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Biosynthesis, chemical synthesis and application of nitrogen-containing aryl compounds.

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Abstract
Fenitrothion is a nitrophenolic pesticide with nitrogen-containing aryl structures that has been widely used in agriculture. However, the major hydrolysis metabolite of fenitrothion is toxic to many living organisms, raising environmental safety concerns. It is necessary and promising to remove fenitrothion from pesticide-polluted soil and water by biology methods. On the other hand, nitrogen-containing aryl structure is an important pharmacophore of anticancer drugs. In recent years, cancer has become the biggest threat to human health and the research of cancer drugs is particularly important.
The pesticide-binding peptide SPPWPPRP monomer and dimer were introduced respectively and displayed in E. coli, the binding efficiency under different temperatures, pH levels, and fenitrothion concentrations were evaluated. The recombinant strain with peptide dimer provided the highest amount of fenitrothion adsorption (136.0 µmol fenitrothion/g DCW), while the strain with the monomer adsorbed somewhat less (117.2 µmol fenitrothion/g DCW). The results indicated that the peptide-displaying recombinant strain can efficiently adsorb fenitrothion present in actual soil, and can be used to decontaminate fenitrothion-contaminated soil. All the tested E. coli strains remain intact under contaminated conditions.
Acid tolerance peptides DR1558 and ycgZ-ymgABC were introduced and displayed in E. coli, the GABA production under different pH levels was evaluated. Final GABA concentration was increased by 11.3% via the inactivation of competing pathways at initial MSG concentration of 10g/L. Both of DR1558 combined strain and ycgZ-ymgABC combined strain produced higher GBAB yields under relatively lower pH conditions, showing that the introduction of acid-tolerance peptides can help increase GABA production. However, conditions including temperature and initial MSG concentration need to be further optimized to achieve better GABA output.
1, 4-disubstituted-3,4-dihydroquinazolin-2(1H)-one derivatives and phenylpropionate compounds were synthesized, and their potential in cancer inhibition was evaluated by computer aided drug design (Discovery Studio) and tested in K562, A549, U251 and L02 cell lines by MTT assay. Among these synthesized quinazolinone derivatives, (S)-6-chloro-1-(cyclopropylmethyl)-4-(2-fluorophenyl)-3,4-dihydroquinazolin-2(1H)-one (12d) possessed more optimal antiproliferative activity with IC50 values lower than 30 μM. As for tested cell lines, better inhibition effect was implied on lung cancer cell A549.
Phenylpropionate compounds which considered to have good anti-tumor activity in the preliminary drug-assisted design were synthesizes through convenient routes. Active molecules of isothiourea with phenylalanine group were successfully synthesized. A multicomponent protocol that involves electrophilic center and isocyanide is proved to be suitable for the formation of these and other important isothiourea compounds, including an anti-gout drug and CXCR4 antibody. The advantages of mild reaction conditions, reduced purification steps, and ease of starting material accessibility is a useful addition to existing methodologies.
Author(s)
왕원원
Issued Date
2021
Awarded Date
2021-02
Type
Dissertation
URI
https://oak.ulsan.ac.kr/handle/2021.oak/5764
http://ulsan.dcollection.net/common/orgView/200000371582
Alternative Author(s)
YUANYUAN WANG
Affiliation
울산대학교
Department
일반대학원 생명화학공학과화학공학전공
Advisor
Soon-Ho Hong
Degree
Doctor
Publisher
울산대학교 일반대학원 생명화학공학과화학공학전공
Language
eng
Rights
울산대학교 논문은 저작권에 의해 보호받습니다.
Appears in Collections:
Chemical Engineering > 2. Theses (Ph.D)
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