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

Oliveira, João Filipe; Ralton, Lynda D.; Tavares, Joana; Codeiro-da-Silva, Anabela; Bestwick, Charles; McPherson, Anne; Lin, Paul Kong Thoo

doi:10.1016/j.bmc.2006.09.031

Cited by 28 publications

(50 citation statements)

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“…However, a great deal of inter-and intra-subject variation is experienced, perhaps due to erratic and incomplete absorption of the drug from the GI tract [40]. The novel anticancer drug bisnaphthalimidopropyldiaminooctane (BNIPDaoct) has been reported to possess great potential as a cytotoxic agent in pancreatic cancer treatment [41,42]. BNIPDaoct has shown negligible aqueous solubility and as a result toxic solvents such as dimethyl sulfoxide (DMSO) have been required in order to dissolve the drug [41,43].…”

Section: Introductionmentioning

confidence: 99%

“…The novel anticancer drug bisnaphthalimidopropyldiaminooctane (BNIPDaoct) has been reported to possess great potential as a cytotoxic agent in pancreatic cancer treatment [41,42]. BNIPDaoct has shown negligible aqueous solubility and as a result toxic solvents such as dimethyl sulfoxide (DMSO) have been required in order to dissolve the drug [41,43]. Here, we will investigate the potential of the two PAA derivatives in BNIPDaoct solubilisation using the optimal formulation strategies determined.…”

Section: Introductionmentioning

confidence: 99%

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Poly(allylamine) Magnetomicelles for Image Guided Drug Delivery

Barnett¹,

Lees²,

Curtis³

et al. 2013

PNT

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Poly(allylamine) Magnetomicelles for Image Guided Drug Delivery

Barnett¹,

Lees²,

Curtis³

et al. 2013

PNT

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“…In the past decade, a series of bisnaphthalimide polyamine derivatives were synthesized and evaluated in vitro (9,10,13,14). However, mononaphthalimide polyamine conjugates were seldom reported compared to their bisnaphthalimide counterparts.…”

Section: Introductionmentioning

confidence: 99%

Reactive oxygen species (ROS) accumulation induced by mononaphthalimide-spermidine leads to intrinsic and AIF-mediated apoptosis in HeLa cells

Zhao

2011

Oncol Rep

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Abstract. Developing polyamine conjugates having the potential of transporting naphthalimide selectively into tumor cells is attractive. However, the evaluation of their cytotoxic mechanism has not been comprehensive. This study focused on the effects of mononaphthalimide spermidine (MNISpd) conjugate on apoptosis induction and the relationship between MNISpd-induced apoptosis and reactive oxygen species (ROS) in HeLa cells. Our findings indicated that 9 μM MNISpd induced apoptosis in HeLa cells during a 48-h period. MNISpd induced apoptosis in HeLa cells following cytochrome c release, elevation of caspase 3/9 activity, apoptosisinducing factor (AIF) translocation and up-/down-regulation of Bax/Bcl-2 protein expression, respectively, and these effects were completely antagonized by pre-incubation with 10 mM NAC for 2 h. MNISpd induced significant ROS accumulation following up-regulation of polyamine oxidase (PAO) activity and complex variations in glutathione levels. It is concluded that MNISpd-induced apoptosis is related to intrinsic caspase-dependent and AIF-mediated caspaseindependent apoptosis pathways in HeLa cells. MNISpdinduced apoptosis correlates to MNISpd-induced ROS production resulting from GSH (reduced form of glutathione) pool depletion, and PAO is likely to be the source of ROS.

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“…Bisnaphthalimidopropyl (BNIP) derivatives have been shown to possess anticancer activity (7)(8)(9)(10)(11) and to have activity against a related trypanosomatid, Leishmania infantum (12)(13)(14). The potential activity of three BNIP derivatives previously synthetized (Ͼ96% pure [10,11,15]), namely, BNIPDiaminobutane (BNIPDabut), BNIPDiaminoheptane (BNIPDahep), and BNIPDiaminooctane (BNIPDaoct) (Fig.…”

mentioning

confidence: 99%

“…The potential activity of three BNIP derivatives previously synthetized (Ͼ96% pure [10,11,15]), namely, BNIPDiaminobutane (BNIPDabut), BNIPDiaminoheptane (BNIPDahep), and BNIPDiaminooctane (BNIPDaoct) (Fig. 1A), against T. brucei brucei Lister 427 bloodstream forms (BSFs), was investigated.…”

mentioning

confidence: 99%

Activity of Bisnaphthalimidopropyl Derivatives against Trypanosoma brucei

Graça¹,

Gaspar²,

Costa³

et al. 2016

Antimicrob Agents Chemother

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g Current treatments for African trypanosomiasis are either toxic, costly, difficult to administer, or prone to elicit resistance. This study evaluated the activity of bisnaphthalimidopropyl (BNIP) derivatives against Trypanosoma brucei. BNIPDiaminobutane (BNIPDabut), the most active of these compounds, showed in vitro inhibition in the single-unit nanomolar range, similar to the activity in the reference drug pentamidine, and presented low toxicity and adequate metabolic stability. Additionally, using a murine model of acute infection and live imaging, a significant decrease in parasite load in BNIPDabut-treated mice was observed. However, cure was not achieved. BNIPDabut constitutes a new scaffold for antitrypanosomal drugs that deserves further consideration.

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

Cited by 28 publications

References 9 publications

Poly(allylamine) Magnetomicelles for Image Guided Drug Delivery

Poly(allylamine) Magnetomicelles for Image Guided Drug Delivery

Reactive oxygen species (ROS) accumulation induced by mononaphthalimide-spermidine leads to intrinsic and AIF-mediated apoptosis in HeLa cells

Activity of Bisnaphthalimidopropyl Derivatives against Trypanosoma brucei

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