BCESA: a nano-scaled intercalator capable of targeting tumor tissue and releasing anti-tumoral β-carboline-3-carboxylic acid

References

• Shankaraiah N, Jadala C, Nekkanti S, et al. Design and synthesis of C3-tethered 1,2,3-triazolo-beta-carboline derivatives: anticancer activity, DNA-binding ability, viscosity and molecular modeling studies. Bioorg Chem. 2016;64:42–50. doi:10.1016/j.bioorg.2015.11.00526657602
   PubMed Web of Science ®Google Scholar
• Ling Y, Guo J, Yang Q, et al. Development of novel beta-carboline-based hydroxamate derivatives as HDAC inhibitors with antiproliferative and antimetastatic activities in human cancer cells. Eur J Med Chem. 2018;144:398–409. doi:10.1016/j.ejmech.2017.12.06129288941
   PubMedGoogle Scholar
• Fiore M, Forli S, Manetti F. Targeting Mitogen-Activated Protein Kinase-Activated Protein Kinase 2 (MAPKAPK2, MK2): medicinal chemistry efforts to lead small molecule inhibitors to clinical trials. J Med Chem. 2016;59(8):3609–3634. doi:10.1021/acs.jmedchem.5b0145726502061
   PubMed Web of Science ®Google Scholar
• Suh YG, Lim C, Sim J, Lee JK, Surh YJ, Paek SM. Construction of the azacyclic core of tabernaemontanine-related alkaloids via tandem Reformatsky-Aza-Claisen rearrangement. J Org Chem. 2017;82(3):1464–1470. doi:10.1021/acs.joc.6b0264828051867
   PubMedGoogle Scholar
• Kovvuri J, Nagaraju B, Nayak VL, et al. Design, synthesis and biological evaluation of new beta-carboline-bisindole compounds as DNA binding, photocleavage agents and topoisomerase I inhibitors. Eur J Med Chem. 2018;143:1563–1577. doi:10.1016/j.ejmech.2017.10.05429129513
   PubMed Web of Science ®Google Scholar
• Zheng C, Fang Y, Tong W, et al. Synthesis and biological evaluation of novel tetrahydro-beta-carboline derivatives as antitumor growth and metastasis agents through inhibiting the transforming growth factor-beta signaling pathway. J Med Chem. 2014;57(3):600–612. doi:10.1021/jm401117t24417479
   PubMedGoogle Scholar
• Shankaraiah N, Nekkanti S, Chudasama KJ, et al. Design, synthesis and anticancer evaluation of tetrahydro-beta-carboline-hydantoin hybrids. Bioorg Med Chem Lett. 2014;24(23):5413–5417. doi:10.1016/j.bmcl.2014.10.03825453799
   PubMed Web of Science ®Google Scholar
• Ling Y, Xu C, Luo L, et al. Novel beta-carboline/hydroxamic acid hybrids targeting both histone deacetylase and DNA display high anticancer activity via regulation of the p53 signaling pathway. J Med Chem. 2015;58(23):9214–9227. doi:10.1021/acs.jmedchem.5b0105226555243
   PubMedGoogle Scholar
• Dighe SU, Khan S, Soni I, et al. Synthesis of beta-carboline-based N-heterocyclic carbenes and their antiproliferative and antimetastatic activities against human breast cancer cells. J Med Chem. 2015;58(8):3485–3499. doi:10.1021/acs.jmedchem.5b0001625835200
   PubMedGoogle Scholar
• Frederick R, Bruyere C, Vancraeynest C, et al. Novel trisubstituted harmine derivatives with original in vitro anticancer activity. J Med Chem. 2012;55(14):6489–6501. doi:10.1021/jm300542e22770529
   PubMed Web of Science ®Google Scholar
• Dai J, Dan W, Schneider U, Wang J. β-Carboline alkaloid monomers and dimers: occurrence, structural diversity, and biological activities. Eur J Med Chem. 2018;157:622–656. doi:10.1016/j.ejmech.2018.08.02730125723
   PubMed Web of Science ®Google Scholar
• Yang F, Zhang T, Wu H, et al. Design and optimization of novel hydroxamate-based histone deacetylase inhibitors of Bis-substituted aromatic amides bearing potent activities against tumor growth and metastasis. J Med Chem. 2014;57(22):9357–9369. doi:10.1021/jm501214825360834
   PubMedGoogle Scholar
• Behforouz M, Cai W, Stocksdale MG, et al. Novel lavendamycin analogues as potent HIV-reverse transcriptase inhibitors: synthesis and evaluation of anti-reverse transcriptase activity of amide and ester analogues of lavendamycin. J Med Chem. 2003;46(26):5773–5780. doi:10.1021/jm030441414667230
   PubMedGoogle Scholar
• Sathish M, Chetan Dushantrao S, Nekkanti S, et al. Synthesis of DNA interactive C3-trans-cinnamide linked beta-carboline conjugates as potential cytotoxic and DNA topoisomerase I inhibitors. Bioorg Med Chem. 2018;26(17):4916–4929. doi:10.1016/j.bmc.2018.08.03130172625
   PubMedGoogle Scholar
• Chen J, Peng F, Zhang Y, et al. Synthesis, characterization, cellular uptake and apoptosis-inducing properties of two highly cytotoxic cyclometalated ruthenium(II) β-carboline complexes. Eur J Med Chem. 2017;140:104–117. doi:10.1016/j.ejmech.2017.09.00728923379
   PubMed Web of Science ®Google Scholar
• Carvalho A, Chu J, Meinguet C, et al. A harmine-derived beta-carboline displays anti-cancer effects in vitro by targeting protein synthesis. Eur J Pharmacol. 2017;805:25–35. doi:10.1016/j.ejphar.2017.03.03428322844
   PubMed Web of Science ®Google Scholar
• Atteya R, Ashour ME, Ibrahim EE, Farag MA, El-Khamisy SF. Chemical screening identifies the beta-Carboline alkaloid harmine to be synergistically lethal with doxorubicin. Mech Ageing Dev. 2017;161(Pt A):141–148. doi:10.1016/j.mad.2016.04.01227282658
   PubMedGoogle Scholar
• Samundeeswari S, Chougala B, Holiyachi M, et al. Design and synthesis of novel phenyl −1, 4-beta-carboline-hybrid molecules as potential anticancer agents. Eur J Med Chem. 2017;128:123–139. doi:10.1016/j.ejmech.2017.01.01428171832
   PubMedGoogle Scholar
• Bai B, Li XY, Liu L, Li Y, Zhu HJ. Syntheses of novel beta-carboline derivatives and the activities against five tumor-cell lines. Bioorg Med Chem Lett. 2014;24(1):96–98. doi:10.1016/j.bmcl.2013.11.07624345445
   PubMedGoogle Scholar
• Liew LPP, Fleming JM, Longeon A, et al. Synthesis of 1-indolyl substituted β-carboline natural products and discovery of antimalarial and cytotoxic activities. Tetrahedron. 2014;70(33):4910–4920. doi:10.1016/j.tet.2014.05.068
   Web of Science ®Google Scholar
• Wu JH, Li CY, Zhao M, Wang WJ, Wang YJ, Peng SQ. A class of novel carboline intercalators: their synthesis, in vitro anti-proliferation, in vivo anti-tumor action, and 3D QSAR analysis. Bioorg Med Chem. 2010;18(17):6220–6229. doi:10.1016/j.bmc.2010.07.04320692841
   PubMedGoogle Scholar
• Wu JH, Zhao M, Qian KD, Lee KH, Morris-Natschke S, Peng SQ. Novel N-(3-carboxyl-9-benzyl-beta-carboline-1-yl)ethylamino acids: synthesis, anti-tumor evaluation, intercalating determination, 3D QSAR analysis and docking investigation. Eur J Med Chem. 2009;44(10):4153–4161. doi:10.1016/j.ejmech.2009.05.00619535177
   PubMedGoogle Scholar
• Wu JH, Wei L, Zhao M, Wang YJ, Kang GF, Peng SQ. N-[2(3-Carboxyl-9-benzyl-carboline-1-yl)ethyl-1-yl]-amino acids: correlation of spectral property with in vivo anti-tumor activity. Med Chem Res. 2012;21(1):116–123. doi:10.1007/s00044-010-9504-1
   Web of Science ®Google Scholar
• Serfilippi LM, Pallman DR, Russell B. Serum clinical chemistry and hematology reference values in outbred stocks of albino mice from three commonly used vendors and two inbred strains of albino mice. Contemp Top Lab Anim Sci. 2003;42(3):46–52.
   PubMedGoogle Scholar
• Zhang XY, Yang YF, Zhao M, et al. A class of Trp-Trp-AA-OBzl: synthesis, in vitro anti-proliferation/in vivo anti-tumor evaluation, intercalation-mechanism investigation and 3D QSAR analysis. Eur J Med Chem. 2011;46(8):3410–3419. doi:10.1016/j.ejmech.2011.05.00421620529
   PubMedGoogle Scholar
• Feng Q, Zhao M, Gan T, et al. DHDMIQK(KAP): a novel nano-delivery system of dihydroxyl-tetrahydro-isoquinoline-3-carboxylic acid and KPAK towards the thrombus. J Mater Chem B. 2016;4(36):5991–6003. doi:10.1039/C6TB00874G
   PubMed Web of Science ®Google Scholar
• Wu J, Zhu H, Zhao M, et al. IQCA-TASS: a nano-scaled P-selectin inhibitor capable of targeting thrombus and releasing IQCA/TARGD(S)S in vivo. J Mater Chem B. 2017;5(5):877–1120.
   Web of Science ®Google Scholar
• Wu J, Zhao M, Wang Y, et al. N-(3-hydroxymethyl-β-carboline-1-yl-ethyl-2-yl)-L-Phe: development toward a nanoscaled antitumor drug capable of treating complicated thrombosis and inflammation. Drug Des Devel Ther. 2017;11:225–239. doi:10.2147/DDDT.S123919
   PubMed Web of Science ®Google Scholar
• Zhu H, Song Y, Wang Y, et al. Design, synthesis and evaluation of a novel π–π stacking nano-intercalator as an anti-tumor agent. Med Chem Commun. 2016;7(2):247–257. doi:10.1039/C5MD00507H
   Google Scholar
• Wu J, Zhu H, Yang G, et al. Design and synthesis of nanoscaled IQCA-TAVV as a delivery system capable of antiplatelet activation, targeting arterial thrombus and releasing IQCA. Int J Nanomedicine. 2018;13:1139–1158. doi:10.2147/IJN.S15020529520141
   PubMed Web of Science ®Google Scholar
• Xu X, Wang Y, Wu J, et al. ATIQCTPC: a nanomedicine capable of targeting tumor and blocking thrombosis in vivo. Int J Nanomedicine. 2017;12:4415–4431. doi:10.2147/IJN.S12998928652742
   PubMedGoogle Scholar
• Jin SM, Wang YN, Zhu HM, et al. Nanosized aspirin-Arg-Gly-Asp-Val: delivery of aspirin to thrombus by the target carrier Arg-Gly-Asp-Val tetrapeptide. ACS Nano. 2013;7(9):7664–7673. doi:10.1021/nn402171v23931063
   PubMed Web of Science ®Google Scholar
• Hu X, Zhao M, Wang Y, et al. Tetrahydro-β-carboline-3-carboxyl-thymopentin: a nano-conjugate for releasing pharmacophores to treat tumor and complications. J Mater Chem B. 2016;4:1384–1397. doi:10.1039/C5TB01930C
   PubMed Web of Science ®Google Scholar
• Xu W, Zhao M, Wang Y, et al. Design, synthesis, and in vivo evaluations of benzyl Nω-nitro-Nα-(9H-pyrido[3,4-b]indole-3-carbonyl)-l-argininate as an apoptosis inducer capable of decreasing the serum concentration of P-selectin. Med Chem Commun. 2016;7(9):1730–1737. doi:10.1039/C6MD00215C
   Web of Science ®Google Scholar
• Ma H, Zhao M, Wang Y, et al. Cholyl-l-lysine-carboxylbutyryl adriamycin prodrugs targeting chemically induced liver injury. J Mater Chem B. 2017;5(3):470–478. doi:10.1039/C6TB02205G
   PubMed Web of Science ®Google Scholar
• Jiang X, Zhao M, Wang Y, et al. RGD(F/S/V)-Dex: towards the development of novel, effective, and safe glucocorticoids. Drug Des Devel Ther. 2016;10:1059–1076. doi:10.2147/DDDT.S99568
   PubMed Web of Science ®Google Scholar
• Wu JH, Wang YJ, Wang YN, et al. Cu2+-RGDFRGDS: exploring the mechanism and high efficacy of the nanoparticle in antithrombotic therapy. Int J Nanomedicine. 2015;10:2925–2938. doi:10.2147/IJN.S7669125931819
   PubMed Web of Science ®Google Scholar
• Fujita Y, Mie M, Kobatake E. Construction of nanoscale protein particle using temperature-sensitive elastin-like peptide and polyaspartic acid chain. Biomaterials. 2009;30(20):3450–3457. doi:10.1016/j.biomaterials.2009.03.01219324406
   PubMedGoogle Scholar
• Chen YF, Lin YC, Chen JP, et al. Synthesis and biological evaluation of novel 3,9-substituted beta-carboline derivatives as anticancer agents. Bioorg Med Chem Lett. 2015;25(18):3873–3877. doi:10.1016/j.bmcl.2015.07.05826235951
   PubMedGoogle Scholar
• Zhao M, Bi L, Wang W, et al. Synthesis and cytotoxic activities of beta-carboline amino acid ester conjugates. Bioorg Med Chem. 2006;14(20):6998–7010. doi:10.1016/j.bmc.2006.06.02116806943
   PubMedGoogle Scholar