Synthesis, biological activity and preliminary in silico ADMET screening of polyamine conjugates with bicyclic systems

Molecules

Volumn 22, Issue 5, 2017, Pages

  Szumilak, Marta ^a   Galdyszynska, Malgorzata ^a   Dominska, Kamila ^a   Bak Sypien, Irena I ^a   Merecz Sadowska, Anna ^a   Stanczak, Andrzej ^a   Karwowski, Boleslaw T ^a   Piastowska Ciesielska, Agnieszka W ^a  

^a MEDICAL UNIVERSITY OF LODZ   (Poland)

Author keywords

Anticancer activity; DNA binding studies; In silico ADMET screening; Polyamine conjugates

Indexed keywords

ANTINEOPLASTIC AGENT; DNA; DNA TOPOISOMERASE; INDOLE; INDOLE DERIVATIVE; NAPHTHALENE; NAPHTHALENE DERIVATIVE; POLYAMINE; QUINAZOLINE DERIVATIVE; QUINOLINE; QUINOLINE DERIVATIVE;

ANIMAL; CELL PROLIFERATION; CELL SURVIVAL; CHEMISTRY; CONFORMATION; DRUG DESIGN; DRUG EFFECTS; ESCHERICHIA COLI; HUMAN; METABOLISM; RAT; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; DNA; DNA TOPOISOMERASES, TYPE I; DRUG DESIGN; ESCHERICHIA COLI; HUMANS; INDOLES; NAPHTHALENES; NUCLEIC ACID CONFORMATION; POLYAMINES; QUINAZOLINES; QUINOLINES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 85020188305     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules22050794     Document Type: Article

References (52)

1. Zhang, R.; Wu, X.; Yalowich, J.C.; Hasinoff, B.B. Design, synthesis, and biological evaluation of a novel series of bisintercalating DNA-binding piperazine-linked bisanthrapyrazole compounds as anticancer agents. Bioorg. Med. Chem. 2011, 19, 7023-7032. [CrossRef] [PubMed].
2. Avendano, C.; Carlos, M.J. DNA intercalators and topiosomerase inhibitors. In Medicinal Chemistry of Anticancer Drugs; Elsevier Inc.: Madrid, Spain, 2008; pp. 199-228.
3. Lorente, A.; Vázquez, Y.; Fernández, M.J.; Ferrández, A. Bisacridines with aromatic linking chains. Synthesis, DNA interaction, and antitumor activity. Bioorg. Med. Chem. 2004, 12, 4307-4312. [CrossRef] [PubMed].
4. Rescifina, A.; Zagni, C.; Varrica, M.G.; Pistara, V.; Corsaro, A. Recent advances in small organic molecules as DNA intercalating agents: Synthesis, activity, and modeling. Eur. J. Med. Chem. 2014, 74, 95-115. [CrossRef] [PubMed].
5. Brana, M.F.; Cacho, M.; Gradillas, A.; de Pascual-Teresa, B.; Ramos, A. Intercalators as anticancer drugs. Curr. Pharm. Des. 2001, 7, 1745-1780. [CrossRef] [PubMed].
6. Rong, R.X.; Sun, Q.; Ma, C.L.; Chen, B.; Wang, W.Y.; Wang, Z.A.; Wang, K.R.; Cao, Z.R.; Li, X.L. Development of novel bis-naphthalimide derivatives and their anticancer properties. Med. Chem. Commun. 2016, 7, 679-685. [CrossRef].
7. Bestwick, C.S.; Ralton, L.D.; Milne, L.; Kong Thoo Lin, P.; Duthie, S.J. The influence of bisnaphthalimidopropyl polyamines on DNA instability and repair in Caco-2 colon epithelial cells. Cell Biol. Toxicol. 2011, 27, 455-463. [CrossRef] [PubMed].
8. Brana, M.F.; Cacho, M.; Ramos, A.; Dominguez, M.T.; Pozuelo, J.M.; Abradelo, C.; Rey-Stolle, M.F.; Yuste, M.; Carrasco, C.; Bailly, C. Synthesis, biological evaluation and DNA binding properties of novel mono and bisnaphthalimides. Org. Biomol. Chem. 2003, 1, 648-654. [CrossRef] [PubMed].
9. Gamage, S.A.; Spicer, J.A.; Atwell, G.J.; Finlay, G.J.; Baguley, B.C.; Denny, W.A. Structure-Activity relationships for substituted bis(acridine-4-carboxamides): A new class of anticancer agents. J. Med. Chem. 1999, 42, 2383-2393. [CrossRef] [PubMed].
10. Demeunynck, M.; Charmantray, F.; Martelli, A. Interest of acridine derivatives in the anticancer chemotherapy. Curr. Pharm. Des. 2001, 7, 1703-1724. [CrossRef] [PubMed].
11. Antonini, I. Intriguing classes of acridine derivatives as DNA-binding antitumour agents: From pyrimido[5, 6, 1- de]acridines to bis(acridine-4-carboxamides). Med. Chem. Rev. Online 2004, 1, 267-290. [CrossRef].
12. Spicer, J.A.; Gamage, S.A.; Finlay, G.J.; Baguley, B.C.; Denny, W.A. Dimeric analogues of non-cationic tricyclic aromatic carboxamides are a new class of cytotoxic agents. Anti-Cancer Drug Des. 1999, 14, 281-289.
13. Spicer, J.A.; Gamage, S.A.; Rewcastle, G.W.; Finlay, G.J.; Bridewell, D.J.A.; Baguley, B.C.; Denny, W.A. Bis(phenazine-1-carboxamides): Structure-Activity relationships for a new class of dual topoisomerase I/II-directed anticancer drugs. J. Med. Chem. 2000, 43, 1350-1358. [CrossRef] [PubMed].
14. Gamage, S.A.; Spicer, J.A.; Finlay, G.J.; Stewart, A.J.; Charlton, P.; Baguley, B.C.; Denny, W.A. Dicationic bis(9-methylphenazine-1-carboxamides): Relationships between biological activity and linker chain structure for a series of potent topoisomerase targeted anticancer drugs. J. Med. Chem. 2001, 44, 1407-1415. [CrossRef] [PubMed].
15. Lin, C.; Yang, D. DNA recognition by a novel bis-intercalator, potent anticancer drug XR5944. Curr. Top. Med. Chem. 2015, 15, 1385-1397. [CrossRef] [PubMed].
16. Zhang, G.S.; Fang, L.Y.; Zhu, L.Z.; Sun, D.X.;Wang, P.G. Syntheses and biological activity of bisdaunorubicins. Bioorg. Med. Chem. 2006, 14, 426-434. [CrossRef] [PubMed].
17. Chaires, J.B.; Leng, F.F.; Przewloka, T.; Fokt, I.; Ling, Y.H.; Perez-Soler, R.; Priebe, W. Structure-based design fill of a new bisintercalating anthracycline antibiotic. J. Med. Chem. 1997, 40, 261-266. [CrossRef] [PubMed].
18. Mansilla, S.; Vizcaino, C.; Rodriguez-Sanchez, M.A.; Priebe, W.; Portugal, J. Autophagy modulates the effects of bis-Anthracycline WP631 on p53-deficient prostate cancer cells. J. Cell. Mol. Med. 2015, 19, 786-798. [CrossRef] [PubMed].
19. Fernandez, J.; Marin, L.; Alvarez-Alonso, R.; Redondo, S.; Carvajal, J.; Villamizar, G.; Villar, C.J.; Lombo, F. Biosynthetic modularity rules in the bisintercalator family of antitumor compounds. Mar. Drugs 2014, 12, 2668-2699. [CrossRef] [PubMed].
20. Burns, M.R.; LaTurner, S.; Ziemer, J.; McVean, M.; Devens, B.; Carlson, C.L.; Graminski, G.F.; Vanderwerf, S.M.; Weeks, R.S.; Carreon, J. Induction of apoptosis by aryl-substituted diamines: Role of aromatic group substituents and distance between nitrogens. Bioorg. Med. Chem. Lett. 2002, 12, 1263-1267. [CrossRef].
21. Cain, B.F.; Baguley, B.C.; Denny, W.A. Potential antitumor agents. 28. Deoxyribonucleic-Acid polyintercalating agents. J. Med. Chem. 1978, 21, 658-668. [CrossRef] [PubMed].
22. Sartorius, J.; Schneider, H.J. Intercalation mechanisms with ds-DNA: Binding modes and energy contributions with benzene, naphthalene, quinoline and indole derivatives including some antimalarials. J. Chem. Soc. Perkin Trans. 2 1997, 2319-2327. [CrossRef].
23. Szumilak, M.; Szulawska-Mroczek, A.; Koprowska, K.; Stasiak, M.; Lewgowd, W.; Stanczak, A.; Czyz, M. Synthesis and in vitro biological evaluation of new polyamine conjugates as potential anticancer drugs. Eur. J. Med. Chem. 2010, 45, 5744-5751. [CrossRef] [PubMed].
24. Szulawska-Mroczek, A.; Szumilak, M.; Szczesio, M.; Olczak, A.; Nazarski, R.B.; Lewgowd, W.; Czyz, M.; Stanczak, A. Synthesis and biological evaluation of new bischromone derivatives with antiproliferative activity. Arch. Pharm. 2013, 346, 34-43. [CrossRef] [PubMed].
25. Szumilak, M.; Galdyszynska, M.; Dominska, K.; Stanczak, A.; Piastowska-Ciesielska, A. Antitumor activity of polyamine conjugates in human prostate and breast cancer. Acta Biochim. Pol. 2017, 64. [CrossRef].
26. Szumilak, M.; Merecz, A.; Strek, M.; Stanczak, A.; Inglot, T.W.; Karwowski, B.T. DNA interaction studies of selected polyamine conjugates. Int. J. Mol. Sci. 2016, 17, 1560. [CrossRef] [PubMed].
27. Thompson, T.N. Optimization of metabolic stability as a goal of modern drug design. Med. Res. Rev. 2001, 21, 412-449. [CrossRef] [PubMed].
28. Errede, L.A.; Oien, H.T.; Yarian, D.R. Acylanthranils 3. Influence of ring substituents on reactivity and selectivity in reaction of acylanthranils with amines. J. Org. Chem. 1977, 42, 12-18. [CrossRef].
29. Staab, H.A. Synthesen Mit Heterocyclishen Amiden (Azoliden). Angew. Chem. 1962, 74, 407-423. [CrossRef].
30. Errede, L.A. Acylanthranils 1 The pathway of quinazolone formation in the reaction of acylanthranils with anilines. J. Org. Chem. 1976, 41, 1763-1765. [CrossRef].
31. Errede, L.A.; McBrady, J.J.; Oien, H.T. Acylanthranils. 2. The problem of selectivity in the reaction of acetylanthranil with anilines. J. Org. Chem. 1976, 41, 1765-1768. [CrossRef].
32. Stanczak, A.; Lewgowd, W.; Ochocki, Z.; Pakulska, W.; Szadowska, A. Synthesis, structures and biological activity of some 4-Amino-3-cinnoline-carboxylic acid derivatives-Part 2. Pharmazie 1997, 52, 91-97. [PubMed].
33. Clark, J.; Hitiris, G. Heterocyclic studies 43. Thieno[2, 3-d:4, 5-d0]dipyrimidines. J. Chem. Soc. Perkin Trans. 1 1984, 9, 2005-2008. [CrossRef].
34. Gravier, D.; Dupin, J.P.; Casadebaig, F.; Hou, G.; Boisseau, M.; Bernard, H. Synthesis and in vitro study of platelet antiaggregant activity of some 4-quinazolinone derivatives. Pharmazie 1992, 47, 91-94. [PubMed].
35. Malamas, M.S.; Millen, J. Quinazolineacetic acids and related analogs as aldose reductase inhibitors. J. Med. Chem. 1991, 34, 1492-1503. [CrossRef] [PubMed].
36. Stanczak, A.; Lewgowd, W.; Pakulska, W. Synthesis and biological activity of some 4-Amino-3-cinnoline carboxylic acid derivatives-Part 4: 2, 4-dioxo-1, 2, 3, 4-Tetrahydropyrimido[5, 4-c] cinnolines. Pharmazie 1998, 53, 156-161. [CrossRef] [PubMed].
37. Piastowska-Ciesielska, A.W.; Kozlowski, M.; Wagner, W.; Dominska, K.; Ochedalski, T. Effect of an angiotensin II type 1 receptor blocker on caveolin-1 expression in prostate cancer cells. Arch. Med. Sci. 2013, 9, 739-744. [CrossRef] [PubMed].
38. Guedin, A.; Lacroix, L.; Mergny, J.-L. Thermal Melting Studies of Ligand DNA Interactions. In Drug-DNA Interaction Protocols; Fox, K.R., Ed.; Humana Press: New York, NY, USA, 2010; pp. 25-35. [CrossRef].
39. Palchaudhuri, R.; Hergenrother, P.J. DNA as a target for anticancer compounds: Methods to determine the mode of binding and the mechanism of action. Curr. Opin. Biotechnol. 2007, 18, 497-503. [CrossRef] [PubMed].
40. Jianling, W.; Urban, L. The impact of early ADME profiling on drug discovery and development strategy. Drug Discov. World 2004, 4, 73-86.
41. ACD/Percepta, Version 14.0.0 (Build 2726); Advanced Chemistry Development Inc.: Toronto, ON, Canada, 2015; Available online: Www.acdlabs.com (accessed on 16 January 2017).
42. Lipinski, C.A.; Lombardo, F.; Dominy, B.W.; Feeney, P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 1997, 23, 3-25. [CrossRef].
43. Lanevskij, K.; Japertas, P.; Didziapetris, R.; Petrauskas, A. Ionization-specific prediction of blood-brain permeability. J. Pharm. Sci. 2009, 98, 122-134. [CrossRef] [PubMed].
44. Moroy, G.; Martiny, V.Y.; Vayer, P.; Villoutreix, B.O.; Miteva, M.A. Toward in silico structure-based ADMET prediction in drug discovery. Drug Discov. Today 2012, 17, 44-55. [CrossRef] [PubMed].
45. Kleandrova, V.V.; Luan, F.; Speck-Planche, A.; Cordeiro, M.N. In silico assessment of the acute toxicity of chemicals: Recent advances and new model for multitasking prediction of toxic effect. Mini Rev. Med. Chem. 2015, 15, 677-686. [CrossRef] [PubMed].
46. The European Parliament and the Council of the European Union. Regulation (EC) No 1272/2008 of the European Parliament and of The Council of 16 December 2008 on Classification, Labelling and Packaging of Substances and Mixtures, Amending and Repealing Directives 67/548/EEC and 1999/45/EC, and Amending Regulation (EC) No 1907/2006. 2006.
47. Saleh, A.M.; Aljada, A.; El-Abadelah, M.M.; Sabri, S.S.; Zahra, J.A.; Nasr, A.; Aziz, M.A. The pyridone-Annelated isoindigo (50-Cl) induces apoptosis, dysregulation of mitochondria and formation of ROS in leukemic HL-60 cells. Cell. Physiol. Biochem. 2015, 35, 1958-1974. [CrossRef] [PubMed].
48. Tsakalozou, E.; Adane, E.D.; Kuo, K.L.; Daily, A.; Moscow, J.A.; Leggas, M. The effect of breast cancer resistance protein, multidrug resistant protein 1, and organic anion-Transporting polypeptide 1B3 on the antitumor efficacy of the lipophilic camptothecin 7-T-butyldimethylsilyl-10-hydroxycamptothecin (AR-67) in vitro. Drug Metab. Dispos. 2013, 41, 1404-1413. [CrossRef] [PubMed].
49. Sappal, D.S.; McClendon, A.K.; Fleming, J.A.; Thoroddsen, V.; Connolly, K.; Reimer, C.; Blackman, R.K.; Bulawa, C.E.; Osheroff, N.; Charlton, P.; et al. Biological characterization of MLN944: A potent DNA binding agent. Mol. Cancer Ther. 2004, 3, 47-58. [PubMed].
50. Reynolds, D.P.; Lanevskij, K.; Japertas, P.; Didziapetris, R.; Petrauskas, A. Ionization-specific analysis of human intestinal absorption. J. Pharm. Sci. 2009, 98, 4039-4054. [CrossRef] [PubMed].
51. Sazonovas, A.; Japertas, P.; Didziapetris, R. Estimation of reliability of predictions and model applicability domain evaluation in the analysis of acute toxicity (LD50). SAR QSAR Environ. Res. 2010, 21, 127-148. [CrossRef] [PubMed].
52. Kang, J.-A.; Yang, Z.; Lee, J.Y.; De, U.; Kim, T.H.; Park, J.Y.; Lee, H.J.; Park, Y.J.; Chun, P.; Kim, H.S.; Jeong, L.S.; Moona, H.R. Design, synthesis and anticancer activity of novel dihydrobenzofuro[4, 5-b] [1, 8]naphthyridin-6-one derivatives. Bioorg. Med. Chem. 2011, 21, 5730-5734. [CrossRef] [PubMed].