2,2′-Dipicolylamine (DPA) Oligo Modification
2,2′-Dipicolylamine (DPA) is a tridentate metal-chelating ligand widely used in chemical biology, molecular imaging, biosensor development, and nanotechnology. When conjugated to DNA, RNA, PNA, or other synthetic oligonucleotides, DPA provides a versatile functional group capable of coordinating divalent metal ions, particularly zinc (Zn²⁺). The resulting metal complexes can be exploited for selective molecular recognition, fluorescence sensing, and targeted biological interactions.
DPA consists of two pyridine rings linked through a central amine nitrogen, forming a ligand that binds transition metals with high affinity. In many biological applications, Zn²⁺-DPA complexes exhibit strong affinity for anionic phospholipids, especially phosphatidylserine (PS), which becomes exposed on the surface of apoptotic cells and certain microorganisms. Consequently, DPA-conjugated oligonucleotides have been investigated for apoptosis imaging, bacterial detection, cell-surface targeting, and molecular diagnostics.
When incorporated into oligonucleotides, 2,2′-Dipicolylamine enables researchers to develop multifunctional constructs that combine sequence-specific nucleic acid recognition with metal-mediated targeting or sensing capabilities. DPA modifications are frequently combined with fluorescent dyes, quenchers, biotin, PEG linkers, click chemistry handles, and other conjugation chemistries to produce advanced probes for imaging and analytical applications.
Typical applications include:
- Zinc ion (Zn²⁺) sensing
- Fluorescent biosensors
- Molecular imaging
- Apoptotic cell recognition
- Phosphatidylserine (PS) targeting
- Bacterial membrane targeting
- DNA nanotechnology
- Targeted bioconjugation
- Metal-responsive molecular probes
- Diagnostic assay development
Bio-Synthesis offers custom DPA oligonucleotide conjugation using appropriate linker chemistries at the 5′ end, 3′ end, or selected internal positions. DPA modifications can be incorporated into DNA, RNA, antisense oligonucleotides (ASOs), aptamers, siRNA, PNA, and other synthetic nucleic acids. Depending on project requirements, DPA may be combined with fluorophores, affinity tags, peptides, lipids, nanoparticles, or additional functional groups to create highly specialized research reagents.
Each DPA-modified oligonucleotide is synthesized using optimized conjugation protocols and can be purified by HPLC or PAGE, followed by analytical characterization using LC-MS, MALDI-TOF, UV spectroscopy, or other quality control methods as appropriate.
Product Information
2,2′-Dipicolylamine (DPA) Oligo Modification
-20°C To -70°C
Oligonucleotides are stable in solution at 4°C for up to 2 weeks. Properly reconstituted material stored at -20°C should be stable for at least 6 months. Dried DNA (when kept at 20°C) in a nuclease-free environment should be stable for years.
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dT Ferrocene Oligonucleotide Modification
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DOTA, Tetraazacyclododecane-1,4,7,10-tetraacetic acid
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NOTA, 1,4,7-triazacyclononane-N,N',N''-triacetic acid
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TETA, 1,4,8,11-tetraazacyclotetradecane-N,N',N'',N'''-tetraacetic acid
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References/Citations:
- Smith BD, et al. Targeted imaging of cell death using zinc(II)-dipicolylamine coordination complexes. Accounts of Chemical Research. 2010;43(5):629–638. DOI: 10.1021/ar900221m
- Ojida A, Hamachi I. Design and applications of zinc–dipicolylamine complexes for molecular recognition and sensing. Accounts of Chemical Research.
- Kikuchi K, Komatsu K, Nagano T. Zinc sensing for cellular applications using dipicolylamine-based probes. Current Opinion in Chemical Biology.
- Hermanson GT. Bioconjugate Techniques. 3rd ed. Academic Press; 2013.
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