title: Improved anticancer and antiparasitic activity of new lawsone Mannich bases.
abstract: Substituted lawsone Mannich bases 2a-e, 3a-e and 4a-e were prepared and tested for their biological activities. The new fatty alkyl substituted compounds 2a-c exhibited strong and selective growth inhibitory activities in the low one-digit micromolar and sub-micromolar range against a panel of human cancer cell lines associated with ROS formation. In addition, compounds 2a-c revealed sub-micromolar anti-trypanosomal activities against parasitic Trypanosoma brucei brucei cells via deformation of the microtubule cytoskeleton. The N-hexadecyl compound 2c was also highly active against locally isolated Entamoeba histolytica parasite samples exceeding the activity of metronidazole.
authors.affiliation: Organic Chemistry Laboratory, University of Bayreuth, Universitaetsstrasse 30, 95440 Bayreuth, Germany.
authors.forename: Katharina
authors.initials: K
authors.lastname: Mahal
authors.affiliation: Karmanos Cancer Institute, Dept. of Pathology, Wayne State University, Detroit 48201, USA.
authors.forename: Aamir
authors.initials: A
authors.lastname: Ahmad
authors.affiliation: Organic Chemistry Laboratory, University of Bayreuth, Universitaetsstrasse 30, 95440 Bayreuth, Germany.
authors.forename: Florian
authors.initials: F
authors.lastname: Schmitt
authors.affiliation: Laboratory of Molecular Parasitology, Department of Genetics, University of Bayreuth, 95440 Bayreuth, Germany.
authors.forename: Julia
authors.initials: J
authors.lastname: Lockhauserbäumer
authors.affiliation: Laboratory of Molecular Parasitology, Department of Genetics, University of Bayreuth, 95440 Bayreuth, Germany.
authors.forename: Kathrin
authors.initials: K
authors.lastname: Starz
authors.affiliation: Department of Chemistry, Abeda Inamdar Senior College, Pune 411001, India.
authors.forename: Rohan
authors.initials: R
authors.lastname: Pradhan
authors.affiliation: Department of Chemistry, Abeda Inamdar Senior College, Pune 411001, India.
authors.forename: Subhash
authors.initials: S
authors.lastname: Padhye
authors.affiliation: Karmanos Cancer Institute, Dept. of Pathology, Wayne State University, Detroit 48201, USA.
authors.forename: Fazlul H
authors.initials: FH
authors.lastname: Sarkar
authors.affiliation: Department of Microbiology and Parasitology, Medicinal and Aromatic Plants Research Institute, National Centre for Research, Khartoum, Sudan; College of Science and Arts (Ar Rass), Qassim University, Buraidah, Saudi Arabia.
authors.forename: Waleed S
authors.initials: WS
authors.lastname: Koko
authors.affiliation: Organic Chemistry Laboratory, University of Bayreuth, Universitaetsstrasse 30, 95440 Bayreuth, Germany.
authors.forename: Rainer
authors.initials: R
authors.lastname: Schobert
authors.affiliation: Laboratory of Molecular Parasitology, Department of Genetics, University of Bayreuth, 95440 Bayreuth, Germany.
authors.forename: Klaus
authors.initials: K
authors.lastname: Ersfeld
authors.affiliation: Organic Chemistry Laboratory, University of Bayreuth, Universitaetsstrasse 30, 95440 Bayreuth, Germany. Electronic address: bernhard.biersack@yahoo.com.
authors.forename: Bernhard
authors.initials: B
authors.lastname: Biersack
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D003599:Cytoskeleton / Q000187:drug effects / Q000378:metabolism; D015195:Drug Design; D004748:Entamoeba histolytica / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D008352:Mannich Bases / Q000737:chemistry*; D009285:Naphthoquinones / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014344:Trypanocidal Agents / Q000737:chemistry* / Q000494:pharmacology*; D014346:Trypanosoma brucei brucei / Q000187:drug effects
chemical_list: D000970:Antineoplastic Agents; D008352:Mannich Bases; D009285:Naphthoquinones; D014344:Trypanocidal Agents; C005090:lawsone
keywords: Anticancer drugs; Antiparasitic drugs; Lawsone; Mannich base