Lysipressin is a pressor peptide isolated from marsupials and pigs that binds to VP receptors, which are analogous to human Vasopressin 2 (V2) receptors. Lysipressin induces contractions in smooth muscle and potentiates effects of gastric lesioning in animal models.
CAT No: 10-101-23
CAS No:50-57-7
Synonyms/Alias:LYPRESSIN;Lysipressin;Lysine vasopressin;50-57-7;Syntopressin;8-L-Lysinevasopressin;Postacton;Diapid;Lysine pitressin;Lipresina;Lypressine;Vasopressin, 8-L-lysine-;Vasopressin pig;L-Lysine vasopressin;Vasopressin-8-lysine;Vasopressin, 8-L-lysine;[Lys8]-Vasopressin;DTXSID8048575;(8-Lysine)vasopressin;Vasopressin (lysine form);8-L-Lysine vasopressin;50-57-7 (free base);7CZF3L922Y;DTXCID8028501;(Lys8)-Vasopressin;L-Cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-lysylglycinamide cyclic (1->6)-disulfide;[8-Lysine]vasopressin;Lysine-vasopressin;(2S)-N-[(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide;LVP;Lipressina;Lypressinum;Lysopressin;Lysylvasopressin;Lys Vasopressin;Lysyl Vasopressin;CAS-50-57-7;Vasopressin, Lysyl;(S)-N-((S)-6-amino-1-((2-amino-2-oxoethyl)amino)-1-oxohexan-2-yl)-1-((4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl)pyrrolidine-2-carboxamide;L-8;Vasopressin, Lysine;Lipressina [DCIT];8 Lysine Vasopressin;8-Lysine Vasopressin;Vasopressin, 8-Lysine;Lipresina [INN-Spanish];Lypressine [INN-French];Lypressinum [INN-Latin];UNII-7CZF3L922Y;Lysipressin?;3-(Phenylalanine)-8-lysine oxytocin;L-lysinamide,;Lysine-ADH;Lypressin [USAN:USP:INN:BAN];NCGC00181743-01;NCGC00181743-02;EINECS 200-050-5;MFCD00076754;BRN 4648365;[Lys8]AVP;LYPRESSIN (MART.);LYPRESSIN (USP-RS);SCHEMBL33287;GTPL2172;CHEMBL1200690;LYPRESSIN (USP IMPURITY);CHEBI:94802;H01BA03;Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH2, cyclic 1-6 disulfide;HY-P0004;Tox21_112902;Tox21_113427;AKOS030529559;CCG-270620;CS-5838;DB14642;FL38924;NS00032082;Oxytocin, 3-(L-phenylalanine)-8-L-lysine-;Vasopressin, 8-L-lysine- (7CI,8CI,9CI);C75370;l]carbonyl]-L-prolyl-N-(2-amino-2-oxoethyl)-;BRD-K93331255-001-01-2;BRD-K93331255-001-02-0;Q27082434;1,2-Dithia-5,8,11,14,17-pentaazacycloeicosane-10-propionamide;Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH2[Disulfide Bridge: 1-6];(2S)-N-[(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(phenylmethyl)1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide;(2S)-N-[(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(phenylmethyl)-1,2-dithia-5,8,11,14,17-pentazacycloeicos-4-yl]-oxomethyl]-2-pyrrolidinecarboxamide;1-[[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(phenylmethyl)-1,2-dithia-5,8,11,14,17-pentaazacycloeicos-4-y;19-amino-4-[2-[[5-amino-1-[(carbamoylmethyl)carbamoyl]pentyl]carbamoyl]-1-pyrrolidinylcarbonyl]-13-benzyl-7-(carbamoylmethyl)-16-p-hydroxybenzyl-6,9,12,15,18-pentaoxo- (6CI);200-050-5;Glycinamide, L-cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-lysyl-, cyclic (1>6)-disulfide;L 8;L-CYSTEINYL-L-TYROSYL-L-PHENYLALANYL-L-GLUTAMINYL-L-ASPARAGINYL-L-CYSTEINYL-L-PROLYL-L-LYSYLGLYCINAMIDE CYCLIC (1->6)-DISULPHIDE;L-Cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-lysylglycinamide cyclic (1-6)-disulfide;
Lysipressin is a synthetic peptide analog of vasopressin, classified within the family of nonapeptide hormones that play a pivotal role in the regulation of water balance and vascular tone. Structurally, it is characterized by a distinct amino acid sequence that confers unique receptor selectivity, particularly toward vasopressin V1 receptors. Due to its close resemblance to endogenous vasopressin, lysipressin has garnered significant interest in the field of biochemical and physiological research. Its utility as a research tool is underpinned by its ability to selectively mimic or modulate specific vasopressin-mediated pathways, making it a valuable compound for dissecting the molecular mechanisms underlying vascular and renal function.
Receptor Pharmacology: Lysipressin is frequently employed in receptor binding studies to elucidate the selectivity and affinity profiles of vasopressin analogs at V1-type receptors. By serving as a reference ligand, it enables researchers to differentiate between V1 and V2 receptor-mediated responses, facilitating the characterization of receptor subtypes in various tissues. This application is instrumental in advancing the understanding of vasopressin receptor pharmacology and supports the development of novel receptor modulators.
Signal Transduction Research: The compound is widely used to investigate intracellular signaling cascades activated by vasopressin receptor engagement. In particular, lysipressin's ability to stimulate phospholipase C and induce inositol phosphate turnover provides a robust model for studying calcium mobilization and protein kinase C activation in smooth muscle and other responsive cell types. These studies are critical for unraveling the downstream effects of vasopressinergic signaling and for mapping the molecular events that govern vasoconstriction and cellular contractility.
Vascular Physiology Studies: Lysipressin serves as a functional probe in experimental models of vascular tone regulation. Its potent vasoconstrictive properties make it an ideal tool for assessing the responsiveness of isolated blood vessels or perfused organ systems to peptide-mediated constriction. Researchers utilize it to quantify the contractile capacity of vascular smooth muscle and to explore the interplay between vasopressin pathways and other vasoactive agents, thereby gaining insights into the mechanisms of blood pressure regulation and vascular reactivity.
Renal Function Analysis: In the context of renal physiology, lysipressin is applied to study water reabsorption and electrolyte handling in isolated kidney preparations or cell-based systems. By selectively activating vasopressin-sensitive pathways, it allows for the dissection of antidiuretic hormone action at the molecular and cellular levels. This approach is particularly valuable for investigating the regulation of aquaporin channels, sodium transport, and the hormonal control of renal concentrating ability under various experimental conditions.
Peptide Structure-Activity Relationship (SAR) Studies: The defined sequence and receptor selectivity of lysipressin make it an important reference compound in structure-activity relationship investigations. Researchers utilize it to benchmark the activity and specificity of novel vasopressin analogs or peptide mimetics. By comparing functional outcomes and receptor interactions, these studies contribute to the rational design of new peptide-based probes and enhance the understanding of the structural determinants governing vasopressin receptor engagement.
The neurohypophyseal hormones of the hippopotamus (Hippopotamus amphibius) and collared peccary (Tayassu angulatus) were isolated by molecular sieving and preparative high-pressure liquid chromatography (HPLC). Oxytocin and arginine vasopressin have been identified by their amino acid compositions and their retention times in HPLC. Lysipressin (lysine vasopressin) was not detected in posterior pituitaries of two hippopotami and nine peccaries (less than 2% of arginine vasopressin in molar ratios). Among the suborder Suiformes of Artiodactyla, the families Hippopotamidae and Tayassuidae do not seem to possess lysipressin, in contrast to the family Suidae in which the pig has lysipressin in place of arginine vasopressin.
Rouille, Y., Chauvet, M. T., Chauvet, J., Acher, R., & Hadley, M. E. (1988). The distribution of lysine vasopressin (lysipressin) in placental mammals: a reinvestigation of the Hippopotamidae (Hippopotamus amphibius) and Tayassuidae (Tayassu angulatus) families. General and comparative endocrinology, 71(3), 475-483.
4. The spatiotemporal control of signalling and trafficking of the GLP-1R
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