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Metastin (human)

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Metastin (human) is an endogenous ligand to G-protein-coupled orphan receptors such as OT7T175 (also known as AXOR12) and GPR54. Kisspeptin-54 was initially termed as "metastin" because of its capacity to inhibit tumor metastasis. This peptide has been considered as the major product of the human KISS1 gene. It binds with high affinity to rat and human KISS1 receptors with Ki values of 1.80 and 1.45 nM respectively.

Category

Peptide Inhibitors

Catalog number

BAT-015366

CAS number

374683-24-6

Molecular Formula

C258H401N79O78

Molecular Weight

5857.49

Specification
Reference Reading

IUPAC Name

(4S)-4-[[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[(2-aminoacetyl)amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]-5-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-5-amino-1-[(2S)-2-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S,3S)-1-[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-5-amino-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-1,5-dioxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]carbamoyl]pyrrolidin-1-yl]-1,5-dioxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

Synonyms

Metastin (human); H-Gly-Thr-Ser-Leu-Ser-Pro-Pro-Pro-Glu-Ser-Ser-Gly-Ser-Arg-Gln-Gln-Pro-Gly-Leu-Ser-Ala-Pro-His-Ser-Arg-Gln-Ile-Pro-Ala-Pro-Gln-Gly-Ala-Val-Leu-Val-Gln-Arg-Glu-Lys-Asp-Leu-Pro-Asn-Tyr-Asn-Trp-Asn-Ser-Phe-Gly-Leu-Arg-Phe-NH2; glycyl-L-threonyl-L-seryl-L-leucyl-L-seryl-L-prolyl-L-prolyl-L-prolyl-L-alpha-glutamyl-L-seryl-L-seryl-glycyl-L-seryl-L-arginyl-L-glutaminyl-L-glutaminyl-L-prolyl-glycyl-L-leucyl-L-seryl-L-alanyl-L-prolyl-L-histidyl-L-seryl-L-arginyl-L-glutaminyl-L-isoleucyl-L-prolyl-L-alanyl-L-prolyl-L-glutaminyl-glycyl-L-alanyl-L-valyl-L-leucyl-L-valyl-L-glutaminyl-L-arginyl-L-alpha-glutamyl-L-lysyl-L-alpha-aspartyl-L-leucyl-L-prolyl-L-asparagyl-L-tyrosyl-L-asparagyl-L-tryptophyl-L-asparagyl-L-seryl-L-phenylalanyl-glycyl-L-leucyl-L-arginyl-L-phenylalaninamide; KP-54

Appearance

White or off-white lyophilized powder

Purity

≥95%

Sequence

GTSLSPPPESSGSRQQPGLSAPHSRQIPAPQGAVLVQREKDLPNYNWNSFGLRF
(Modifications: Phe-54 = C-terminal amide)

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C258H401N79O78/c1-21-131(16)204(329-220(381)152(70-77-189(264)351)301-213(374)147(53-34-84-281-257(274)275)299-234(395)173(118-341)322-226(387)164(103-140-110-278-123-288-140)315-242(403)181-58-38-87-331(181)247(408)133(18)290-232(393)172(117-340)321-222(383)158(95-125(4)5)293-197(359)114-287-238(399)178-55-36-88-332(178)249(410)155(71-78-190(265)352)306-218(379)150(68-75-187(262)349)300-212(373)146(52-33-83-280-256(272)273)298-233(394)171(116-339)294-198(360)113-286-210(371)170(115-338)319-237(398)175(120-343)320-219(380)154(73-80-200(363)364)304-241(402)183-60-40-90-334(183)252(413)185-62-43-93-337(185)253(414)184-61-42-92-336(184)251(412)177(122-345)325-223(384)159(96-126(6)7)308-236(397)176(121-344)324-246(407)205(135(20)346)326-194(356)108-260)254(415)335-91-41-56-179(335)239(400)291-134(19)248(409)330-86-37-57-180(330)240(401)303-149(67-74-186(261)348)208(369)284-111-195(357)289-132(17)207(368)327-202(129(12)13)245(406)317-160(97-127(8)9)231(392)328-203(130(14)15)244(405)305-151(69-76-188(263)350)216(377)296-145(51-32-82-279-255(270)271)211(372)302-153(72-79-199(361)362)217(378)295-144(50-30-31-81-259)215(376)314-168(107-201(365)366)230(391)318-169(98-128(10)11)250(411)333-89-39-59-182(333)243(404)316-167(106-193(268)355)228(389)310-162(101-138-63-65-141(347)66-64-138)224(385)312-165(104-191(266)353)227(388)311-163(102-139-109-283-143-49-29-28-48-142(139)143)225(386)313-166(105-192(267)354)229(390)323-174(119-342)235(396)309-161(100-137-46-26-23-27-47-137)209(370)285-112-196(358)292-157(94-124(2)3)221(382)297-148(54-35-85-282-258(276)277)214(375)307-156(206(269)367)99-136-44-24-22-25-45-136/h22-29,44-49,63-66,109-110,123-135,144-185,202-205,283,338-347H,21,30-43,50-62,67-108,111-122,259-260H2,1-20H3,(H2,261,348)(H2,262,349)(H2,263,350)(H2,264,351)(H2,265,352)(H2,266,353)(H2,267,354)(H2,268,355)(H2,269,367)(H,278,288)(H,284,369)(H,285,370)(H,286,371)(H,287,399)(H,289,357)(H,290,393)(H,291,400)(H,292,358)(H,293,359)(H,294,360)(H,295,378)(H,296,377)(H,297,382)(H,298,394)(H,299,395)(H,300,373)(H,301,374)(H,302,372)(H,303,401)(H,304,402)(H,305,405)(H,306,379)(H,307,375)(H,308,397)(H,309,396)(H,310,389)(H,311,388)(H,312,385)(H,313,386)(H,314,376)(H,315,403)(H,316,404)(H,317,406)(H,318,391)(H,319,398)(H,320,380)(H,321,383)(H,322,387)(H,323,390)(H,324,407)(H,325,384)(H,326,356)(H,327,368)(H,328,392)(H,329,381)(H,361,362)(H,363,364)(H,365,366)(H4,270,271,279)(H4,272,273,280)(H4,274,275,281)(H4,276,277,282)

InChI Key

KAHDONZOCXSKII-NJVVDGNHSA-N

Canonical SMILES

CCC(C)C(C(=O)N1CCCC1C(=O)NC(C)C(=O)N2CCCC2C(=O)NC(CCC(=O)N)C(=O)NCC(=O)NC(C)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(CCC(=O)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCC(=O)O)C(=O)NC(CCCCN)C(=O)NC(CC(=O)O)C(=O)NC(CC(C)C)C(=O)N3CCCC3C(=O)NC(CC(=O)N)C(=O)NC(CC4=CC=C(C=C4)O)C(=O)NC(CC(=O)N)C(=O)NC(CC5=CNC6=CC=CC=C65)C(=O)NC(CC(=O)N)C(=O)NC(CO)C(=O)NC(CC7=CC=CC=C7)C(=O)NCC(=O)NC(CC(C)C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC8=CC=CC=C8)C(=O)N)NC(=O)C(CCC(=O)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CO)NC(=O)C(CC9=CNC=N9)NC(=O)C1CCCN1C(=O)C(C)NC(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C1CCCN1C(=O)C(CCC(=O)N)NC(=O)C(CCC(=O)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(CO)NC(=O)CNC(=O)C(CO)NC(=O)C(CO)NC(=O)C(CCC(=O)O)NC(=O)C1CCCN1C(=O)C1CCCN1C(=O)C1CCCN1C(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)CN

1. Metabolic regulation of kisspeptin - the link between energy balance and reproduction

Víctor M Navarro Nat Rev Endocrinol . 2020 Aug;16(8):407-420. doi: 10.1038/s41574-020-0363-7.

Hypothalamic kisspeptin neurons serve as the nodal regulatory centre of reproductive function. These neurons are subjected to a plethora of regulatory factors that ultimately affect the release of kisspeptin, which modulates gonadotropin-releasing hormone (GnRH) release from GnRH neurons to control the reproductive axis. The presence of sufficient energy reserves is critical to achieve successful reproduction. Consequently, metabolic factors impose a very tight control over kisspeptin synthesis and release. This Review offers a synoptic overview of the different steps in which kisspeptin neurons are subjected to metabolic regulation, from early developmental stages to adulthood. We cover an ample array of known mechanisms that underlie the metabolic regulation of KISS1 expression and kisspeptin release. Furthermore, the novel role of kisspeptin neurons as active players within the neuronal circuits that govern energy balance is discussed, offering evidence of a bidirectional role of these neurons as a nexus between metabolism and reproduction.

2. Pubertal development and regulation

Ana Paula Abreu, Ursula B Kaiser Lancet Diabetes Endocrinol . 2016 Mar;4(3):254-264. doi: 10.1016/S2213-8587(15)00418-0.

Puberty marks the end of childhood and is a period when individuals undergo physiological and psychological changes to achieve sexual maturation and fertility. The hypothalamic-pituitary-gonadal axis controls puberty and reproduction and is tightly regulated by a complex network of excitatory and inhibitory factors. This axis is active in the embryonic and early postnatal stages of life and is subsequently restrained during childhood, and its reactivation culminates in puberty initiation. The mechanisms underlying this reactivation are not completely known. The age of puberty onset varies between individuals and the timing of puberty initiation is associated with several health outcomes in adult life. In this Series paper, we discuss pubertal markers, epidemiological trends of puberty initiation over time, and the mechanisms whereby genetic, metabolic, and other factors control secretion of gonadotropin-releasing hormone to determine initiation of puberty.

3. Dramatic elevation of plasma metastin concentrations in human pregnancy: metastin as a novel placenta-derived hormone in humans

Chieko Kitada, Yoshihiro Takatsu, Tetsuya Ohtaki, Masahiko Fujino, Hirokazu Matsumoto, Satoshi Usuki, Yasuko Horikoshi J Clin Endocrinol Metab . 2003 Feb;88(2):914-9. doi: 10.1210/jc.2002-021235.

Metastin is a novel peptide that was recently isolated from human placenta as the endogenous ligand of an orphan heptahelical receptor, hOT7T175. Metastin has been shown to suppress the motility of hOT7T175-transfected melanoma cells; however, studies of the physiological function of metastin have begun only recently. To investigate the possibility that metastin is an endocrine peptide, we determined the immunoreactive (ir-) metastin concentration in human plasma using our newly developed, sensitive, and specific two-site enzyme immunoassay. The plasma concentrations of ir-metastin in males and females were 1.30 +/- 0.14 (n = 12) and 1.31 +/- 0.37 fmol/ml (n = 10), respectively. As metastin is known to be abundant in human placenta, the ir-metastin concentration in the maternal plasma was then determined. The ir-metastin concentrations were 1230 +/- 346 fmol/ml (n = 11) in the first trimester, 4590 +/- 555 (n = 16) in the second trimester, and 9590 +/- 1640 (n = 12) in the third trimester. On d 5 after delivery, the ir-metastin concentration returned to nearly the nonpregnant level (7.63 +/- 1.33 fmol/ml; n = 10), suggesting that ir-metastin increases in pregnancy and is derived mainly from the placenta. The plasma from both nonpregnant and pregnant women showed a single ir-metastin peak at the same retention time as authentic metastin on reverse phase HPLC analysis, indicating that the major portion of the circulating metastin, as determined by our two-site enzyme immunoassay, represents endogenous metastin. Histochemical studies of human placenta localized metastin mRNA and immunoreactivity to the syncytiotrophoblasts. The present study provides evidence for metastin as a novel placenta-derived hormone in humans.