Synthesis and antiplasmodial activity of streptocyanine/peroxide and streptocyanine/4-aminoquinoline hybrid dyes

Abstract

Two series of streptocyanine dyes incorporating cyclic peroxide or 4-aminoquinoline moieties are prepared and X-ray diffraction structures for three compounds are determined. All hybrid dyes show good antiplasmodial activity (0.06 to 0.66 μM) and are not or are slightly cytotoxic, except 10a.

Antimalarial Bicyclic Peroxides Belonging to the G-Factor Family: Mechanistic Aspects of their Formation and Iron (II) Induced Reduction

“…All hybrid unsymmetrical molecules 49, 50 and 51 exhibited potent in vitro antiplasmodial activities (0.039 to 0.436 M) similar or better than those of their corresponding streptocyanines 52, 53, 54 (0.085 to 5.47 M). [66] Antiplasmodial activity is not improved by the introduction of two endoperoxide moieties as the hybrid symmetrical compound 48 did not display more potent IC 50 values than its corresponding hybrid unsymmetrical compound 49 or streptocyanine 52. Hybrid peroxo-streptocyanines are thus ten-to one hundred-fold more active than the cyclic peroxide 47 (IC 50 5.7 M) which is likely too hydrophilic due to the NH group.…”

“…Symmetrical (48) and unsymmetrical compounds (49,50,51) were obtained using this strategy. [66] Their antiplasmodial activities, against chloroquine sensitive (Nigerian) and resistant (FcB1-Columbia and FcM29-Cameroon) strains of P. falciparum are presented in Table 3 . All hybrid unsymmetrical molecules 49, 50 and 51 exhibited potent in vitro antiplasmodial activities (0.039 to 0.436 M) similar or better than those of their corresponding streptocyanines 52, 53, 54 (0.085 to 5.47 M).…”

“…The intermediate acids (56,57) were obtained quantitatively by reaction of the succinic anhydride with the two amino derivatives of the 7-chloroquinoline. [66] Then, the coupling was carried out between the amino-endoperoxide 47 and the intermediate acids (56,57) using the reagent HBTU (O-Benzotriazole-N,N,N',N'-tetramethyl-uronium-hexafluoro-phosphate) and di-isopropylethylamine. The second strategy involved linking the 7-chloroquinoline directly or via an amino ethylene coupling arm to the piperidineendoperoxide moiety.…”

Investigation of the grafting of fluorophores onto double-walled carbon nanotubes: The influence of the geometry of the molecules

“…Then, hoping to pave the way toward a better understanding of the parameters that influence the grafting efficiency of the fluorophores onto DWNTs, we chose to study the influence of the geometry by investigating the grafting of a fluorescent molecule owning a very different geometry, the streptocyanine 5Me(NEt 2 ) 2 [11][12][13][14][15]. Indeed, the streptocyanine 5Me(NEt 2 ) 2 exhibits two parallel aromatic 6-carbon rings that are perpendicular to the main carbon chain in witch both nitrogen atoms are not included in conjugated heterocycles, and therefore makes it a worse candidate for its adsorption (particularly via π-π interactions) onto the DWNTs when compared to FITC that has a planar geometry.…”

Comparison of diffusivities data of streptocyanine dyes by electrochemical and NMR-DOSY methods

“…Due to their photophysic properties, this class of compounds presents numerous applications, like photographic sensitizers [3,4], infrared-dyesensitized solar cell [5], optical recording [6], nonlinear frequency doublers [7,8], or biological probes [9][10][11][12]. Cyanines are also known to possess interesting pharmacological properties [13,14].…”