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Merck
CN

SML3075

Sigma-Aldrich

MMK-1 trifluoroacetate

≥95% (HPLC)

Synonym(s):

GTPL6240, L-Methionine, L-leucyl-L--glutamyl-L-seryl-L-isoleucyl-L-phenylalanyl-L-arginyl-L-seryl-L-leucyl-L-leucyl-L-phenylalanyl-L-arginyl-L-valyl-, LESIFRSLLFRVM trifluoroacetate, Leu-Glu-Ser-Ile-Phe-Arg-Ser-Leu-Leu-Phe-Arg-Val-Met trifluoroacetate, MMK-1 TFA

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About This Item

Empirical Formula (Hill Notation):
C75H123N19O18S · xC2HF3O2
CAS Number:
271246-66-3
Molecular Weight:
1610.96 (free base basis)
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Quality Level

100

Assay

≥95% (HPLC)

form

film or powder

color

white to beige

storage temp.

−20°C

SMILES string

S(CC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CC(C)C)CCC(=O)O)CO)[C@H](CC)C)Cc2ccccc2)CCCN=C(N)N)CO)CC(C)C)CC(C)C)Cc1ccccc1)CCCN=C(N)

InChI

1S/C75H123N19O18S/c1-12-44(10)60(94-70(108)57(39-96)92-63(101)50(27-28-58(97)98)83-61(99)47(76)33-40(2)3)72(110)90-55(37-46-23-17-14-18-24-46)68(106)84-48(25-19-30-81-74(77)78)62(100)91-56(38-95)69(107)88-53(35-42(6)7)65(103)87-52(34-41(4)5)66(104)89-54(36-45-21-15-13-16-22-45)67(105)85-49(26-20-31-82-75(79)80)64(102)93-59(43(8)9)71(109)86-51(73(111)112)29-32-113-11/h13-18,21-24,40-44,47-57,59-60,95-96H,12,19-20,25-39,76H2,1-11H3,(H,83,99)(H,84,106)(H,85,105)(H,86,109)(H,87,103)(H,88,107)(H,89,104)(H,90,110)(H,91,100)(H,92,101)(H,93,102)(H,94,108)(H,97,98)(H,111,112)(H4,77,78,81)(H4,79,80,82)/t44-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57-,59-,60-/m0/s1

InChI key

PWBQRCXCXXGUGY-AJOXZCOLSA-N

Biochem/physiol Actions

MMK-1 is a potent and selective FPR2 (FPRL-1) agonist (Ca2+ flux EC50 <2 nM/FPR2 vs. >10 μM/FPR1 with respective HEK293 transfectants) and an effective calcium-mobilizing and chemotactic agent for human monocytes & neutrophils (1-1000 nM). MMK-1 increases pertussis toxin-sensitive inflammatory cytokines production in human monocyte cultures (50 ng/mL PT & 10 μM MMK-1), exerts anxiolytic-like activities in mice (100 pmol/mouse icv) and shows anti-alopecia efficacy in rats in vivo (100 mg/kg p.o. or 10 mg/kg i.p.).
Potent and selective FPR2 (FPRL-1) agonist and monocytes/neutrophils chemotactic agent with anti-alopecia efficacy in vivo.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000128008
0000125702

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Hui Zhao et al.
Peptides, 83, 16-20 (2016-08-01)
Rubimetide (Met-Arg-Trp), which had been isolated as an antihypertensive peptide from an enzymatic digest of spinach ribulose-bisphosphate carboxylase/oxygenase (Rubisco), showed anxiolytic-like activity prostaglandin (PG) D2-dependent manner in the elevated plus-maze test after administration at a dose of 0.1mg/kg (ip.) or
Takahiro Tsuruki et al.
Bioscience, biotechnology, and biochemistry, 71(5), 1198-1202 (2007-05-09)
Previously, we found that an intraperitoneally administered chemotactic peptide, N-formyl-Met-Leu-Phe (fMLP), and MMK-1, a selective agonist of formyl peptide receptor-like 1 (FPRL1) receptor, the low affinity subtype of the fMLP receptor, prevented the alopecia in neonatal rats induced by the
Fu-Chao Liu et al.
Redox biology, 26, 101273-101273 (2019-07-22)
Neutrophil infiltration plays a significant pathological role in inflammatory diseases. NADPH oxidase type 2 (NOX2) is a respiratory burst oxidase that generates large amounts of superoxide anion (O2•-) and subsequent other reactive oxygen species (ROS). NOX2 is an emerging therapeutic
Sang Doo Kim et al.
Journal of immunology (Baltimore, Md. : 1950), 183(9), 5511-5517 (2009-10-22)
We determined the expression of the formyl peptide receptor (FPR) family and the functional roles of the FPR family in NK cells. All tested human NK cells express two members of the FPR family (FPR1 and FPR2). The expression of
J Y Hu et al.
Journal of leukocyte biology, 70(1), 155-161 (2001-07-04)
Human phagocytic leukocytes express the seven-transmembrane G-protein-coupled receptors formyl peptide receptor (FPR) and FPR-like 1 (FPRL1). MMK-1, a synthetic peptide derived from a random peptide library, is reported to induce calcium mobilization specifically in human FPRL1 gene-transfected cells. However, its
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