N-(Iodoacetyl)-N‘-(anthraquinon-2-oyl)-ethylenediamine (IAED):  A New Heterobifunctional Reagent for the Preparation of Biochips

Abstract

Design and synthesis of a new heterobifunctional reagent, N-(iodoacetyl)-N'-(anthraquinon-2-oyl)-ethylenediamine (IAED), have been described for the preparation of oligonucleotide-based biochips. The performance of the featured reagent is probed by the immobilization of thiolated and thiophosphorylated oligonucleotides on modified glass microslides via two routes (routes A and B). The immobilization procedure was accelerated by performing a chemical reaction between thiolated oligomers and the iodoacetyl moiety of the reagent under microwaves (MW), where it is completed in just 10 min. The quality of the constructed oligonucleotide microarrays was tested by performing a hybridization assay with a complementary target and subsequently used for the detection of base mismatches. The immobilized probes were found to be thermally stable.

Chemical strategies for immobilization of oligonucleotides

“…Both routes work satisfactorily. On the parallel lines, Patnaik et al [88] recently reported the synthesis and application of a new heterobifunctional reagent, N-(iodoacetyl)-N'-(anthraquinon-2-oyl)-ethylenediamine (IAED) 44, for immobilization ( Fig. 21).…”

Synthesis of Functionalized Anthraquinones via Coupling Reactions of 2,6-Diiodo-1,5-dioctyloxy-9,10-anthraquinone

“…1 H NMR (500 MHz, CDCl 3 ): d = 0.90 (t, J = 6.2 Hz, 6 H), 1.27-1.38 (m, 16 H), 1.30-1.54 (m, 4 H), 1.80 (quint, J = 6.2 Hz, 4 H), 4.07 (t, J = 6.2 Hz, 4 H), 7.03 (dd, J = 5.1, 3.6 Hz, 2 H), 7.05-7.09 (m, 2 H), 7.11 (d, J = 8.8 Hz, 2 H), 7.32 (dd, J = 5.1, 1.1 Hz, 2 H), 7.55 (d, J = 8.8 Hz, 2 H). 13 C NMR (125 MHz, CDCl 3 ): 22.8, 26.0, 29.2, 29.4, 29.5, 32.0, 69.4, 116.4, 124.8, 125.4, 125.6, 127.1, 127.2, 137.2, 137.3, 141.2, 151.2, 185.0.…”

“…1 H NMR (500 MHz, CDCl 3 ): d = 0.85 (t, J = 7.0 Hz, 6 H), 1.20-1.38 (m, 16 H), 1.56 (quint, J = 7.0 Hz, 4 H), 1.91 (quint, J = 7.0 Hz, 4 H), 4.12 (t, J = 7.0 Hz, 4 H), 7.14 (d, J = 8.8 Hz, 2 H), 7.33-7.38 (m, 6 H), 7.62-7.67 (m, 4 H), 7.74 (d, J = 8.8 Hz, 2 H). 13 C NMR (125 MHz, CDCl 3 ): d = 14.1, 22.6, 25.9, 29.2, 29.4, 29.7, 31.8, 69.7, 88.3, 92.4, 113.5, 116.8, 123.5, 123.7, 128.2, 131.8, 139.2, 157.8, 182.4.…”

“…In fact, various 9,10-anthraquinone derivatives have been investigated and used as antibiotics, 1 anticancer agents, 2 DNA photocleaving oxidants 3 or DNA intercalators, 4 as well as algicides, 5 organogelators, 6 pigments in the dyestuff and textile industry, 7 or organic stabilizers against photodegradation of polymers. 8 Furthermore, molecular, polymeric, and supramolecular 9,10-anthraquinone-based systems have recently attracted considerable interest for their potential use as liquid crystals, 9 redox switches 10 for molecular electronics, chelating agents 11 or ionophores 12 for selective cation sensing, heterobifunctional reagents for preparation of biochips, 13 near infrared absorbing dyes 14 for optical data storage, or guest nonlinear optical dyes. 15 Recently, donor-anthraquinone acceptor 16 dyads or triads with photoinduced charge transfer properties have also been reported for applications in photovoltaic cells.…”

“…22-1.40 (m, 16 H), 1.42-1.51 (m, 4 H), 1.80 (quint, J = 6.4 Hz, 4 H), 4.09 (t, J = 6.4 Hz, 4 H), 7.15 (d, J = 8.8 Hz, 2 H), 7.31-7.41 (m, 10 H), 7.46 (d, J = 8.8 Hz, 2 H). 13 C NMR (125 MHz, CDCl 3 ): d = 14.1, 22.7, 25.8, 29.1, 29.2, 29.4, 31.9, 69.4, 116.3, 124.7, 126.8, 128.0, 129.2, 133.3, 136.4, 137.0, 140.2, 156.6, 185.6. Anal Calcd for C 42 H 48 O 4 : C, 81.78; H, 7.84. Found: C, 81.83; H, 7.82.…”