L-Proline ethyl ester hydrochloride
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L-Proline ethyl ester hydrochloride

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Category
Cyclic Amino Acids
Catalog number
BAT-003444
CAS number
33305-75-8
Molecular Formula
C7H13NO2·HCl
Molecular Weight
179.65
L-Proline ethyl ester hydrochloride
Synonyms
L-Pro-OEt HCl; (S)-Pyrrolidine-2-carboxylic acid ethyl ester; L-proline ethyl ester monohydrochloride; (S)-ethyl pyrrolidine-2-carboxylate hydrochloride; ethyl(2S)-2-pyrrolidinecarboxylate hydrochloride; L-proline ethyl ester hydrochloride; L-Pro-Oet HCl
Purity
≥ 95%
Density
g/cm3
Storage
Store at 2-8 °C
InChI
InChI=1S/C7H13NO2.ClH/c1-2-10-7(9)6-4-3-5-8-6;/h6,8H,2-5H2,1H3;1H/t6-;/m0./s1
InChI Key
DUJGQVVONTYHLT-RGMNGODLSA-N
Canonical SMILES
CCOC(=O)C1CCCN1.Cl
1. Inhibition of human hepatocellular carcinoma by L-proline-m-bis (2-chloroethyl) amino-L-phenylalanyl-L-norvaline ethyl ester hydrochloride (MF13) in vitro and in vivo
Qiong-Ying Hu, Jian-Nong Li, Dan-Qing Song, Yan-Ling Wang, George Bekesi, Imre Weisz, Jian-Dong Jiang Int J Oncol. 2004 Nov;25(5):1289-96.
A new anticancer tripeptide, L-proline-m-bis (2-chloroethyl) amino-L-phenylalanyl-L-norvaline ethyl ester hydrochloride (MF13), was investigated for its activity and mechanism in human hepatocellular carcinoma (HCC) cell lines. MF13 showed antiproliferative activities in the panel of 7 human HCC cell lines with IC50 in the range of 0.08-2.32 microM. A significant blockade in the S-phase occurred in tumor cells 12 h after their exposure to MF13. The inactivated Rb (phosphorylated Rb, pRb), which is present in the S-phase, was increased within 6 h of treatment. Bcl-2 expression was without change in hepatocarcinoma cells treated with MF13; however, a significant increase of bax was observed, resulting in a decreased ratio of bcl-2/bax. Increased activity of caspase-9, -8 and -3 was detected in the MF13 treated cells, indicating an activated pathway of apoptosis by MF13. Morphological examination as well as DNA gel electrophoresis demonstrated a nuclear fragmentation and DNA degradation in the form of multiple-unit DNA ladder in MF13 treated tumor cells. MF13 alone at 10 mg/kg (i.p.) inhibited HepG2 tumor in nude mice by more than 94% in volume. Bel-7402 tumor originated from a Chinese patient with HCC exhibited a sensitivity to MF13 similar to HepG2 in vivo. Antitumor effect of MF13 in the nude mice bearing human hepatocarcinoma (Bel-7402 or HepG2) was stronger than mitomycin C as well as its precursor m-sarcolysin (p<0.01), and comparable with cyclophosphamide. We believe MF13 merits consideration for further investigation as an agent against human hepatocellular carcinoma.
2. High anticancer efficacy of L-proline-m-bis (2-chloroethyl) amino-L-phenylalanyl-L-norvaline ethyl ester hydrochloride (MF13) in vivo
J D Jiang, H Zhang, J N Li, J Roboz, W B Qiao, J F Holland, G Bekesi Anticancer Res. 2001 May-Jun;21(3B):1681-9.
The anticancer efficacy of the new anticancer tripeptide, L-proline-m-bis (2-chloroethyl) amino-L-phenylalanyl-L-norvaline ethyl ester hydrochloride (MF13), was investigated in mice. MF13 showed a therapeutic effect in liquid tumors and induced complete remission even in late stage malignancies. MF13 also inhibited human colon cancer growth in nude mice by more than 85% (volume, p<0.001). It acted in a dose-dependent manner and induced a complete regression of tumor in 20% of the mice when the initial dose was high (15 mg/kg, i.p.). Human melanoma exhibited a response to MF13 similar to colon cancer. Activity of MF13 in murine hepatoma in vivo was stronger than its precursor m-sarcolysin (p<0.001). Tumor cells in peritoneal cavities of the MF13 treated (s.c.) mice underwent an irreversible apoptosis. Side effects of MF13 were the transient depression of hemopoiesis and loss of body weight, which vanished within 9-10 days. LD50 of MF13 of a single i.p. injection was 27 mg/kg (94 mg/m2), 11 times higher than the therapeutic dose of a single injection.
3. Investigation of d-Amino Acid-Based Surfactants and Nanocomposites with Gold and Silica Nanoparticles as against Multidrug-Resistant Bacteria Agents
Jae Ho Shim, Sungduk Gwak, Byung Kook Ahn, Hogyu Han, Yeonsun Hong, Ok Sarah Shin ACS Omega. 2022 Dec 8;7(50):46146-46155. doi: 10.1021/acsomega.2c04220. eCollection 2022 Dec 20.
d-amino acid-based surfactants (d-AASs) were synthesized and their antimicrobial activity was evaluated. N-α-lauroyl-d-arginine ethyl ester hydrochloride (d-LAE), d-proline dodecyl ester (d-PD), and d-alanine dodecyl ester (d-AD) were found to have antibacterial activity against both Gram-positive and -negative bacteria, but less efficacy against Gram-negative bacteria. For these reasons, combining antimicrobial agents with nanoparticles is a promising technique for improving their antibacterial properties to eliminate drug-resistant pathogens. d-LAE coated on gold (AuNP) and silica (SiNP) nanoparticles has more efficient antibacterial activity than that of d-LAE alone. However, unlike d-LAE, d-PD has enhanced antibacterial activity upon being coated on AuNP. The antibacterial d-AASs and their nanocomposites with nanoparticles were synthesized in an environmentally friendly manner and are expected to be valuable new antimicrobial agents against multidrug-resistant (MDR) pathogens.
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