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H1637

Sigma-Aldrich

cis-4-Hydroxy-L-proline

collagen synthesis inhibitor

Synonym(s):

(2S,4S)-(−)-4-Hydroxy-2-pyrrolidinecarboxylic acid, CHP

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About This Item

Empirical Formula (Hill Notation):
C5H9NO3
CAS Number:
618-27-9
Molecular Weight:
131.13
Beilstein:
81440
EC Number:
210-542-1
MDL number:
MFCD00064319
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24895470
NACRES:
NA.26

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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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.

Storage Class Code

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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