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H1637

Sigma-Aldrich

顺式-4-羟基-L-脯氨酸

collagen synthesis inhibitor

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别名:
(2S,4S)-(-)-4-羟基-2-吡咯烷羧酸, CHP
经验公式（希尔记法）:
C5H9NO3
CAS号:
618-27-9
分子量:
131.13
Beilstein:
81440
EC 号:
210-542-1
MDL编号:
MFCD00064319
eCl@ss:
32160406
PubChem化学物质编号:
24895470
NACRES:
NA.26

质量水平

100

检测方案

≥98% (TLC)

形式

powder

technique(s)

ligand binding assay: suitable

颜色

white to faint yellow

mp

257 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

O[C@@H]1CN[C@@H](C1)C(O)=O

InChI

1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1

InChI key

PMMYEEVYMWASQN-IMJSIDKUSA-N

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相关类别

应用

顺式-4-羟基-L-脯氨酸（CHP）是一种可抑制胶原蛋白的合成并已被用作抗癌化合物的脯氨酸类似物。CHP阻断了C2C12鼠骨骼肌细胞中肌管的形成和肌节肌球蛋白重链的表达。CHP抑制了鼠Panc02胰腺癌细胞系和大鼠胰腺癌细胞DSL6A的增殖。

生化/生理作用

顺式-4-羟基-L-脯氨酸（CHP）及其衍生物可能具有抗癌活性。顺式-4-羟基-L-脯氨酸和其他羟基-L-脯氨酸是潜在药物手性合成的重要中间体。

其他说明

鹅膏肽毒素而非如胶原蛋白等动物蛋白的组成成分。

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

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Christoph Mueller et al.
World journal of gastroenterology, 12(10), 1569-1576 (2006-03-30)
To investigate the biological effects of cis-hydroxyproline (CHP) on the rat pancreatic carcinoma cell line DSL6A, and to examine the underlying molecular mechanisms. The effect of CHP on DSL6A cell proliferation was assessed by using BrdU incorporation. The expression of
Heather Dickens et al.
Molecular medicine reports, 1(4), 459-464 (2008-07-01)
cis-4-Hydroxy-L-proline (CHP) is being clinically evaluated as an anticancer drug. Since this compound targets the production of L-proline-rich proteins and critical L-proline residues, its impact on long-term cultures of human hepatocytes and toxicity in rats was studied to investigate possible
Ryotaro Hara et al.
Biochemical and biophysical research communications, 379(4), 882-886 (2009-01-10)
Hydroxyprolines are valuable chiral building blocks for organic synthesis of pharmaceuticals. Several microorganisms producing L-proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hydroxy-L-proline, respectively. Meanwhile, other hydroxyproline isomers, cis-4- and
Dietrich Sturm et al.
International journal of colorectal disease, 25(8), 921-929 (2010-04-21)
This study addressed the question of whether the collagen metabolism modulator cis-4-Hydroxy-L-proline (CHP) is applicable for potential use as a therapeutic inhibitor of pancreatic carcinoma cell growth. Cell proliferation, as well as quantification of apoptosis of murine Panc02 cells, was
Linda Metzner et al.
The Journal of pharmacology and experimental therapeutics, 309(1), 28-35 (2004-01-14)
Several proline derivatives such as L-azetidine-2-carboxylic acid, cis-4-hydroxy-L-proline, and 3,4-dehydro-DL-proline prevent procollagen from folding into a stable triple-helical conformation, thereby reducing excessive deposition of collagen in fibrotic processes and the growth of tumors. This study was performed to investigate whether
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