload and tissue congestion. Recently, a new immunoassay that specifically measures the biologically active ADM (bio-ADM) has been developed, and might become a biomarker for tissue congestion. As a consequence, measurement of bio-ADM might potentially be used to guide diuretic therapy in patients with heart failure. In addition, ADM might be used to guide treatment of (pulmonary) oedema or even become a target for therapy. Adrecizumab is a humanized, monoclonal, non-neutralizing ADM-binding antibody with a half-life of 15 days. Adrecizumab binds at the N-terminal epitope of ADM, leaving the C-terminal side intact to bind to its receptor. Due to its high molecular weight, the antibody adrecizumab cannot cross the endothelial barrier and consequently remains in the circulation. The observation that adrecizumab increases plasma concentrations of ADM indicates that ADM-binding by adrecizumab is able to drain ADM from the interstitium into the circulation. We therefore hypothesize that administration of adrecizumab improves vascular integrity, leading to improvement of tissue congestion and thereby may improve clinical outcomes in patients with acute decompensated heart failure. A phase II study with adrecizumab in patients with sepsis is ongoing and a phase II study on the effects of adrecizumab in patients with acute decompensated heart failure with elevated ADM is currently in preparation.

2. Degradation of human adrenomedullin(1-52) by plasma membrane enzymes and identification of metabolites

T G Yandle, L K Lewis, M W Smith, M G Nicholls, A M Richards, S O Brennan Peptides . 1997;18(5):733-9. doi: 10.1016/s0196-9781(97)00005-3.

Very little is known about degradation or metabolism of adrenomedullin. To this end, we incubated adrenomedullin with ovine adrenal, kidney and lung plasma membrane preparations and showed the major degradation products were ADM(2-52) and ADM(8-52). Smaller amounts of ADM(26-52), (27-52), (28-52) and (33-52) were also produced. Degradation was inhibited by EDTA and 1,10 phenanthroline but not by phosphoramidon, leupeptin and pepstatin. The above data are consistent with initial hydrolysis adjacent to hydrophobic residues by a metalloprotease, generating ADM(8-52), (26-52) and (33-52), followed by an aminopeptidase action to produce ADM(2-52), (27-52) and (28-52). Improved understanding of the metabolism of ADM may have therapeutic implications, for example in the treatment of heart failure.

3. Synthetic human adrenomedullin and adrenomedullin 15-52 have potent short-lived vasodilator activity in the hindlimb vascular bed of the cat

D H Coy, D B McNamara, P J Kadowitz, J A Santiago, E A Garrison, W A Murphy, V L Ventura, K Bitar Life Sci . 1994;55(5):PL85-90. doi: 10.1016/0024-3205(94)00652-0.

Responses to synthetic human adrenomedullin, a novel hypotensive peptide isolated from human pheochromocytoma cells, and the carboxy terminal 15-52 amino acid fragment of adrenomedullin (ADM15-52) were investigated in the hindlimb vascular bed of the cat under constant flow conditions. Intraarterial injections of the peptides in doses of 0.01-0.3 nmol caused dose-related decreases in hindlimb perfusion pressure. When compared on a nmol basis, adrenomedullin and ADM15-52 were similar to bradykinin in vasodilator potency and were approximately 10 fold less potent than acetylcholine. The half-life of the vasodilator response to adrenomedullin and ADM15-52 ranged from 55 to 80 sec and was greater than the half-life of vasodilator responses to bradykinin in doses of 0.01-0.3 nmol and acetylcholine in doses of 0.01-0.3 nmol. The present data demonstrate that synthetic human adrenomedullin and ADM15-52 have potent but relatively short-lasting vasodilator activity in the hindlimb vascular bed of the cat. These data suggest that amino acid residues 15-52 of adrenomedullin are important for the expression of vasodilator activity in the hindlimb vascular bed of the cat.