H1637
顺式-4-羟基-L-脯氨酸
collagen synthesis inhibitor
别名:
(2S,4S)-(-)-4-羟基-2-吡咯烷羧酸, CHP
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关于此项目
经验公式（希尔记法）:
C5H9NO3
化学文摘社编号:
分子量:
131.13
NACRES:
NA.26
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
210-542-1
MDL number:
Beilstein/REAXYS Number:
81440
产品名称
顺式-4-羟基-L-脯氨酸, collagen synthesis inhibitor
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
SMILES string
O[C@@H]1CN[C@@H](C1)C(O)=O
assay
≥98% (TLC)
form
powder
technique(s)
ligand binding assay: suitable
color
white to faint yellow
mp
257 °C (dec.) (lit.)
application(s)
peptide synthesis
Quality Level
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Application
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。
Biochem/physiol Actions
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。
Other Notes
鹅膏肽毒素而非如胶原蛋白等动物蛋白的组成成分。
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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
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
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
Sevil Oskay Halacli et al.
Clinical immunology (Orlando, Fla.), 161(2), 316-323 (2015-06-29)
Combined immunodeficiencies (CIDs) are heterogeneous group of disorders characterized by abrogated/impaired T cell development and/or functions that resulted from diverse genetic defects. In addition to the susceptibility to infections with various microorganisms, the patients may have lymphoproliferation, autoimmunity, inflammation, allergy
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