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Maxadilan

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Maxadilan, a potent vasodilator isolated from the salivary glands of the sand fly Lutzomyia longipalpis, specifically and effectively activates the mammalian PAC1 receptor, one of the three receptors of PACAP.

Category

Peptide APIs

Catalog number

BAT-015381

CAS number

135374-80-0

Molecular Formula

C291H466N86O94S6

Molecular Weight

6865.82

Specification
Reference Reading

IUPAC Name

(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(1aS,3S,4aS,6S,7aS,9S,10aS,12S,15S,16aS,18S,21S,24S,27S,30S,33S,36S,39S,42S,45S,48S,51S,54S,57S,60S,63S,66S,69S,72S,75S,78S,81S,84S,87R,92R,95S,98S)-87-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(4R,7S,10S,13S,16R)-16-amino-13-(carboxymethyl)-7-[(1R)-1-hydroxyethyl]-10-methyl-6,9,12,15-tetraoxo-1,2-dithia-5,8,11,14-tetrazacycloheptadecane-4-carbonyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]propanoyl]amino]-3-methylpentanoyl]amino]-3-carboxypropanoyl]amino]-3-carboxypropanoyl]amino]-81,98-bis(4-aminobutyl)-10a,63-bis(2-amino-2-oxoethyl)-6,42,54,78,84-pentakis(3-amino-3-oxopropyl)-1a,27-dibenzyl-95-(2-carboxyethyl)-15-(carboxymethyl)-12,24,30,36,39,51-hexakis[(1R)-1-hydroxyethyl]-7a,9,21,48,66-pentakis(hydroxymethyl)-69,72-bis(1H-imidazol-5-ylmethyl)-33,75-dimethyl-3,57-bis(2-methylpropyl)-18-(2-methylsulfanylethyl)-a,2,3a,5,6a,8,9a,11,12a,14,15a,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,83,86,94,97-heptatriacontaoxo-4a,45,60-tri(propan-2-yl)-89,90-dithia-1,2a,4,5a,7,8a,10,11a,13,14a,16,19,22,25,28,31,34,37,40,43,46,49,52,55,58,61,64,67,70,73,76,79,82,85,93,96,99-heptatriacontazabicyclo[114.3.0]nonadecahectane-92-carbonyl]amino]-4-methylsulfanylbutanoyl]amino]-6-aminohexanoyl]amino]-5-amino-5-oxopentanoyl]amino]-6-aminohexanoyl]amino]-6-aminohexanoyl]amino]-6-aminohexanoyl]amino]-5-[[(2S)-1-[[(2S)-6-amino-1-[[(1S)-1-carboxyethyl]amino]-1-oxohexan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-5-oxopentanoic acid

Synonyms

H-Cys-Asp-Ala-Thr-Cys-Gln-Phe-Arg-Lys-Ala-Ile-Asp-Asp-Cys-Gln-Lys-Gln-Ala-His-His-Ser-Asn-Val-Leu-Gln-Thr-Ser-Val-Gln-Thr-Thr-Ala-Thr-Phe-Thr-Ser-Met-Asp-Thr-Ser-Gln-Leu-Pro-Gly-Asn-Ser-Val-Phe-Lys-Glu-Cys-Met-Lys-Gln-Lys-Lys-Lys-Glu-Phe-Lys-Ala-NH2 (Disulfide bridge: Cys1-Cys5, Cys14-Cys51); Maxadilan (Lutzomyialongipalpis); L-cysteinyl-L-alpha-aspartyl-L-alanyl-L-threonyl-L-cysteinyl-L-glutaminyl-L-phenylalanyl-L-arginyl-L-lysyl-L-alanyl-L-isoleucyl-L-alpha-aspartyl-L-alpha-aspartyl-L-cysteinyl-L-glutaminyl-L-lysyl-L-glutaminyl-L-alanyl-L-histidyl-L-histidyl-L-seryl-L-asparagyl-L-valyl-L-leucyl-L-glutaminyl-L-threonyl-L-seryl-L-valyl-L-glutaminyl-L-threonyl-L-threonyl-L-alanyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-methionyl-L-alpha-aspartyl-L-threonyl-L-seryl-L-glutaminyl-L-leucyl-L-prolyl-glycyl-L-asparagyl-L-seryl-L-valyl-L-phenylalanyl-L-lysyl-L-alpha-glutamyl-L-cysteinyl-L-methionyl-L-lysyl-L-glutaminyl-L-lysyl-L-lysyl-L-lysyl-L-alpha-glutamyl-L-phenylalanyl-L-lysyl-L-alaninamide (1->5),(14->51)-bis(disulfide)

Appearance

White Powder

Purity

95%

Sequence

CDATCQFRKAIDDCQKQAHHSNVLQTSVQTTATFTSMDTSQLPGNSVFKECMKQKKKEFKA-NH2 (Disulfide bridge: Cys1-Cys5, Cys14-Cys51)

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C291H465N85O95S6/c1-27-141(12)223(368-232(412)143(14)319-236(416)161(66-40-48-96-292)324-245(425)169(74-56-104-314-291(310)311)332-259(439)183(111-155-60-34-29-35-61-155)346-248(428)173(79-88-207(304)392)340-276(456)202-133-475-474-130-160(300)235(415)345-190(118-216(403)404)256(436)320-144(15)233(413)370-226(149(20)384)287(467)364-202)281(461)355-192(120-218(407)408)264(444)351-191(119-217(405)406)265(445)363-201-132-477-476-131-200(275(455)342-179(94-106-472-25)252(432)329-167(72-46-54-102-298)242(422)334-171(77-86-205(302)390)246(426)327-164(69-43-51-99-295)240(420)325-163(68-42-50-98-294)239(419)326-165(70-44-52-100-296)243(423)335-177(83-92-214(399)400)249(429)347-182(110-154-58-32-28-33-59-154)258(438)330-162(67-41-49-97-293)237(417)322-146(17)290(470)471)362-251(431)178(84-93-215(401)402)336-244(424)168(73-47-55-103-299)331-260(440)184(112-156-62-36-30-37-63-156)353-280(460)222(140(10)11)367-272(452)198(128-380)358-263(443)188(116-211(308)396)323-213(398)124-315-277(457)203-75-57-105-376(203)289(469)194(109-137(4)5)356-250(430)174(80-89-208(305)393)338-269(449)196(126-378)359-286(466)229(152(23)387)374-268(448)193(121-219(409)410)350-253(433)180(95-107-473-26)341-270(450)197(127-379)360-285(465)228(151(22)386)373-266(446)185(113-157-64-38-31-39-65-157)354-283(463)225(148(19)383)369-234(414)145(16)321-282(462)224(147(18)382)375-288(468)230(153(24)388)372-255(435)176(82-91-210(307)395)343-278(458)220(138(6)7)366-273(453)199(129-381)361-284(464)227(150(21)385)371-254(434)175(81-90-209(306)394)337-257(437)181(108-136(2)3)352-279(459)221(139(8)9)365-267(447)189(117-212(309)397)349-271(451)195(125-377)357-262(442)187(115-159-123-313-135-317-159)348-261(441)186(114-158-122-312-134-316-158)344-231(411)142(13)318-238(418)170(76-85-204(301)389)333-241(421)166(71-45-53-101-297)328-247(427)172(339-274(201)454)78-87-206(303)391/h28-39,58-65,122-123,134-153,160-203,220-230,377-388H,27,40-57,66-121,124-133,292-300H2,1-26H3,(H2,301,389)(H2,302,390)(H2,303,391)(H2,304,392)(H2,305,393)(H2,306,394)(H2,307,395)(H2,308,396)(H2,309,397)(H,312,316)(H,313,317)(H,315,457)(H,318,418)(H,319,416)(H,320,436)(H,321,462)(H,322,417)(H,323,398)(H,324,425)(H,325,420)(H,326,419)(H,327,426)(H,328,427)(H,329,432)(H,330,438)(H,331,440)(H,332,439)(H,333,421)(H,334,422)(H,335,423)(H,336,424)(H,337,437)(H,338,449)(H,339,454)(H,340,456)(H,341,450)(H,342,455)(H,343,458)(H,344,411)(H,345,415)(H,346,428)(H,347,429)(H,348,441)(H,349,451)(H,350,433)(H,351,444)(H,352,459)(H,353,460)(H,354,463)(H,355,461)(H,356,430)(H,357,442)(H,358,443)(H,359,466)(H,360,465)(H,361,464)(H,362,431)(H,363,445)(H,364,467)(H,365,447)(H,366,453)(H,367,452)(H,368,412)(H,369,414)(H,370,413)(H,371,434)(H,372,435)(H,373,446)(H,374,448)(H,375,468)(H,399,400)(H,401,402)(H,403,404)(H,405,406)(H,407,408)(H,409,410)(H,470,471)(H4,310,311,314)/t141-,142-,143-,144-,145-,146-,147+,148+,149+,150+,151+,152+,153+,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-,190-,191-,192-,193-,194-,195-,196-,197-,198-,199-,200-,201-,202-,203-,220-,221-,222-,223-,224-,225-,226-,227-,228-,229-,230-/m0/s1

InChI Key

HCXLBYNBTBNDQZ-KFHPIRAKSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CC(=O)O)C(=O)NC(CC(=O)O)C(=O)NC1CSSCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C2CCCN2C(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCC(=O)N)CCCCN)CCC(=O)N)C)CC3=CN=CN3)CC4=CN=CN4)CO)CC(=O)N)C(C)C)CC(C)C)CCC(=O)N)C(C)O)CO)C(C)C)CCC(=O)N)C(C)O)C(C)O)C)C(C)O)CC5=CC=CC=C5)C(C)O)CO)CCSC)CC(=O)O)C(C)O)CO)CCC(=O)N)CC(C)C)CC(=O)N)CO)C(C)C)CC6=CC=CC=C6)CCCCN)CCC(=O)O)C(=O)NC(CCSC)C(=O)NC(CCCCN)C(=O)NC(CCC(=O)N)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCC(=O)O)C(=O)NC(CC7=CC=CC=C7)C(=O)NC(CCCCN)C(=O)NC(C)C(=O)O)NC(=O)C(C)NC(=O)C(CCCCN)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC8=CC=CC=C8)NC(=O)C(CCC(=O)N)NC(=O)C9CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N9)C(C)O)C)CC(=O)O)N

1. Maxadilan, the PAC1 receptor, and leishmaniasis

Yhong Li, Ethan A Lerner, Vemuri B Reddy J Mol Neurosci . 2008 Nov;36(1-3):241-4. doi: 10.1007/s12031-008-9079-1.

Maxadilan is a vasodilator peptide isolated from sand fly salivary glands. The vasodilator effects of maxadilan are mediated by the PAC1 receptor, although maxadilan and PACAP do not share sequence homology. Sand flies are the vector of the parasitic disease leishmaniasis. The peptide aids the sand fly in obtaining a blood meal while enhancing the infectivity of leishmania parasites transmitted by this arthropod vector. Aspects of maxadilan, PAC1, and leishmaniasis are discussed.

2. Maxadilan, a PAC1 receptor agonist from sand flies

Ethan A Lerner, Aurel O Iuga, Vemuri B Reddy Peptides . 2007 Sep;28(9):1651-4. doi: 10.1016/j.peptides.2007.06.021.

In 1991, a potent 61 amino acid vasodilator peptide, named maxadilan, was isolated from the salivary glands of the sand fly. Subsequently, it was shown that this peptide specifically and potently activated the mammalian PAC1 receptor, one of the three receptors for PACAP. These studies and the link between maxadilan and leishmaniasis are discussed.

3. Vasodilatory properties of recombinant maxadilan

J F Keaney Jr, M Tajima, R M Weisbrod, J Loscalzo, T S Jackson, E Lerner Am J Physiol . 1996 Sep;271(3 Pt 2):H924-30. doi: 10.1152/ajpheart.1996.271.3.H924.

Maxadilan is a peptide from the salivary gland of the sand fly Lutzomyia longipalpis, a vector for leishmaniasis. Cutaneous injection of femtomolar quantities of maxadilan produces long-lasting erythema, making it the most potent vasodilator known. Isolated rabbit thoracic and abdominal aorta, carotid artery, and iliac artery demonstrated dose-dependent arterial relaxation in response to maxadilan with a mean effective concentration (EC50) of 2.7 +/- 1.5, 2.1 +/- 0.5, 2.6 +/- 0.4, and 1.9 +/- 0.5 nM, respectively. Maxadilan proved to be at least sevenfold more potent than nitroglycerin in each arterial bed (EC50 = 25 +/- 12, 32 +/- 9, 37 +/- 10, and 22 +/- 13 nM, respectively; P < 0.05 for each vs. maxadilan). Arterial relaxation to maxadilan was independent of endothelium and was equipotent in the thoracic and abdominal aorta, carotid artery, and iliac artery. Arterial relaxation to maxadilan was not inhibited by K(+)-channel antagonists, methylene blue, quinacrine, or ouabain. Maxadilan-mediated arterial relaxation was found to be adenosine 3',5'-cyclic monophosphate (cAMP) dependent, as it was potentiated by the phosphodiesterase inhibitors 3-isobutyl-1-methylxanthine and theophylline, and it was inhibited by the protein kinase A inhibitor H-89. Consistent with this observation, incubation of thoracic aorta with maxadilan (0.1 microM) produced a time-dependent increase in arterial cAMP content coincident with arterial relaxation. Using rabbit aortic smooth muscle cells, we also observed a time-dependent reduction in intracellular calcium in response to maxadilan. Thus these data indicate that maxadilan, a peptide from the sand fly salivary gland, is a potent vasodilator that reduces intracellular calcium through a cAMP-dependent mechanism.