Facile synthesis and biological evaluation of chrysin derivatives

被引:8
作者
Omonga, Nicholas [1 ]
Zia, Zakia [2 ]
Ghanbour, Hesham [1 ]
Ragazzon-Smith, Abby [3 ]
Foster, Howard [1 ]
Hadfield, John [1 ]
Ragazzon, Patricia [4 ]
机构
[1] Univ Salford, Biomed Res Ctr, Sch Sci Engn & Environm, Salford, Lancs, England
[2] Labcorp Clin Res Unit Ltd, Leeds, W Yorkshire, England
[3] Manchester Metropolitan Univ, Sch Sci & Environm, Manchester, Lancs, England
[4] Keele Univ, Sch Pharm & Bioengn, Hornbeam 2-26, Keele ST5 BG, Staffs, England
关键词
antibacterial; antifungal; chrysin derivatives; cytotoxicity; microwave; ANTIMICROBIAL RESISTANCE; INFECTION; APOPTOSIS; DESIGN; ENTEROBACTERIACEAE; MECHANISMS; FLAVONOIDS; CELLS;
D O I
10.1177/17475198211057467
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this paper, novel synthetic methods, including microwave O-alkylation, were used to produce several chrysin derivatives. These compounds were purified, characterised and tested on different cell lines and bacterial strains. From this family, 7-(2,4-dinitrophenoxy)-5-hydroxy-3-phenyl-4H-chromen-4-one (C3) was shown to be extremely active on bacterial strains methicillin-resistant Staphylococcus aureus, Pseudomonas aeruginosa and Klebsiella pneumoniae as well as having anticancer activity on a range of cancer cell lines with IC50 values less than 30 mu M. Chrysin has been known for their anticancer and antimicrobial properties, and this study not only corroborates this but also shows that it is possible to synthesise new improved derivatives with therapeutic possibilities.
引用
收藏
页码:1083 / 1092
页数:10
相关论文
共 75 条
[1]   Flavonoids as Potential anti-MRSA Agents through Modulation of PBP2a: A Computational and Experimental Study [J].
Alhadrami, Hani A. ;
Hamed, Ahmed A. ;
Hassan, Hossam M. ;
Belbahri, Lassaad ;
Rateb, Mostafa E. ;
Sayed, Ahmed M. .
ANTIBIOTICS-BASEL, 2020, 9 (09) :1-16
[2]   Dibenzoyl-methane Derivatives as a Potential and Exciting New Therapy for the Treatment of Childhood Bone Cancer [J].
Almelah, Eman ;
Smith, David P. T. ;
Mcgown, Andrew ;
Aziz, Athar ;
Potgieter, Herman J. ;
Ragazzon, Patricia .
ANTICANCER RESEARCH, 2016, 36 (11) :6043-6050
[3]   CYP1-mediated antiproliferative activity of dietary flavonoids in MDA-MB-468 breast cancer cells [J].
Androutsopoulos, Vasilis P. ;
Ruparelia, Ketan ;
Arroo, Randolph R. J. ;
Tsatsakis, Aristidis M. ;
Spandidos, Demetrios A. .
TOXICOLOGY, 2009, 264 (03) :162-170
[4]   Emergence of Klebsiella pneumoniae Carbapenemase-Producing Bacteria [J].
Arnold, Ryan S. ;
Thom, Kerri A. ;
Sharma, Saarika ;
Phillips, Michael ;
Johnson, J. Kristie ;
Morgan, Daniel J. .
SOUTHERN MEDICAL JOURNAL, 2011, 104 (01) :40-45
[5]   Antibacterial activity and proposed action mechanism of anew class of synthetic tricyclic flavonoids [J].
Babii, C. ;
Bahrin, L. G. ;
Neagu, A. -N. ;
Gostin, I. ;
Mihasan, M. ;
Birsa, L. M. ;
Stefan, M. .
JOURNAL OF APPLIED MICROBIOLOGY, 2016, 120 (03) :630-637
[6]   Synthesis and biological evaluation of novel C (7) modified chrysin analogues as antibacterial agents [J].
Babu, KS ;
Babu, TH ;
Srinivas, PV ;
Kishore, KH ;
Murthy, USN ;
Rao, JM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (01) :221-224
[7]   An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles [J].
Baumann, Marcus ;
Baxendale, Ian R. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :2265-2319
[8]   A Multinational Survey of Risk Factors for Infection with Extended-Spectrum β-Lactamase-Producing Enterobacteriaceae in Nonhospitalized Patients [J].
Ben-Ami, Ronen ;
Rodriguez-Bano, Jesus ;
Arslan, Hande ;
Pitout, Johann D. D. ;
Quentin, Claudine ;
Calbo, Esther S. ;
Azap, Oezlem K. ;
Arpin, Corinne ;
Pascual, Alvaro ;
Livermore, David M. ;
Garau, Javier ;
Carmeli, Yehuda .
CLINICAL INFECTIOUS DISEASES, 2009, 49 (05) :682-690
[9]   BDDCS, the Rule of 5 and drugability [J].
Benet, Leslie Z. ;
Hosey, Chelsea M. ;
Ursu, Oleg ;
Oprea, Tudor I. .
ADVANCED DRUG DELIVERY REVIEWS, 2016, 101 :89-98
[10]   Chrysin attenuates atopic dermatitis by suppressing inflammation of keratinocytes [J].
Choi, Jin Kyeong ;
Jang, Yong Hyun ;
Lee, Soyoung ;
Lee, Sang-Rae ;
Choi, Young-Ae ;
Jin, Meiling ;
Choi, Jung Ho ;
Park, Jee Hun ;
Park, Pil-Hoon ;
Choi, Hyukjae ;
Kwon, Taeg Kyu ;
Khang, Dongwoo ;
Kim, Sang-Hyun .
FOOD AND CHEMICAL TOXICOLOGY, 2017, 110 :142-150