Synthesis and structure modification of marine natural product caerulomycins for study anticancer activity

Name: Jesada Maneewong

LCSH: Burapha University -- Chemistry Faculty Of Science

Classification :.DDC: 547

LCSH: Natural products

LCSH: Caerulomycins

Abstract: Caerulomycin A, a marine natural product was isolated from the fermentation broth of Streptomyces caeruleus with antibiotic, antifungal, and cytotoxic activities. The structure of caerulomycin A contains a bipyridinic molecular as a core structure with a substituted oxime functional group. In the first part, we designed and synthesized of caerulomycin A and its analogues by a convenient and efficient method. The total synthesis of caerulomycin A was carried out via flexible method involving three important steps including amidation, intramolecular aldoltype condensation and oxidation reactions starting from commercially available reagents using metal-free catalyst. Caerulomycin A was employed as a precursor for further modification to new isoxazolyl caerulomycin analogues by using click reaction with various alkynes. Moreover, the second series of alkyl ether caerulomycin derivatives was synthesized via 4-hydroxyl bipyridine by using alkylation, oxidation, and condensation reactions respectively. All synthetic compounds were obtained in moderate to excellent yields under standard conditions. All the synthesized compounds were evaluated in vitro against seven cancer cell lines. The synthetic caerulomycin A derivatives exhibited cytotoxic activity in many cancer cell lines including the human intrahepatic cholangiocarcinoma (KKU-M213), human squamous cell carcinoma (FaDu), human colorectal adenocarcinoma (HT-29), human mammary gland/breast adenocarcinoma (MDA-MB-231), human lung carcinoma (A549), and human neuroblastoma (SH-SY5Y). The novel caerulomycin A derivatives can be used as lead compounds for drug development of anti-cancer agent in the future.

Burapha University. Library

Address: CHONBURI

Email: buulibrary@buu.ac.th

Name: Rungnapha Saeeng

Role: Principal advisor

Created: 2022

Modified: 2023-02-22

Issued: 2023-02-22

วิทยานิพนธ์/Thesis

application/pdf

CallNumber: Th 547 Je58S

eng

DegreeName: Master of Science

Level: Master's Degree

Descipline: Chemistry

Grantor: Burapha University

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