Bioconjugate Chemistry

Kneuer, C., Sameti, M., Bakowsky, U., Schiestel, T., Schirra, H., Schmidt, H., and Lehr, C.M., Surface modified silica-nanoparticles can enhance transfection in vitro a novel class of non-viral DNA vectors, Bioconjugate Chemistry, 2000, 11, 926-932. 

Haensler, J., and Szoka Jr., F.C., Polyamidoamine cascade polymers mediate efficient transfection of cells in culture, Bioconjugate Chemistry, 1993, 4, 372-379. 

The power and advantages of assessing cellular processes at their most fundamental level is propelling the science of oligonucleotide probe detection into one of the most prominent positions in bioconjugate chemistry. Oligonucleotide arrays containing hundreds or thousands of... 

Ultimately, this section is meant to function as a ready-reference database for learning or review of bioconjugate chemistry. In this regard, a reaction can be quickly found, a short discussion of its properties and use read, and a visual representation of the chemistry of bond formation illustrated. What this section is not meant to be is an exhaustive discussion on the theory or mechanism behind each reaction, nor a review of every application in which each chemical reaction has been used. For particular applications where the chemistries are employed, cross-references are given to other sections in this book or to outside literature sources. 

Sonvico F, Mornet S, Vasseur S, Dubernet C, Jaillard D, Degrouard J, Hoebeke J, Duguet E, Colombo P, Couvreur P (2005) Folate-conjugated iron oxide nanoparticles for solid tumor targeting as potential specific magnetic hyperthermia mediators synthesis, physicochemical characterization, and in vitro experiments. Bioconjugate Chemistry 16 1181-1188. 

Hoffmann, K., Soil, R.M., Beck-Sickinger, A.G. and Jung, M. (2001) Fluorescence-labeled octapeptides as substrates for histone deacetylase. Bioconjugate Chemistry, 12, 51-55. 

Addition of a nucleophile to the C-6 position of cytosine often results in fascile displacement reactions occurring at the N4 location. With hydroxylamine attack, nucleophilic displacement causes the formation of an N4-hydroxy derivative. A particularly important reaction for bioconjugate chemistry, however, is that of nucleophilic bisulfite addition to the C-6 position. Sulfonation of cytosine can lead to two distinct reaction products. At acid pH wherein the N-3 nitrogen is protonated, bisulfite reaction results in the 6-sulfonate product followed by spontaneous hydrolysis. Raising the pH to alkaline conditions causes effective formation of uracil. If bisulfite addition is done in the presence of a nucleophile, such as a primary amine or hydrazide compound, then transamination at the N4 position can take place instead of hydrolysis (Fig. 38). This is an important mechanism for adding spacer arm functionalities and other small molecules to cytosine-containing oligonucleotides (see Chapter 17, Section 2.1). 

Carbodiimide-mediated amide bond formation effectively occurs between pH 4.5 and 7.5. Buffer systems using MES or phosphate may be used to stabilize the pH during the course of the reaction. For additional information on specific carbodiimides used in bioconjugate chemistry, see Chapter 3, Section 1. 

Figure 338 The major functional groups of lipids that may participate in bioconjugate chemistries include amines, carboxylates, and hydroxyls.

The first book to capture the entire field of bioconjugate chemistry in a single volume... 

Zhu H, Srivastava R, Brown JQ, McShane MJ. Combined physical and chemical immobihzation of glucose oxidase in alginate microspheres improves stability of encapsulation and activity. Bioconjugate Chemistry 2005, 16, 1451-1458. 

Mujumdar RB, Ernst LA, Mujumdar SR, Lewis CJ, Waggoner AS. Cyanine dye labeling reagents sulfoindocyanine succinimidyl esters. Bioconjugate Chemistry 1993, 4, 105-111. 

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