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5'-Amino-Modifier C12
5'-Amino Modifier is designed for use in automatic synthesizers to functionalize the sequence of the 5'end of the target oligonucleotide. The use of trityl-protected amino-modifiers is recommended when purification is required prior to use.
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Catalog
BRP-02216
Synonyms
5'-Amino-Modifier C12-MMTr CE Phosphoramidite; 12-(4-Monomethoxytritylamino)dodecyl-1-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite; Phosphoramidous acid, N,N-bis(1-methylethyl)-, 2-cyanoethyl 12-[[(4-methoxyphenyl)diphenylmethyl]amino]dodecyl ester; MMT-C12-amine-linker Phosphoramidite; Monomethoxytrityl-C12-hexylamine-linker Phosphoramidite; 5'-Amino-Modifier C12 Phosphoramidite; 2-Cyanoethyl 12-[[(4-methoxyphenyl)diphenylmethyl]amino]dodecyl N,N-bis(1-methylethyl)phosphoramidite
CAS
178925-51-4
IUPAC Name
3-[[di(propan-2-yl)amino]-[12-[[(4-methoxyphenyl)-diphenylmethyl]amino]dodecoxy]phosphanyl]oxypropanenitrile
Molecular Weight
673.92
Molecular Formula
C41H60N3O3P
Canonical SMILES
CC(C)N(C(C)C)P(OCCCCCCCCCCCCNC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=C(C=C3)OC)OCCC#N
InChI
InChI=1S/C41H60N3O3P/c1-35(2)44(36(3)4)48(47-34-22-31-42)46-33-21-13-11-9-7-6-8-10-12-20-32-43-41(37-23-16-14-17-24-37,38-25-18-15-19-26-38)39-27-29-40(45-5)30-28-39/h14-19,23-30,35-36,43H,6-13,20-22,32-34H2,1-5H3
InChIKey
VJLVUDQTXLCFHR-UHFFFAOYSA-N
Boiling Point
687.7±55.0 °C at 760 mmHg
Purity
>95%
Appearance
Light-yellow oily matter
Storage
Store at -20 °C
Formulation
Dilute with anhydrous acetonitrile
Chemical Structure:
Reference Reading
1. Epo-C12 inhibits peroxiredoxin 1 peroxidase activity
Tomoka Yoda, Masateru Furuta, Tomohiko Tsutsumi, Seiki Ikeda, Shunsuke Yukizawa, Satoshi Arai, Akinori Morita, Kenji Yamatoya, Kazuya Nakata, Shusuke Tomoshige, Kenji Ohgane, Yuuki Furuyama, Kengo Sakaguchi, Fumio Sugawara, Susumu Kobayashi, Masahiko Ikekita, Kouji Kuramochi. Bioorg Med Chem. 2021 Jul 1;41:116203. doi: 10.1016/j.bmc.2021.116203.
Epo-C12 is a synthetic derivative of epolactaene, isolated from Penicillium sp. BM 1689-P. Epo-C12 induces apoptosis in human acute lymphoblastoid leukemia BALL-1 cells. In our previous studies, seven proteins that bind to Epo-C12 were identified by a combination of pull-down experiments using biotinylated Epo-C12 (Bio-Epo-C12) and mass spectrometry. In the present study, the effect of Epo-C12 on peroxiredoxin 1 (Prx 1), one of the proteins that binds to Epo-C12, was investigated. Epo-C12 inhibited Prx 1 peroxidase activity. However, it did not suppress its chaperone activity. Binding experiments between Bio-Epo-C12 and point-mutated Prx 1s suggest that Epo-C12 binds to Cys52 and Cys83 in Prx 1. The present study revealed that Prx 1 is one of the target proteins through which Epo-C12 exerts an apoptotic effect in BALL-1 cells.
2. miR-F4-C12 Functions on the Regulation of Adipose Accumulation by Targeting PIK3R1 in Castrated Male Pigs
Qiao Xu, Jie Chen, Ximing Liu, Yabiao Luo, Tianzuo Wang, Meiying Fang. Animals (Basel). 2021 Oct 26;11(11):3053. doi: 10.3390/ani11113053.
MicroRNAs (miRNAs) constitute small regulatory molecules for a wide array of biological activities (18~24 nucleotides in length), including adipogenesis and adipose deposition. Their effect is, however, incompletely defined in inducing fat accumulation in castrated male pigs. Based on our study, four nine-times miRNAs were selected to examine their functions in adipose formation activities. In 3T3-L1 cells and backfat tissues of castrated and intact male pigs, miR-F4-C12 was identified as a factor in adipose development utilizing quantitative real-time PCR (qRT-PCR). Further, miR-F4-C12 was identified to promote fat development, suggesting that miR-F4-C12 was involved in adipogenesis. Moreover, phosphoinositide-3-kinase regulatory subunit 1 (PIK3R1) was proposed by the TargetScan, miRDB and starBase as a target of miR-F4-C12 and verified through a two-luciferase reporter assay. The over-expression of miR-F4-C12 dramatically decreases the PIK3R1 protein level in 3T3-L1 cells. The mRNA and protein levels of PIK3R1 in castrated pigs are reduced relative to intact pigs, providing further evidence that PIK3R1 is involved in regulating adipose accumulation. These results suggest that miR-F4-C12 involves adipose development and may regulate subcutaneous adipose tissue accumulation by targeting PIK3R1 in castrated male pigs.
3. 9-N-n-alkyl Berberine Derivatives: Hypoglycemic Activity Evaluation
Mikhail V Khvostov, Elizaveta D Gladkova, Sergey A Borisov, Marina S Fedotova, Nataliya A Zhukova, Mariya K Marenina, Yulia V Meshkova, Nicolae Valutsa, Olga A Luzina, Tatiana G Tolstikova, Nariman F Salakhutdinov. Pharmaceutics. 2022 Dec 22;15(1):44. doi: 10.3390/pharmaceutics15010044.
Several novel 9-N-n-alkyl derivatives of berberine (C5, C7, C10, C12) were synthesized. They were analyzed in vitro and in vivo for their hypoglycemic activity. In vitro studies showed that the derivatives with shorter alkyl substitutes at concentrations ranging from 2.5 to 10 μM were able to stimulate glucose consumption by HepG2 cells more prominently than the derivatives with longer substitutes (C10 and C12). All compounds demonstrated a better effect compared to berberine. Their impact on cells' viability also depended on the alkyl substitutes length, but in this case, C10 and C12 derivatives demonstrated the best results. A similar correlation was also found in the OGTT, where the C5 derivative demonstrated a pronounced hypoglycemic effect at a dose of 15 mg/kg and C12 was less effective. This compound was further investigated in C57BL/6Ay mice for four weeks and was administered at a dose of 15 mg/kg. Pronounced effect of C12 on carbohydrate metabolism in mice was discovered: there was a decrease in fasting glucose levels and an increase in glucose tolerance in OGTT on the 14th and 28th days of the experiment. However, at the end of the experiment, signs of hepatosis exacerbation and an increase in the content of hepatic aminotransferases in blood were found.
