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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
Pricing and availability is not currently available.

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000128008
0000125702

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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
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
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)
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
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
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