α-MSH的拮抗剂，降低黑色素的合成，诱导表皮细胞中的黑色素含量减少
编号：160658
CAS号：87616-84-0
单字母：H2N-HwAWfK-NH2
| 编号: | 160658 |
| 中文名称: | 生长激素释放肽-6/六肽-2、GHRP-6/Hexapeptide-2 |
| 中文同义词: | 醋酸生长激素释放肽-6;生长激素释放肽-6;醋酸生长激素释放肽-6GHRP-6ACETATE;醋酸生长激素释放肽-68Chemicalbook7616-84-0;生长激素释放肽-6醋酸生长激素释放肽-6;六肽-2/GHRP-6;六肽-2/GHRP-6/寡肽-24 |
| 英文名: | GHRP-6/Hexapeptide-2 |
| CAS号: | 87616-84-0 |
| 单字母: | H2N-HwAWfK-NH2 |
| 三字母: | H2N N端氨基 -His组氨酸 -DTrpD型色氨酸 -Ala丙氨酸 -Trp色氨酸 -DPheD型笨丙氨酸 -Lys赖氨酸 -NH2C端酰胺化 |
| 氨基酸个数: | 6 |
| 分子式: | C46H56N12O6 |
| 平均分子量: | 873.01 |
| 精确分子量: | 872.44 |
| 等电点(PI): | - |
| pH=7.0时的净电荷数: | 2.21 |
| 酸性基团个数: | 2.1 |
| 碱性基团个数: | 疏水 |
| 平均亲水性: | -1.2166666666667 |
| 疏水性值: | -0.72 |
| 外观与性状: | 白色粉末状固体 |
| 消光系数: | 11000 |
| 来源: | 人工化学合成，仅限科学研究使用，不得用于人体。 |
| 纯度: | 95%、98% |
| 储存条件: | 负80℃至负20℃ |
| 标签: | D型氨基酸肽 现货美容肽(Cosmetic peptides) |
In search of competitive β-MSH antagonists, the hexapeptide GHRP-6 has been recognized as a selective inhibitor of β-MSH activity in the frog skin bioassay. It is identical in sequence with a growth hormone-releasing peptide analog, (His¹,Lys⁶)-GHRP, which selectively releases GH in vitro and in a wide variety of species in vivo. GHRP-6 also acts as a functional antagonist of somatostatin in the somatotrope cells.
很多蛋白在细胞中非常容易被降解，或被标记，进而被选择性地破坏。但含有部分D型氨基酸的多肽则显示了很强的抵抗蛋白酶降解能力。
| 编号 | 产品名称（中文） | 产品名称（英文） | CAS NO |
| 棕榈酰二肽-18 | 棕榈酰二肽-18 | N/A | |
| 乙酰基二肽-1 鲸蜡酯 | Acetyl Dipeptide-1 cetyl ester | 196604-48-5 | |
| 乙酰二肽-3氨基己酸酯 | Acetyl dipeptide-3 aminohexanoate | 1265905-30-3 | |
| 二肽-2 | Dipeptide-2 | 24587-37-9 | |
| 二肽-6 | Dipeptide-6 | 18684-24-7 | |
| 类蛇毒三肽AKE | Syn-AKE(Dipetide diaminobutyroyl Benzylamide diacetate) | 823202-99-9 | |
| 生物素三肽-1 | Biotinoyl Tripeptide-1 | 299157-54-3 | |
| 乙酰三肽-1 | Acetyl Tripeptide-1 | N/A | |
| 三肽-1铜 | Copper peptide | 89030-95-5 | |
| 三肽-1 | Tripeptide-1 | 72957-37-0 | |
| 三肽-2 | Trifluoroacetyl Tripeptide-2 | 64577-63-5 | |
| 三肽-10瓜氨酸 | Tripeptide-10 Citrulline | 960531-53-7 | |
| 三肽-29 | Tripeptide-29 | 2239-67-0 | |
| 三肽-32 | Tripeptide-32 | N/A | |
| 三氟乙酰三肽-2 | Trifluoroacetyl Tripeptide-2 | 64577-63-5 | |
| 棕榈酰三肽-1 | Palmitoyl Tripeptide-1 | 147732-56-7 | |
| 棕榈酰三肽-5 | Palmitoyl Tripeptide-5 | 623172-56-5 | |
| 棕榈酰三肽-8 | Palmitoyl Tripeptide-8 | N/A | |
| 棕榈酰四肽-7 | Palmitoyl Tetrapeptide-7 | 221227-05-0 | |
| 己酰基四肽-3 | Caprooyl Tetrapeptide-3 | 1012317-71-3 | |
| 乙酰基四肽-2 | Acetyl Tetrapeptide-2 | N/A | |
| 乙酰基四肽-3 | Acetyl Tetrapeptide-3 | 827306-88-7 | |
| 乙酰基四肽-5 | Acetyl Tetrapeptide-5 | 820959-17-9 | |
| 乙酰基四肽-9 | Acetyl Tetrapeptide-9 | N/A | |
| 乙酰基四肽-11 | Acetyl Tetrapeptide-11 | 928006-88-6 | |
| 乙酰基四肽-15 | Acetyl Tetrapeptide-15 | 928007-64-1 | |
| 乙酰基四肽-22 | Acetyl Tetrapeptide-22 | N/A | |
| 乙酰基四肽-40 | Acetyl Tetrapeptide-40 | N/A | |
| 四肽-4 | Tetrapeptide-4 | N/A | |
| 四肽-21 | Tetrapeptide-26 | N/A | |
| 四肽-26 | Tetrapeptide-26 | N/A | |
| 四肽-30 | Tetrapeptide-30 | 1228558-05-1 | |
| 肉豆蔻四肽-12 | Myristoyl Tetrapeptide-12 | 959610-24-3 | |
| 棕榈酰五肽-4 | Palmitoyl Pentapeptide-4 | 214047-00-4 | |
| 肉豆蔻酰五肽-4 | Myristoyl Pentapeptide-4 | N/A | |
| 肉豆蔻酰五肽-8 | Myristoyl Pentapeptide-8 | N/A | |
| 肉豆蔻酰五肽-17 | Myristoyl Pentapeptide-17 | 959610-30-1 | |
| 五肽-3 | Pentapeptide-3 | 135679-88-8 | |
| 五肽-18 | Pentapeptide-18 | 64963-01-5 | |
| 五肽-25 | Pentapeptide-25 | N/A | |
| 乙酰基六肽-1 | Acetyl Hexapeptide-1 | 448944-47-6 | |
| 乙酰基六肽-8 | Acetyl Hexapeptide-8 | 616204-22-9 | |
| 乙酰基六肽-38 | Acetyl Hexapeptide-38 | N/A | |
| 乙酰基六肽-49 | Acetyl Hexapeptide-49 | N/A | |
| 棕榈酰六肽-12 | Palmitoyl Hexapeptide-12 | 171263-26-6 | |
| 棕榈酰六肽-14 | Palmitoyl Hexapeptide-14 | N/A | |
| 肉豆蔻酰六肽-5 | Myristoyl Hexapeptide-5 | N/A | |
| 肉豆蔻酰六肽-16 | Myristoyl Hexapeptide-16 | 959610-54-9 | |
| 肉豆蔻酰六肽-23 | Myristoyl Hexapeptide-23 | N/A | |
| 六肽-1 | Hexapeptide-1 | N/A | |
| 六肽-2 | Hexapeptide-2 | 87616-84-0 | |
| 六肽-3 | Hexapeptide-3 | ||
| 六肽-9 | Hexapeptide-9 | 1228371-11-6 | |
| 六肽-10 | Hexapeptide-10 | 146439-94-3 | |
| 六肽-11 | Hexapeptide-11 | 161258-30-6 | |
| 六肽-33 | Hexapeptide-33 | N/A | |
| 八肽-2 | Octapeptide-2 | N/A | |
| 乙酰基八肽-2 | Acetyl Octapeptide-2 | N/A | |
| 乙酰基八肽-3 | Acetyl Octapeptide-3(Snap-8) | 868844-74-0 | |
| 八肽-45 | Octapeptide-2 | N/A | |
| 九肽-1 | Nonapeptide-1 | 158563-45-2 | |
| 肉豆蔻酰九肽-3 | Myristoyl nonapeptide-3 | N/A | |
| 十肽-12 | Decapeptide-12 | N/A | |
| 寡肽-2 | Oligopeptide-2 | N/A | |
| 寡肽-3 | Oligopeptide-3 | N/A | |
| 寡肽-24 | Oligopeptide-24 | N/A | |
| 寡肽-54 | Oligopeptide-54 | N/A |
| DOI | 名称 | |
|---|---|---|
| 10.1016/j.cardiores.2003.10.012 | Growth hormone-releasing peptide can improve left ventricular dysfunction and attenuate dilation in dilated cardiomyopathic hamsters | 下载 |
| 10.1111/j.1365-2982.2004.00564.x | Effect of ghrelin and growth hormone-releasing peptide 6 on septic ileus in mice | 下载 |
| 10.1016/j.domaniend.2006.11.005 | Effects of ghrelin and its analogues on chicken ovarian granulosa cells | 下载 |
| 10.1208/pt0802043 | Formation of acylated growth hormone-releasing peptide-6 by poly(lactide-co-glycolide) and its biological activity | 下载 |
| 10.1016/j.ijpharm.2007.06.005 | In vitro release study of mono-PEGylated growth hormone-releasing peptide-6 from PLGA microspheres | 下载 |
| 10.1530/EJE-07-0659 | Association between tumoral GH-releasing peptide receptor type 1a mRNA expression and in vivo response to GH-releasing peptide-6 in ACTH-dependent Cushing's syndrome patients | 下载 |
| 10.1124/mol.108.049189 | Overlapping binding site for the endogenous agonist, small-molecule agonists, and ago-allosteric modulators on the ghrelin receptor | 下载 |
| 10.1530/EJE-09-0459 | Partial restoration of GH responsiveness to ghrelin in Cushing's disease after 6 months of ketoconazole treatment: comparison with GHRP-6 and GHRH | 下载 |
| 10.1016/0024-3205(90)90563-7 | Oral activity of the growth hormone releasing peptide His-D-Trp-Ala-Trp-D-Phe-Lys-NH2 in rats, dogs and monkeys | 下载 |
| 10.1016/j.mce.2011.02.002 | Insulin and growth hormone-releasing peptide-6 (GHRP-6) have differential beneficial effects on cell turnover in the pituitary, hypothalamus and cerebellum of streptozotocin (STZ)-induced diabetic rats | 下载 |
| 10.1016/j.peptides.2011.07.026 | Molecular identification of ghrelin receptor (GHS-R1a) and its functional role in the gastrointestinal tract of the guinea-pig | 下载 |
| 10.1210/en.2014-1074 | The opposing effects of ghrelin on hypothalamic and systemic inflammatory processes are modulated by its acylation status and food intake in male rats | 下载 |
| 10.1016/0028-3908(89)90129-9 | Binding of a growth hormone releasing hexapeptide to specific hypothalamic and pituitary binding sites | 下载 |
| 10.1111/j.1365-2826.2005.01347.x | Growth hormone-releasing peptide-6 increases insulin-like growth factor-I mRNA levels and activates Akt in RCA-6 cells as a model of neuropeptide Y neurones | 下载 |
多肽H2N-His-DTrp-Ala-Trp-DPhe-Lys-NH2的合成步骤：
1、合成MBHA树脂：取若干克的MBHA树脂（如初始取代度为0.5mmol/g）和1倍树脂摩尔量的Fmoc-Linker-OH加入到反应器中，加入DMF，搅拌使氨基酸完全溶解。再加入树脂2倍量的DIEPA，搅拌混合均匀。再加入树脂0.95倍量的HBTU，搅拌混合均匀。反应3-4小时后，用DMF洗涤3次。用2倍树脂体积的10%乙酸酐/DMF 进行封端30分钟。然后再用DMF洗涤3次，甲醇洗涤2次，DCM洗涤2次，再用甲醇洗涤2次。真空干燥12小时以上，得到干燥的树脂{Fmoc-Linker-MHBA Resin}，测定取代度。这里测得取代度为 0.3mmol/g。结构如下图：
2、脱Fmoc：取2.83g的上述树脂，用DCM或DMF溶胀20分钟。用DMF洗涤2遍。加3倍树脂体积的20%Pip/DMF溶液，鼓氮气30分钟，然后2倍树脂体积的DMF 洗涤5次。得到 H2N-Linker-MBHA Resin 。（此步骤脱除Fmoc基团，茚三酮检测为蓝色，Pip为哌啶）。结构图如下：
3、缩合：取2.55mmol Fmoc-Lys(Boc)-OH 氨基酸，加入到上述树脂里，加适当DMF溶解氨基酸，再依次加入5.09mmol DIPEA，2.42mmol HBTU。反应30分钟后，取小样洗涤，茚三酮检测为无色。用2倍树脂体积的DMF 洗涤3次树脂。（洗涤树脂，去掉残留溶剂，为下一步反应做准备）。得到Fmoc-Lys(Boc)-Linker-MBHA Resin。氨基酸：DIPEA：HBTU：树脂=3：6：2.85：1（摩尔比）。结构图如下：
4、依次循环步骤二、步骤三，依次得到
H2N-Lys(Boc)-Linker-MBHA Resin
Fmoc-DPhe-Lys(Boc)-Linker-MBHA Resin
H2N-DPhe-Lys(Boc)-Linker-MBHA Resin
Fmoc-Trp(Boc)-DPhe-Lys(Boc)-Linker-MBHA Resin
H2N-Trp(Boc)-DPhe-Lys(Boc)-Linker-MBHA Resin
Fmoc-Ala-Trp(Boc)-DPhe-Lys(Boc)-Linker-MBHA Resin
H2N-Ala-Trp(Boc)-DPhe-Lys(Boc)-Linker-MBHA Resin
Fmoc-DTrp(Boc)-Ala-Trp(Boc)-DPhe-Lys(Boc)-Linker-MBHA Resin
H2N-DTrp(Boc)-Ala-Trp(Boc)-DPhe-Lys(Boc)-Linker-MBHA Resin
Fmoc-His(Trt)-DTrp(Boc)-Ala-Trp(Boc)-DPhe-Lys(Boc)-Linker-MBHA Resin
以上中间结构，均可在专肽生物多肽计算器-多肽结构计算器中，一键画出。
最后再经过步骤二得到 H2N-His(Trt)-DTrp(Boc)-Ala-Trp(Boc)-DPhe-Lys(Boc)-Linker-MBHA Resin，结构如下：
5、切割：6倍树脂体积的切割液（或每1g树脂加8ml左右的切割液），摇床摇晃 2小时，过滤掉树脂，用冰无水乙醚沉淀滤液，并用冰无水乙醚洗涤沉淀物3次，最后将沉淀物放真空干燥釜中，常温干燥24小试，得到粗品H2N-His-DTrp-Ala-Trp-DPhe-Lys-NH2。结构图见产品结构图。
切割液选择：1）TFA：H2O=95%：5%
2）TFA：H2O：TIS=95%：2.5%：2.5%
3）三氟乙酸：茴香硫醚：1，2-乙二硫醇：苯酚：水=87.5%：5%：2.5%：2.5%：2.5%
（前两种适合没有容易氧化的氨基酸，例如Trp、Cys、Met。第三种适合几乎所有的序列。）
6、纯化冻干：使用液相色谱纯化，收集目标峰液体，进行冻干，获得蓬松的粉末状固体多肽。不过这时要取小样复测下纯度 是否目标纯度。
7、最后总结：
杭州专肽生物技术有限公司（ALLPEPTIDE https://www.allpeptide.com）主营定制多肽合成业务，提供各类长肽，短肽，环肽，提供各类修饰肽，如：荧光标记修饰（CY3、CY5、CY5.5、CY7、FAM、FITC、Rhodamine B、TAMRA等），功能基团修饰肽（叠氮、炔基、DBCO、DOTA、NOTA等），同位素标记肽（N15、C13），订书肽（Stapled Peptide）,脂肪酸修饰肽（Pal、Myr、Ste），磷酸化修饰肽（P-Ser、P-Thr、P-Tyr），环肽（酰胺键环肽、一对或者多对二硫键环），生物素标记肽，PEG修饰肽，甲基化修饰肽等。
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