H1637
cis-4-Hydroxy-L-proline
collagen synthesis inhibitor
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Synonym(s):
(2S,4S)-(−)-4-Hydroxy-2-pyrrolidinecarboxylic acid, CHP
Empirical Formula (Hill Notation):
C5H9NO3
CAS Number:
Molecular Weight:
131.13
Beilstein:
81440
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26
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Quality Level
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
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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Related Categories
Application
cis-4-Hydroxy-L-proline (CHP) is a proline analog that inhibits collagen synthesis and has been used as an anticancer compound. CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells. CHP inhibited proliferation of murine Panc02 pancreatic carcinoma cell line and rat pancreatic carcinoma cell line DSL6A.
Biochem/physiol Actions
cis-4-Hydroxy-L-proline (CHP) and its derivatives may have anticancer activity. cis-4-Hydroxy-L-proline and other hydrosyl-L-prolines are important intermediates for chiral synthesis of potential drugs.
Other Notes
Constituent of Amanita sp. peptide toxins but not of animal proteins like collagen.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
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
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
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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