Chemical Modification of M13 Bacteriophage and Its Application in Cancer Cell Imaging

The M13 bacteriophage has been demonstrated to be a robust scaffold for bionanomaterial development. In this paper, we report on the chemical modifications of three kinds of reactive groups, i.e., the amino groups of lysine residues or N-terminal, the carboxylic acid groups of aspartic acid or gluta...

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Published inBioconjugate chemistry Vol. 21; no. 7; pp. 1369 - 1377
Main Authors Li, Kai, Chen, Yi, Li, Siqi, Nguyen, Huong Giang, Niu, Zhongwei, You, Shaojin, Mello, Charlene M, Lu, Xiaobing, Wang, Qian
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 21.07.2010
Subjects
Bacteria
Bacteriophage M13 - chemistry
Cancer
Carboxylic acids
Cells
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Folic acid
Folic Acid - chemistry
HeLa Cells
Humans
Liquid chromatography
Medical imaging
Molecular Imaging - methods
Molecular Structure
Molecules
Neoplasms - pathology
Particle Size
Phenols
Stereoisomerism
Surface Properties
Tumor Cells, Cultured
Vitamin B
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Summary:The M13 bacteriophage has been demonstrated to be a robust scaffold for bionanomaterial development. In this paper, we report on the chemical modifications of three kinds of reactive groups, i.e., the amino groups of lysine residues or N-terminal, the carboxylic acid groups of aspartic acid or glutamic acid residues, and the phenol group of tyrosine residues, on M13 surface. The reactivity of each group was identified through conjugation with small fluorescent molecules. Furthermore, the regioselectivity of each reaction was investigated by HPLC-MS-MS. By optimizing the reaction condition, hundreds of fluorescent moieties could be attached to create a highly fluorescent M13 bacteriophage. In addition, cancer cell targeting motifs such as folic acid could also be conjugated onto the M13 surface. Therefore, dual-modified M13 particles with folic acid and fluorescent molecules were synthesized via the selective modification of two kinds of reactive groups. Such dual-modified M13 particles showed very good binding affinity to human KB cancer cells, which demonstrated the potential applications of M13 bacteriophage in bioimaging and drug delivery.
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ISSN:1043-1802
1520-4812
1520-4812
DOI:10.1021/bc900405q