The synthesis and the in vitro cytotoxicity studies of bisnaphthalimidopropyl polyamine derivatives against colon cancer cells and parasite Leishmania infantum

• Published in: Bioorganic & medicinal chemistry Vol. 15; no. 1; pp. 541 - 545
• Main Authors: Oliveira, João, Ralton, Lynda, Tavares, Joana, Codeiro-da-Silva, Anabela, Bestwick, Charles S., McPherson, Anne, Thoo Lin, Paul Kong
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 2007
• Subjects: Animals; Anticancer; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Antiparasitic activity; Antiparasitic Agents - chemical synthesis; Antiparasitic Agents - chemistry; Antiparasitic Agents - pharmacology; Bisnaphthalimidopropyl; Caco-2 Cells; Cell Proliferation - drug effects; Colonic Neoplasms - drug therapy; Drug Screening Assays, Antitumor; Humans; Leishmania infantum; Leishmania infantum - drug effects; Molecular Structure; Parasitic Sensitivity Tests; Polyamines; Polyamines - chemical synthesis; Polyamines - chemistry; Polyamines - pharmacology; Stereoisomerism; Structure-Activity Relationship; Antiparasitic activity; BNIPDpta; BNIPDadec; BNIPDaoct; BNIPSpd; BNIPDanon; BNIPDeta; MTT; Polyamines; Bisnaphthalimidopropyl; THF; DMF; Anticancer
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2006.09.031

Bisnaphthalimidopropyl derivatives (BNIPSpd, BNIPDaoct, BNIPDanon, BNIPDadec, BNIPDpta and BNIPDeta) were synthesised in yields ranging from 50% to 70% and their cytotoxicity against colon cancer cells (Caco-2) and the parasite Leishmania infantum determined using the MTT assay. Cytotoxicity within Caco-2 cells was manifested with IC 50 values between 0.3 and 22 μM. Compounds with the central longer alkyl chains exhibited the highest cytotoxicity. Against L. infantum, IC 50 values were encompassed within a narrower concentration range of 0.47–1.54 μM. In the parasites, the presence of nitrogen in the central chain and the length of the central alkyl chains did not especially enhance cytotoxicity. This may be due to the way these compounds are transported in the cells.