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Sauvagine

Catalog Number: EVT-242117

CAS Number: 74434-59-6

Molecular Formula: C202H346N56O63S

Molecular Weight: 4599 g/mol

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Product Introduction

Description

Sauvagine is a fascinating peptide with a wide array of biological effects. Isolated from the skin of the South American frog Phyllomedusa sauvagei, sauvagine is a linear peptide composed of forty amino acid residues5 6. It has been the subject of various studies due to its pharmacological actions on diuresis, the cardiovascular system, and endocrine glands5 6. The peptide has been shown to have a significant impact on gastrointestinal motility, prolactin inhibition, and hormone secretion, among other physiological processes1 2 7.

Mechanism of Action

The mechanism of action of sauvagine is multifaceted, affecting different systems in the body. In the gastrointestinal tract, sauvagine has been shown to slow gastric emptying in rats, an effect that is dose-related and lasts for several hours after administration1. This suggests a physiological role for the peptide in the mediation of gastrointestinal motility.

In the endocrine system, sauvagine has been found to inhibit prolactin secretion both in vivo and in vitro, indicating that it acts at the pituitary level2. This inhibition of prolactin is significant and dose-related, suggesting that sauvagine or a related peptide may play a crucial role in the control of prolactin secretion in mammals.

Sauvagine also influences the secretion of hormones such as ACTH, beta-endorphin, and corticosterone in rats, with its effects being dose-dependent7. The peptide's ability to induce hormone release is indicative of its role in stress and adaptive responses.

Furthermore, sauvagine has been shown to regulate Ca2+ oscillations and electrical membrane activity in melanotrope cells of Xenopus laevis, which in turn modulates the secretion of the hormone alpha-melanophore-stimulating hormone (α-MSH)3. This regulation is achieved through the modulation of Ca2+ signalling and K+ currents, altering the pattern of Ca2+ oscillations and the shape of individual action currents.

Applications in Various Fields

Gastrointestinal Research

Sauvagine's impact on gastric emptying makes it a peptide of interest in gastrointestinal research. The ability to modulate gastrointestinal motility could have implications for the treatment of disorders such as gastroparesis or functional dyspepsia1.

Endocrinology

In the field of endocrinology, sauvagine's potent prolactin-inhibiting activity opens up potential applications in conditions where prolactin regulation is necessary, such as hyperprolactinemia2. Its effects on ACTH and corticosterone secretion also make it relevant for studies on the hypothalamic-pituitary-adrenal (HPA) axis and stress response7.

Cardiovascular Studies

Sauvagine's cardiovascular effects, such as hypotension and mesenteric vasodilation, are significant for cardiovascular research. The peptide's ability to modulate blood pressure and mesenteric blood flow without the involvement of adrenergic or muscarinic receptors suggests potential therapeutic applications for cardiovascular diseases8 9.

Neuroendocrinology

The modulation of Ca2+ oscillations and electrical membrane activity by sauvagine in neuroendocrine cells highlights its importance in neuroendocrinology3. Understanding how neurotransmitters like sauvagine influence hormone secretion can lead to insights into the regulation of neuroendocrine functions.

Properties

CAS Number

74434-59-6

Product Name

Sauvagine

IUPAC Name

(4S)-5-[[(2S)-6-amino-1-[[(2S)-5-amino-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S,3S)-1-amino-3-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-5-carbamimidamido-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-carboxy-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-3-carboxy-2-[[(2S,3S)-2-[[(2S)-3-hydroxy-2-[[(2S,3S)-3-methyl-2-[[(2S)-1-[(2S)-1-[2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]acetyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]pentanoyl]amino]propanoyl]amino]-3-methylpentanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]butanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]pentanoyl]amino]hexanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-methylpentanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]amino]-4-carboxybutanoyl]amino]hexanoyl]amino]-5-oxopentanoyl]amino]-4-carboxybutanoyl]amino]hexanoyl]amino]-5-oxopentanoic acid

Molecular Formula

C202H346N56O63S

Molecular Weight

4599 g/mol

InChI

InChI=1S/C202H346N56O63S/c1-29-103(20)156(162(212)283)251-199(320)161(110(27)261)256-191(312)137(92-155(281)282)247-186(307)132(87-101(16)17)243-185(306)131(86-100(14)15)242-183(304)129(84-98(10)11)239-172(293)116(51-43-78-218-202(215)216)228-188(309)135(90-146(211)266)246-189(310)134(89-145(210)265)238-164(285)109(26)220-163(284)108(25)221-166(287)118(54-63-142(207)262)229-173(294)119(55-64-143(208)263)230-167(288)111(46-34-38-73-203)224-175(296)121(58-67-149(269)270)232-169(290)113(48-36-40-75-205)225-176(297)122(59-68-150(271)272)233-174(295)120(56-65-144(209)264)231-168(289)112(47-35-39-74-204)226-177(298)124(61-70-152(275)276)236-195(316)157(104(21)30-2)252-179(300)125(62-71-153(277)278)237-196(317)158(105(22)31-3)253-180(301)126(72-81-322-28)235-170(291)114(49-37-41-76-206)223-171(292)115(50-42-77-217-201(213)214)227-181(302)127(82-96(6)7)241-184(305)130(85-99(12)13)240-178(299)123(60-69-151(273)274)234-182(303)128(83-97(8)9)245-192(313)138(94-259)249-187(308)133(88-102(18)19)244-190(311)136(91-154(279)280)248-197(318)159(106(23)32-4)254-193(314)139(95-260)250-198(319)160(107(24)33-5)255-194(315)140-52-44-80-258(140)200(321)141-53-45-79-257(141)148(268)93-219-165(286)117-57-66-147(267)222-117/h96-141,156-161,259-261H,29-95,203-206H2,1-28H3,(H2,207,262)(H2,208,263)(H2,209,264)(H2,210,265)(H2,211,266)(H2,212,283)(H,219,286)(H,220,284)(H,221,287)(H,222,267)(H,223,292)(H,224,296)(H,225,297)(H,226,298)(H,227,302)(H,228,309)(H,229,294)(H,230,288)(H,231,289)(H,232,290)(H,233,295)(H,234,303)(H,235,291)(H,236,316)(H,237,317)(H,238,285)(H,239,293)(H,240,299)(H,241,305)(H,242,304)(H,243,306)(H,244,311)(H,245,313)(H,246,310)(H,247,307)(H,248,318)(H,249,308)(H,250,319)(H,251,320)(H,252,300)(H,253,301)(H,254,314)(H,255,315)(H,256,312)(H,269,270)(H,271,272)(H,273,274)(H,275,276)(H,277,278)(H,279,280)(H,281,282)(H4,213,214,217)(H4,215,216,218)/t103-,104-,105-,106-,107-,108-,109-,110+,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,156-,157-,158-,159-,160-,161-/m0/s1

InChI Key

ILCVKEBXPLEGOY-ZLFMSJRASA-N

SMILES

CCC(C)C(C(=O)N)NC(=O)C(C(C)O)NC(=O)C(CC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(=O)N)NC(=O)C(CC(=O)N)NC(=O)C(C)NC(=O)C(C)NC(=O)C(CCC(=O)N)NC(=O)C(CCC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CCC(=O)O)NC(=O)C(CCCCN)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C(CCCCN)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)CC)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)CC)NC(=O)C(CCSC)NC(=O)C(CCCCN)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)C(CC(=O)O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)CC)NC(=O)C1CCCN1C(=O)C2CCCN2C(=O)CNC(=O)C3CCC(=O)N3

Synonyms

(D-Phe(11),His(12),Nle(17))Svg(11-40)
0-Tyr-sauvagine
11-D-Phe-12-His-17-Nle-Svg(11-40)
aSvg-30, Nle(17)-
C-terminal sauvagine(17-40)
K 41498
K-41498
K41498
sauvagine
sauvagine (11-40), D-Phe(11)-His(12)-Nle(17)-
sauvagine (11-40), D-phenylalanyl(11)-histidyl(12)-norleucyl(17)-
sauvagine(17-40)
sauvagine, Tyr(0)-
sauvagine, tyrosyl(0)-

Canonical SMILES

Isomeric SMILES

CC[C@H](C)[C@@H](C(=O)N)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]2CCCN2C(=O)CNC(=O)[C@@H]3CCC(=O)N3

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