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Merck
CN

F3506

Sigma-Aldrich

N-甲酰-甲硫氨酰-亮氨酰-苯丙氨酸

≥97% (HPLC)

别名:

N-甲酰-L-甲硫氨酰-L-亮氨酰-L-苯丙氨酸, fMLF, fMLP(用词错误,但已被广泛使用), 趋化肽

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About This Item

经验公式(希尔记法):
C21H31N3O5S
CAS号:
分子量:
437.55
Beilstein:
2315783
MDL编号:
UNSPSC代码:
12352200
PubChem化学物质编号:
NACRES:
NA.32

质量水平

检测方案

≥97% (HPLC)

形式

powder

分子量

437.55

储存条件

(Keep container tightly closed in a dry and well-ventilated place)

技术

activity assay: suitable

溶解性

acetic acid: 20 mg/mL, clear, colorless

储存温度

−20°C

SMILES字符串

CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(O)=O

InChI

1S/C21H31N3O5S/c1-14(2)11-17(23-19(26)16(22-13-25)9-10-30-3)20(27)24-18(21(28)29)12-15-7-5-4-6-8-15/h4-8,13-14,16-18H,9-12H2,1-3H3,(H,22,25)(H,23,26)(H,24,27)(H,28,29)/t16-,17-,18-/m0/s1

InChI key

PRQROPMIIGLWRP-BZSNNMDCSA-N

基因信息

human ... FPR1(2357)

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Amino Acid Sequence

NFor-Met-Leu-Phe

一般描述

N-甲酰-甲硫氨酰-亮氨酰-苯丙氨酸是(N-Formyl-Met-Leu-Phe, fMLP)一种趋化因子肽,可作用于多形核白细胞(PMN)、中性粒细胞等

研究领域:细胞信号传导

应用

N-甲酰-甲硫氨酰-亮氨酰-苯丙氨酸已用于:

  • 中性粒细胞Zigmond室法趋化分析中的梯度构建
  • 中性粒细胞趋化测定
  • 确定MAPK活化蛋白激酶-2(MAPKAPK-2)和/或p38是否参与由N-甲酰-甲硫氨酰-亮氨酰-苯丙氨酸刺激的人多形核白细胞(PMN)的信号传导途径。

生化/生理作用

N-甲酰-甲硫氨酰-亮氨酰-苯丙氨酸可诱导磷酸肌醇3-激酶γ(PI3K)γ-/- 中性粒细胞的趋化、促进F-肌动蛋白的粘附和聚合,以及Fcγ受体介导的吞噬作用和细胞内Ca2+ 的释放。它可作为炎症因子,激活多形核白细胞(PMNs),且不会产生5-羟基山梨酸(5-HETE)和白三烯B4 (LTB4)。其对中性粒细胞的影响,以及腺苷酸环化酶的抑制效果可被百日咳毒素所抑制。
有效的趋化肽。诱导巨噬细胞的代谢爆发,并伴随着呼吸速率的增加、溶酶体酶的分泌以及超氧阴离子的产生。
白细胞趋化的强效诱导剂和巨噬细胞的激活剂。 研究发现结合甲酰基肽的受体存在于吞噬性中性粒细胞上,并且最近已在肠粘膜细胞上发现。

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

常规特殊物品

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Carlos José Correia Santana et al.
Biomolecules, 10(5) (2020-05-24)
In recent years, the number of new antimicrobial drugs launched on the market has decreased considerably even though there has been an increase in the number of resistant microbial strains. Thus, antimicrobial resistance has become a serious public health problem.
E Krump et al.
The Journal of biological chemistry, 272(2), 937-944 (1997-01-10)
Activation of polymorphonuclear leukocytes (PMN) by chemotactic peptides initiates a series of functional responses that serve to eliminate pathogens. The intermediate steps that link engagement of the chemoattractant receptor to the microbicidal responses involve protein kinases that have yet to
P M Lad et al.
Proceedings of the National Academy of Sciences of the United States of America, 82(3), 869-873 (1985-02-01)
Pertussis toxin inhibits the N-formyl-Met-Leu-Phe (fMet-Leu-Phe) mediated human neutrophil functions of enzyme release, superoxide generation, aggregation, and chemotaxis. As pertussis toxin modifies the GTP binding receptor-regulatory protein "Ni," the association of the fMet-Leu-Phe receptor with such a protein was further
Michael Hannigan et al.
Proceedings of the National Academy of Sciences of the United States of America, 99(6), 3603-3608 (2002-03-21)
Confocal imaging and time-lapsed videomicroscopy were used to study the directionality, motility, rate of cell movement, and morphologies of phosphoinositide 3-kinase gamma (PI3K)gamma(-/-) neutrophils undergoing chemotaxis in Zigmond chambers containing N-formyl-Met-Leu-Phe gradients. Most of the PI3Kgamma(-/-) neutrophils failed to translocate
Ildefonso M De la Fuente et al.
Nature communications, 10(1), 3690-3690 (2019-08-17)
Associative memory is the main type of learning by which complex organisms endowed with evolved nervous systems respond efficiently to certain environmental stimuli. It has been found in different multicellular species, from cephalopods to humans, but never in individual cells.

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