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SML3075

Sigma-Aldrich

MMK-1 trifluoroacetate

≥95% (HPLC)

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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
Empirical Formula (Hill Notation):
C75H123N19O18S · xC2HF3O2
CAS Number:
271246-66-3
Molecular Weight:
1610.96 (free base basis)

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Takahiro Tsuruki et al.
Peptides, 27(4), 820-825 (2005-09-27)
Oral administration for 6 days of 100 mg/kg MMK-1, an agonist peptide selective for the FPRL1 receptor, suppressed alopecia induced by the anticancer drug etoposide in neonatal rats. The anti-alopecia effect of orally administered MMK-1 was not inhibited by pyrilamine
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)
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
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
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
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