N-Boc-Phe-Leu-Phe-Leu-Phe
(Synonyms: Boc-FLFLF) 目录号 : GC36706
N-Boc-Phe-Leu-Phe-Leu-Phe是一种甲酰肽受体（FPR）1拮抗剂，表观解离常数KD为230nM。
Cas No.:148182-34-7
Sample solution is provided at 25 µL, 10mM.
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N-Boc-Phe-Leu-Phe-Leu-Phe is an antagonist of formyl peptide receptor (FPR) 1, with the apparent dissociation constant KD of 230nM[1]. N-Boc-Phe-Leu-Phe-Leu-Phe inhibits neutrophil chemotaxis induced by FPR1, and suppresses the production of superoxide[2]. N-Boc-Phe-Leu-Phe-Leu-Phe has been widely used as a model compound to develop a series of derivatives and is employed as a positron emission tomography imaging agent[1,3].
In vitro, N-Boc-Phe-Leu-Phe-Leu-Phe treatment at 120μM for 48h inhibited VEGF-A165-mediated human umbilical vein endothelial cell (HUVEC) proliferation and blocked the activation of the downstream secondary signaling mediators EKR1/2 and AKT[4]. Treatment of rat conjunctival goblet cells with N-Boc-Phe-Leu-Phe-Leu-Phe (0.1mM) for 30 minutes would affect the intracellular calcium ion concentration regulated by Maresin 2 and reduce the response of lipoxin (LX) A4[5].
In, vivo, N-Boc-Phe-Leu-Phe-Leu-Phe treatment via intraperitoneal injections (1mg/kg) twice a week for 8 weeks significantly inhibited the anti-fibrotic effect of Ac2-26 in mice with liver fibrosis and promoted liver inflammation induced by CCl4[6]. Intraperitoneal injection of N-Boc-Phe-Leu-Phe-Leu-Phe (1μl; 10mM) every other day for 6 consecutive days can block the renal injury repair effect of BML-111 in the diabetic mouse model[7].
References:
[1] Hayashi R, Kitajima T, Mizuguchi H, et al. Development of potent antagonists for formyl peptide receptor 1 based on Boc-Phe-D-Leu-Phe-D-Leu-Phe-OH[J]. Bioorganic & Medicinal Chemistry, 2014, 22(15): 3824-3828.
[2] Stenfeldt A L, Karlsson J, Wennerås C, et al. Cyclosporin H, Boc-MLF and Boc-FLFLF are antagonists that preferentially inhibit activity triggered through the formyl peptide receptor[J]. Inflammation, 2007, 30(6): 224-229.
[3] Dalpiaz A, Ferretti M E, Vertuani G, et al. C-and N-terminal residue effect on peptide derivatives' antagonism toward the formyl-peptide receptor[J]. European journal of pharmacology, 2002, 436(3): 187-196.
[4] Nawaz I M, Chiodelli P, Rezzola S, et al. N-tert-butyloxycarbonyl-Phe-Leu-Phe-Leu-Phe (BOC2) inhibits the angiogenic activity of heparin-binding growth factors[J]. Angiogenesis, 2018, 21(1): 47-59.
[5] Olsen M V, Lyngstadaas A V, Bair J A, et al. Signaling pathways used by the specialized pro-resolving mediator maresin 2 regulate goblet cell function: Comparison with maresin 1[J]. International journal of molecular sciences, 2022, 23(11): 6233.
[6] Fan J H, Luo N, Liu G F, et al. Mechanism of annexin A1/N-formylpeptide receptor regulation of macrophage function to inhibit hepatic stellate cell activation through Wnt/β-catenin pathway[J]. World Journal of Gastroenterology, 2023, 29(22): 3422.
[7] Hao H, Xie F, Xu F, et al. LipoxinA4 analog BML-111 protects podocytes cultured in high-glucose medium against oxidative injury via activating Nrf2 pathway[J]. International Immunopharmacology, 2022, 111: 109170.
N-Boc-Phe-Leu-Phe-Leu-Phe是一种甲酰肽受体（FPR）1拮抗剂，表观解离常数KD为230nM[1]。N-Boc-Phe-Leu-Phe-Leu-Phe可抑制FPR1诱导的中性粒细胞趋化作用，并抑制超氧化物的产生[2]。N-Boc-Phe-Leu-Phe-Leu-Phe模型先导化合物被广泛用于开发一系列衍生物，并作为正电子发射断层扫描成像剂使用[1,3]。
在体外，120μM的N-Boc-Phe-Leu-Phe-Leu-Phe处理48小时可抑制VEGF-A165介导的人脐静脉内皮细胞(HUVEC)增殖，并阻断下游信号介质ERK1/2和AKT的激活[4]。0.1mM的N-Boc-Phe-Leu-Phe-Leu-Phe处理大鼠结膜杯状细胞30分钟会影响Maresin 2调控的细胞内钙离子浓度，并降低脂毒素（LX）A4的响应[5]。
在体内，肝纤维化小鼠每周两次腹腔注射N-Boc-Phe-Leu-Phe-Leu-Phe（1mg/kg；持续8周）可显著抑制Ac2-26的抗纤维化作用，并促进CCl4诱导的肝脏炎症[6]。糖尿病小鼠模型隔日腹腔注射N-Boc-Phe-Leu-Phe-Leu-Phe（1μl; 10mM；持续6天）能阻断BML-111的肾损伤修复作用[7]。
| Cell experiment [1]: | |
Cell lines | Human umbilical vein endothelial cells (HUVECs) |
Preparation Method | HUVECs were cultured on a plate coated with porcine gelatin, in M199 medium supplemented with 20% FCS, endothelial cell growth factor (10μg/mL) and porcine heparin (100μg/mL). The cells were cultured in a humidified 37°C incubator with 5% CO2. The medium was changed every 2-3 days until the cells reached confluence. HUVECs were seeded at a density of 1.7 × 104 cells/cm2 and incubated under serum starvation conditions overnight. Then, in the presence of 2.5% FCS, the cells were treated with 30ng/mL VEGF-A165 and increasing concentrations of N-Boc-Phe-Leu-Phe-Leu-Phe (0, 3, 7.5, 15, 30, 60, and 120μM) to stimulate the cells. After 48 hours, the cells were counted using a fluorescence counter. |
Reaction Conditions | 0, 3, 7.5, 15, 30, 60, and 120μM; 48h |
Applications | N-Boc-Phe-Leu-Phe-Leu-Phe treatment significantly inhibited VEGF-A165-mediated HUVEC proliferation in a dose-dependent manner. |
| Animal experiment [2]: | |
Animal models | C57BL/6 mice |
Preparation Method | Six to eight-week-old C57BL/6 mice (weighing 18-25g) were raised in a constant temperature and humidity room with a 12-hour day-night cycle. Thirty-two mice were randomly divided into four subgroups, with eight mice in each group: the control group, the CCl4-induced liver fibrosis group, the liver fibrosis + Ac2-26 group, and the liver fibrosis + Ac2-26 + N-Boc-Phe-Leu-Phe-Leu-Phe-Leu-Phe group. The control group mice were intraperitoneally injected with olive oil, and the other three subgroups were intraperitoneally injected twice a week with 20% CCl4 (500mL) and CCl4 + Ac2-26 at 1mg/kg, with or without N-Boc-Phe-Leu-Phe-Leu-Phe-Leu-Phe at 1mg/kg. At 8 weeks after injection, the mice were anesthetized with pentobarbital sodium (50mg/kg intravenous injection) and liver tissue samples were collected for analysis. |
Dosage form | 1mg/kg twice a week for 8 weeks; i.p. |
Applications | N-Boc-Phe-Leu-Phe-Leu-Phe-Leu-Phe treatment inhibited the anti-liver fibrosis effect of Ac2-26 and promoted the liver inflammation induced by CCl4 in mice. |
References: | |
| Cas No. | 148182-34-7 | SDF | |
| 别名 | Boc-FLFLF | ||
| 分子式 | C44H59N5O8 | 分子量 | 785.97 |
| 溶解度 | Water: < 0.1 mg/mL (insoluble) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.2723 mL | 6.3616 mL | 12.7231 mL |
| 5 mM | 254.5 μL | 1.2723 mL | 2.5446 mL |
| 10 mM | 127.2 μL | 636.2 μL | 1.2723 mL |
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| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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工作液浓度： mg/ml；
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2.
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