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Key Documents

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

Quality Level

100

assay

≥95% (HPLC)

form

film or powder

color

white to beige

storage temp.

−20°C

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.).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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C Klein et al.
Nature biotechnology, 16(13), 1334-1337 (1998-12-16)
We describe a procedure for isolating agonists for mammalian G protein-coupled receptors of unknown function. Human formyl peptide receptor like-1 (FPRL-1) receptor, originally identified as an orphan G protein-coupled receptor related to the formyl peptide receptor (FPR1), was expressed in
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
Regina Tavano et al.
Nanobiomedicine, 3, 2-2 (2016-01-01)
We tested whether amorphous SiO2-NPs and formylpeptide receptor (FPRs) agonists synergistically activate human monocytes and neutrophil polymorphonuclear granulocytes (PMNs). Peptide ligands specifically binding to FPR1 (f-MLP) and to FPR2 (MMK-1, WKYMVM and WKYMVm) human isoforms did not modify the association
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
FPRL1 receptor agonist peptides prevent etoposide-induced alopecia in neonatal rats.
Takahiro Tsuruki et al.
The Journal of investigative dermatology, 123(1), 242-243 (2004-06-12)
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