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M2816

Sigma-Aldrich

Metastin (45-54) amide, human

≥95%

Synonym(s):

Gene product (112-121) amide, human, KiSS-1, Kisspeptin-10

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About This Item

Empirical Formula (Hill Notation):
C63H83N17O14
Molecular Weight:
1302.44
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.32

Quality Level

Assay

≥95%

UniProt accession no.

storage temp.

−20°C

SMILES string

CC(C)C[C@H](NC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](N)Cc4ccc(O)cc4)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc5ccccc5)C(N)=O

InChI

1S/C63H83N17O14/c1-34(2)24-45(58(90)74-43(18-11-23-70-63(68)69)57(89)75-44(54(67)86)26-35-12-5-3-6-13-35)73-53(85)32-72-56(88)46(27-36-14-7-4-8-15-36)77-62(94)50(33-81)80-61(93)49(30-52(66)84)79-59(91)47(28-38-31-71-42-17-10-9-16-40(38)42)78-60(92)48(29-51(65)83)76-55(87)41(64)25-37-19-21-39(82)22-20-37/h3-10,12-17,19-22,31,34,41,43-50,71,81-82H,11,18,23-30,32-33,64H2,1-2H3,(H2,65,83)(H2,66,84)(H2,67,86)(H,72,88)(H,73,85)(H,74,90)(H,75,89)(H,76,87)(H,77,94)(H,78,92)(H,79,91)(H,80,93)(H4,68,69,70)/t41-,43-,44-,45-,46-,47-,48-,49-,50-/m0/s1

InChI key

RITKWYDZSSQNJI-INXYWQKQSA-N

Gene Information

human ... KISS1(3814)

Amino Acid Sequence

Tyr-Asn-Trp-Asn-Ser-Phe-Gly-Leu-Arg-Phe-NH2

General description

Metastin is also known as kisspeptin 1 (KISS1). It is encoded by KISS1 gene, that is mapped to human chromosome 1q32. Metastin is a tumor suppressor protein, made up of 145 amino acids. The protein fragments contain RFamide motif at the C- terminal end. The encoded protein is expressed in the human hypothalamus, gonads, placenta, liver and pancreas. This novel peptide is mainly isolated from the human placenta.

Application

Metastin (45-54) amide has been used in progesterone release experiments from MA-10 cells. It has also been used to induce gonadal differentiation in clownfish.

Biochem/physiol Actions

Metastin functions as a tumor suppressor via inhibiting secondary tumor growth. Activation of KISS1R (KISS1 receptor), upon binding KISS1, enhances intracellular calcium and activates MAPKs, which restricts cell motility and proliferation. Metastin acts as a potential therapeutic target for various cancers including melanoma, thyroid cancer and bladder cancer, squamous cell carcinoma of the esophagus gastric cancer, hepatocellular carcinoma and breast cancer. Metastin has a crucial role in reproduction. It regulates hypothalamic-pituitary-gonadal axis role via controlling gonadotropin-releasing hormone (GnRH) secretion and determines the onset of puberty. Mutation of the gene leads to central precocious puberty (CPP) in male and dysfunction of metastin signaling causes isolated hypogonadotropic hypogonadism (IHH) in humans and mice. Metastin has the ability to enhance the plasma levels of gonadotropins (follicle-stimulating hormone and luteinizing hormone) and stimulate ovulation in prepubertal female rats.
Metastin is an endogenous ligand to G-protein-coupled orphan receptors such as OT7T175 (also known as AXOR12) and GPR54. Novel placenta-derived hormone. The amide form of metastin is found to be 3-10 times more active than the free acid form of metastin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Does kisspeptin signaling have a role in the testes?
Hua M, et al.
Frontiers in Endocrinology, 4, 198-198 (2013)
Lan Yu et al.
Diagnostic pathology, 12(1), 23-23 (2017-03-04)
Recurrence and metastasis are the usual manifestations of treatment failure of epithelial ovarian carcinoma (EOC). Vasculogenic mimicry (VM; blood supply development often seen in highly aggressive cancers), aldehyde dehydrogenase 1 (ALDH1, cancer stem cell biomarker), KiSS-1 (suppressor of tumor metastasis)
Effects of gonadotropin inhibitory hormone or gonadotropin-releasing hormone on reproduction-related genes in the protandrous cinnamon clownfish, Amphiprion melanopus
Choi Y J, et al.
General and Comparative Endocrinology, 235, 89-99 (2016)
Peripheral administration of metastin induces marked gonadotropin release and ovulation in the rat
Matsui H, et al.
Biochemical and Biophysical Research Communications, 320(2), 383-388 (2004)
Wui-Jung Shin et al.
APMIS : acta pathologica, microbiologica, et immunologica Scandinavica, 124(4), 291-298 (2016-01-27)
Downregulated expression of KiSS-1 has been correlated with tumor progression, metastasis, and patient prognosis in various human malignancies. However, there is no information regarding the expression of KiSS-1 in oral squamous cell carcinoma (OSCC). Our aims were to examine KiSS-1

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