Synthesis of New Cinnamoyl-Amino Acid Conjugates and in Vitro Cytotoxicity and Genotoxicity Studies.
DNA damage
amino acid
cinnamic acid
cytotoxicity
synthesis
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Aug 2022
Aug 2022
Historique:
received:
04
05
2022
accepted:
18
07
2022
pubmed:
22
7
2022
medline:
20
8
2022
entrez:
21
7
2022
Statut:
ppublish
Résumé
Amino acid conjugates are described by the reaction of amino acids with bioactive organic groups such as vitamins, hormones, flavonoids, steroids, and sugars. In this study, 12 new conjugates were synthesized by reaction of cinnamic acid derivatives with various amino acids. Cytotoxic studies against four different human cancer cells (MCF7, PC-3, Caco-2, and A2780) were carried out by MTT assay method at five different concentrations. The structure-activity relationships based on the cell viability rates were evaluated. To compare the anticancer activities of the compounds using computational chemistry methods, they were docked against A2780 human ovarian cancer, Michigan Cancer Foundation-7 (MCF7), human prostate cancer (PC-3) and human colon epidermal adenocarcinoma (Caco-2) cell lines and compared with the standard 5-Fluorouracil. The results indicate that the efficacy of cinnamic acid derivatives increases with the presence of amino acids. Comet assay was conducted to understand whether the cell deaths occur through DNA damage mechanism and the results exhibit that the changes in the specified parameters were statistically significant (p<0.05). Our study demonstrated that the compounds cause cell death through the formation of DNA damage mechanism.
Identifiants
pubmed: 35864058
doi: 10.1002/cbdv.202200426
doi:
Substances chimiques
Amino Acids
0
Antineoplastic Agents
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200426Subventions
Organisme : Inonu University Scientific Research Unit
ID : TSG-2020-2183
Organisme : Bingöl University Scientific Research Projects Coordination Unit
ID : FEF.2018.00.003
Informations de copyright
© 2022 Wiley-VHCA AG, Zurich, Switzerland.
Références
S. S. Panda, M. A. Ibrahim, H. Küçükbay, M. J. Meyers, F. M. Sverdrup, S. A. El-Feky, A. R. Katritzky, ‘Synthesis and Antimalarial Bioassay of Quinine - Peptide Conjugates’, Chem. Biol. Drug Des. 2013, 82, 361-366.
S. Sahu, S. S. Panda, A. M. Asiri, A. R. Katritzky, ‘NSAID Conjugates with Carnosine and Amino Acids’, Synthesis 2013, 45, 3369-3374.
K. Devi, P. Awasthi, ‘Sulfonamide phenylalanine (SPA) series of analogs as an antibacterial, antifungal, anticancer agents along with p53 tumor suppressor-DNA complex inhibitor - part 1’, J. Biomol. Struct. Dyn. 2020, 38, 4081-4097.
S. Celik, G. Yilmaz, A. E. Ozel, S. Akyuz, ‘Structural and spectral analysis of anticancer active cyclo(Ala-His) dipeptide’, J. Biomol. Struct. Dyn. 2022, 40, 660-672.
M. A. Ibrahim, S. S. Panda, A. S. Birs, J. C. Serrano, C. F. Gonzalez, K. A. Alamry, A. R. Katritzky, ‘Synthesis and antibacterial evaluation of amino acid-antibiotic conjugates’, Bioorg. Med. Chem. Lett. 2014, 24, 1856-1861.
S. S. Panda, R. A. Jones, C. Dennis Hall, A. R. Katritzky, ‘Applications of Chemical Ligation in Peptide Synthesis via Acyl Transfer’, Top Curr Chem. 2015, 362, 229-265.
S. S. Panda, R. N. Naumov, A. M. Asiri, A. R. Katritzky, ‘Microwave-Assisted Synthesis of Biotin Conjugates with Quinolone Antibiotics via Amino Acids’, Synthesis 2014, 46,1511-1517.
M. Ukiya, T. Kawaguchi, K. Ishii, E. Ogihara, Y. Tachi, M. Kurita, Y. Ezaki, M. Fukatsu, Y. Kushi, T. Akihisa, ‘Cytotoxic Activities of Amino Acid-Conjugate Derivatives of Abietane-Type Diterpenoids against Human Cancer Cell Lines’, Chem. Biodiversity 2013, 10, 1260-1268.
Y. Zhang, P. He, P. Zhang, X. Yi, C. Xiao, X. Chen, ‘Polypeptides-Drug Conjugates for Anticancer Therapy’, Adv. Healthcare Mater. 2021, 10, 2001974.
P. De, M. Baltas, F. Bedos-Belval, ‘Cinnamic Acid Derivatives as Anticancer Agents-A Review’, Curr. Med. Chem. 2011, 18, 1672-1703.
J. D. Guzman, P. N. Mortazavi, T. Munshi, D. Evangelopoulos, T. D. McHugh, S. Gibbons, J. Malkinson, S. Bhakta, ‘2-Hydroxy-substituted cinnamic acids and acetanilides are selective growth inhibitors of Mycobacterium tuberculosis’, MedChemComm 2014, 5, 47-50.
B. Debnath, S. Samanta, K. Roy, T. Jha, ‘QSAR Study on Some p-Arylthio Cinnamides as Antagonists of Biochemical ICAM-1/LFA-1 Interaction and ICAM-1/JY-8 Cell Adhesion in Relation to Anti-inflammatory Activity’, Bioorg. Med. Chem. 2003, 11, 1615-1619.
B. Zhang, C. Lv, W. Li, Z. Cui, D. Chen, F. Cao, F. Miao, L. Zhou, ‘Ethyl Cinnamate Derivatives as Promising High-Efficient Acaricides against Psoroptes cuniculi: Synthesis, Bioactivity and Structure-activity Relationship’, Chem. Pharm. Bull. 2015, 63, 255-262.
J. Fu, K. Cheng, Z. Zhang, R. Fang, H. Zhu, ‘Synthesis, structure and structure-activity relationship analysis of caffeic acid amides as potential antimicrobials’, Eur. J. Med. Chem. 2010, 45, 2638-2643.
J. A. Hoskins, ‘The occurrence, metabolism and toxicity of cinnamic acid and related compounds’, J. Appl. Toxicol. 1984, 4, 283-292.
H. B. Zou, S. Y. Dong, C. X. Zhou, L. H. Hu, Y. H. Wu, H. B. Li, J. X. Gong, L. L. Sun, X. M. Wu, H. Bai, B. T. Fan, X. J. Hao, J. Stöckigt, Y. Zhao, ‘Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives’, Bioorg. Med. Chem. 2006, 14, 2060-2071.
R. W. Whetten, J. J. MacKay, R. R. Sederoff, ‘Recent advances in understanding lignin biosynthesis’, Annu. Rev. Plant Physiol. Plant Mol. Biol. 1998, 49, 585-609.
W. Boerjan, J. Ralph, M. Baucher, ‘Lignin Biosynthesis’, Annu. Rev. Plant Biol. 2003, 54, 519-546.
A. Edreva, ‘The importance of non-photosynthetic pigments and cinnamic acid derivatives in photoprotection’, Agric. Ecosyst. Environ. 2005, 106, 135-146.
M. N. Clifford, ‘Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden’, J. Sci. Food Agric. 1999, 79, 362-372.
M. N. Clifford, ‘Chlorogenic acids and other cinnamates - nature, occurrence, dietary burden, absorption and metabolism’, J. Sci. Food Agric. 2000, 80, 1033-1043.
S. B. França, P. R. S. Correia, I. B. D. Castro, E. F. Silva Júnior, M. E. S. B. Barros, D. J. P. Lima, ‘Synthesis, applications and Structure-activity Relationship (SAR) of cinnamic acid derivatives: a review’, Research, Society and Development 2021, 10, e28010111691.
M. Sova, ‘Antioxidant and Antimicrobial Activities of Cinnamic Acid Derivatives’, Mini-Rev. Med. Chem. 2012, 12, 749-767.
A. K. Ghose, V. N. Viswanadhan, J. J. Wendoloski, ‘A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases’, J. Comb. Chem. 1999, 1, 55-68.
A. R. Katritzky, S. Rachwal, G. J. Hitchings, ‘Benzotriazole: A novel synthetic auxiliary’, Tetrahedron 1991, 47, 2683-2732.
A. R. Katritzky, B. V. Rogovoy, ‘Benzotriazole: An Ideal Synthetic Auxiliary’, Chem. Eur. J. 2003, 9, 4586-4593.
B. Narasimhan, D. Belsare, D. Pharande, V. Mourya, A. Dhake, ‘Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations’, Eur. J. Med. Chem. 2004, 39, 827-834.
V. T. Truong, R. R. Boyer, J. M. McKinney, S. F. O′Keefe, R. C. Williams, ‘Effect of alpha-cyclodextrin-cinnamic acid inclusion complexes on populations of Escherichia coli O157:H7 and Salmonella enterica in fruit juices’, J. Food Prot. 2010, 73, 92-6.
T. R. Burke, M. R. Fesen, A. Mazumder, J. Wang, A. M. Carothers, D. Grunberger, J. Driscoll, K. Kohn, Y. Pommier, ‘Hydroxylated aromatic inhibitors of HIV-1 integrase’, J. Med. Chem. 1995, 38, 4171-4178.
S. U. Lee, C. G. Shin, C. K. Lee, Y. S. Lee, ‘Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of L-chicoric acid, as new HIV-1 integrase inhibitors’, Eur. J. Med. Chem. 2007, 42, 1309-15.
C. Ekmekcioglu, J. Feyertag, W. Marktl, ‘Cinnamic acid inhibits proliferation and modulates brush border membrane enzyme activities in Caco-2 cells’, Cancer Lett. 1998, 128, 137-44.
L. Liu, W. R. Hudgins, S. Shack, M. Q. Yin, D. Samid, ‘Cinnamic acid: a natural product with potential use in cancer intervention’, Int. J. Cancer 1995, 62, 345-350.
E. L. Maistro, J. P. Angeli, S. F. Andrade, M. S. Mantovani, ‘In vitro genotoxicity assessment of caffeic, cinnamic and ferulic acids’, GMR Genet. Mol. Res. 2011, 10, 1130-1140.
S. Sandal, B. Yilmaz, D. O. Carpenter, ‘Genotoxic effects of PCB 52 and PCB 77 on cultured human peripheral lymphocytes’, Mutat. Res. Genet. Toxicol. Environ. Mutagen. 2008, 654, 88-92.
B. Yilmaz, S. Sandal, H. Ayvaci, N. Tug, A. Vitrinel, ‘Genotoxicity profiles in exfoliated human mammary cells recovered from lactating mothers in Istanbul; relationship with demographic and dietary factors’, Mutat. Res. Genet. Toxicol. Environ. Mutagen. 2012, 749, 17-22.
I. Beria, P. G. Baraldi, P. Cozzi, M. Caldarelli, C. Geroni, S. Marchini, N. Mongelli, R. Romagnoli, ‘Cytotoxic α-Halogenoacrylic Derivatives of Distamycin A and Congeners’, J. Med. Chem. 2004, 47, 2611-2623.
S. Sandal, B. Yilmaz, ‘Genotoxic effects of chlorpyrifos, cypermethrin, endosulfan and 2,4-D on human peripheral lymphocytes cultured from smokers and nonsmokers’, Environ. Toxicol. 2011, 26, 433-442.
S. A. Güngör, M. Tümer, M. Köse, S. Erkan, ‘N-substituted benzenesulfonamide compounds: DNA binding properties and molecular docking studies’, J. Biomol. Struct. Dyn. 2021, 1-15.
R. Huey, G. M. Morris, A. J. Olson, D. S. Goodsell, ‘A semiempirical free energy force field with charge-based desolvation’, J. Comput. Chem. 2007, 28, 1145-52.
Z. Bikadi, E. Hazai, ‘Application of the PM6 semi-empirical method to modeling proteins enhances docking accuracy of AutoDock’, J. Cheminf. 2009, 1, 115.
T. E. Messick, N. S. Russell, A. J. Iwata, K. L. Sarachan, R. Shiekhattar, J. R. Shanks, F. E. Reyes-Turcu, K. D. Wilkinson, R. Marmorstein, ‘Structural basis for ubiquitin recognition by the Otu1 ovarian tumor domain protein’, J. Biol. Chem. 2008, 283, 11038-11049.
D. Wu, Y. Li, G. Song, C. Cheng, R. Zhang, A. Joachimiak, N. Shaw, Z. J. Liu, ‘Structural basis for the inhibition of human 5,10-methenyltetrahydrofolate synthetase by N10-substituted folate analogs’, Cancer Res. 2009, 69, 7294-7301.
E. A. Stura, B. H. Muller, M. Bossus, S. Michel, C. Jolivet-Reynaud, F. Ducancel, ‘Crystal Structure of Human Prostate-Specific Antigen in a Sandwich Antibody Complex’, J. Mol. Biol. 2011, 414, 530-544.
T. L. Davis, J. R. Walker, V. Campagna-Slater, P. J. Finerty, R. Paramanathan, G. Bernstein, F. MacKenzie, W. Tempel, H. Ouyang, W. H. Lee, E. Z. Eisenmesser, S. Dhe-Paganon, ‘Structural and biochemical characterization of the human cyclophilin family of peptidyl-prolyl isomerases’, PLoS Biol. 2010, 8, e1000439.
S. Kaya, S. Erkan, D. Karakaş, ‘Computational investigation of molecular structures, spectroscopic properties and antitumor-antibacterial activities of some Schiff bases’, Spectrochim. Acta Part A 2021, 244, 118829.
E. Güzel, Ü. M. Koçyiğit, P. Taslimi, S. Erkan, O. S. Taskin, ‘Biologically active phthalocyanine metal complexes: Preparation, evaluation of α-glycosidase and anticholinesterase enzyme inhibition activities, and molecular docking studies’, J. Biochem. Mol. Toxicol. 2021, 35, e22765.
A. R. Katritzky, X. Lan, J. Z. Yang, O. V. Denisko, ‘Properties and Synthetic Utility of N-Substituted Benzotriazoles’, Chem. Rev. 1998, 98, 409-548.
K. E. Kolb, K. W. Field, P. F. Schatz, ‘A One-Step Synthesis of Cinnamic Acids Using Malonic Acid: The Verley-Doebner Modification of the Knoevenagel Condensation’, J. Chem. Educ. 1990, 67, A304.
F. Denizot, R. Lang, ‘Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability’, J. Immunol. Methods 1986, 89, 271-277.
K. Koran, Ç. Tekin, F. Biryan, S. Tekin, S. Sandal, A. O. Görgülü, ‘Synthesis, structural and thermal characterizations, dielectric properties and in vitro cytotoxic activities of new 2,2,4,4-tetra(4′-oxy-substituted-chalcone)-6,6-diphenylcyclotriphosphazene derivatives’, Med. Chem. Res. 2017, 26, 962-974.
F. Özen, S. Tekin, K. Koran, S. Sandal, A. O. Görgülü, ‘Synthesis, structural characterization, and in vitro anti-cancer activities of new phenylacrylonitrile derivatives’, Appl. Biol. Chem. 2016, 59, 239-248.
K. Koran, Ç. Tekin, E. Çalışkan, S. Tekin, S. Sandal, A. O. Görgülü, ‘Synthesis, structural and thermal characterizations and in vitro cytotoxic activities of new cyclotriphosphazene derivatives’, Phosphorus Sulfur Silicon Relat. Elem. 2017, 192, 1002-1011.
A. Karateke, N. Tuğ, D. Sahin, ‘Metastatic ovarian malignant melanoma with no obvious primary’, J. Turk. Ger. Gynecol. Assoc. 2011, 12, 181-182.
H. Mehri, B. Alizadeh, ‘Genetic-Algorithm-Based FPGA Architectural Exploration Using Analytical Models’, ACM Trans. Des. Autom. Electron. Syst. 2016, 22, 1-17.
A. Beytur, Ç. Tekin, E. Çalışkan, S. Tekin, K. Koran, A. O. Görgülü, S. Sandal, ‘Hexa-Substituted Cyclotriphosphazene Derivatives Containing Hetero-Ring Chalcones: Synthesis, in vitro Cytotoxic Activity and their DNA Damage Determination’, Bioorg. Chem. 2022, 127, 105997.