H1637
cis-4-Hydroxy-L-proline
collagen synthesis inhibitor
Sinônimo(s):
(2S,4S)-(−)-4-Hydroxy-2-pyrrolidinecarboxylic acid, CHP
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About This Item
Fórmula empírica (Notação de Hill):
C5H9NO3
Número CAS:
Peso molecular:
131.13
Beilstein:
81440
Número CE:
Número MDL:
Código UNSPSC:
12352209
eCl@ss:
32160406
ID de substância PubChem:
NACRES:
NA.26
Produtos recomendados
Nível de qualidade
Ensaio
≥98% (TLC)
Formulário
powder
técnica(s)
ligand binding assay: suitable
cor
white to faint yellow
pf
257 °C (dec.) (lit.)
aplicação(ões)
peptide synthesis
cadeia de caracteres SMILES
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
chave InChI
PMMYEEVYMWASQN-IMJSIDKUSA-N
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Aplicação
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.
Ações bioquímicas/fisiológicas
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.
Outras notas
Constituent of Amanita sp. peptide toxins but not of animal proteins like collagen.
Código de classe de armazenamento
11 - Combustible Solids
Classe de risco de água (WGK)
WGK 3
Ponto de fulgor (°F)
Not applicable
Ponto de fulgor (°C)
Not applicable
Equipamento de proteção individual
Eyeshields, Gloves, type N95 (US)
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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
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
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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