A simple method for introducing a thiol group at the 5′-end of synthetic oligonucleotides

Kumar, A; Advani, Sonia; Dawar, Hema; Talwar, G.P.

doi:10.1093/nar/19.16.4561

Cited by 26 publications

(10 citation statements)

References 5 publications

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“…Similarly, free thiols can be introduced by first reacting 2-iminothiolane to primary amines, but this approach introduces a positive charge on the NP-ligand construct [181]. Other chemical efforts have also been reported for introducing thiols to molecules [182]. …”

Section: Active Targeting: Toward Magic Bullet?mentioning

confidence: 99%

Cancer nanotechnology: The impact of passive and active targeting in the era of modern cancer biology

Bertrand

et al. 2014

Advanced Drug Delivery Reviews

2,366

1,814

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Cancer nanotherapeutics are progressing at a steady rate; research and development in the field has experienced an exponential growth since early 2000’s. The path to the commercialization of oncology drugs is long and carries significant risk; however, there is considerable excitement that nanoparticle technologies may contribute to the success of cancer drug development. The pace at which pharmaceutical companies have formed partnerships to use proprietary nanoparticle technologies has considerably accelerated. It is now recognized that by enhancing the efficacy and/or tolerability of new drug candidates, nanotechnology can meaningfully contribute to create differentiated products and improve clinical outcome. This review describes the lessons learned since the commercialization of the first-generation nanomedicines including DOXIL® and Abraxane®. It explores our current understanding of targeted and non-targeted nanoparticles that are under various stages of development, including BIND-014 and MM-398. It highlights the opportunities and challenges faced by nanomedicines in contemporary oncology, where personalized medicine is increasingly the mainstay of cancer therapy. We revisit the fundamental concepts of enhanced permeability and retention effect (EPR) and explore the mechanisms proposed to enhance preferential “retention” in the tumor, whether using active targeting of nanoparticles, binding of drugs to their tumoral targets or the presence of tumor associated macrophages. The overall objective of this review is to enhance our understanding in the design and development of therapeutic nanoparticles for treatment of cancers.

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Section: Active Targeting: Toward Magic Bullet?mentioning

confidence: 99%

Cancer nanotechnology: The impact of passive and active targeting in the era of modern cancer biology

Bertrand

et al. 2014

Advanced Drug Delivery Reviews

2,366

1,814

View full text Add to dashboard Cite

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“…For example, a report published in 1991 describes the modification with N-acetyl-Hcy-thiolactone as a facile method to introduce a thiol group at the 5 0 -end of an oligonucleotide, which, in contrast to other methods, does not require the deprotection step [209]. An oligonucleotide is synthesized using the phosphoramidite method, and an amino group is introduced using the amino modifier II.…”

Section: Reactivity Toward Amino Groupsmentioning

confidence: 99%

Homocysteine in Protein Structure/Function and Human Disease

Jakubowski¹

2013

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“…For the synthesis of oligonucleotides with a sulfhydryl containing moiety at the 5= end, different approaches are possible [12,13]. We chose a method where first a protected oligonucleotide is synthesized, followed by the attachment of the R-S-S-(CH 2 ) 11 -group (Scheme 1).…”

Section: Oligonucleotide Synthesismentioning

confidence: 99%

Characterization and sequence verification of thiolated deoxyoligonucleotides used for microarray construction

Rozenski

2006

J. Am. Soc. Mass Spectrom.

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During synthesis of thiolated deoxyoligonucleotides, side products can be formed. When used in the fabrication of microchips, the oligonucleotides have to be of high purity. We demonstrated the presence of impurities, which were not failure sequences from the synthesis. These products were identified and characterized using high-performance liquid chromatography (HPLC) and electrospray MS(/MS). The presence of the free thiol group was assessed by acrylamide derivatization. After reaction with acrylamide the correct compounds showed a 71 u mass shift and the major fragment ions could be assigned as 5= a-base and 3= w ions, similar as for unmodified DNA. The side products were unaffected by acrylamide, suggesting that the thiol group was modified. The oligonucleotide containing a species with a mass of 32 u higher was identified as 5= sulfinic acid containing molecule and was found as 45% of the total amount of a DNA 25 mer. Other components appeared to be dithio-linked oxidation products, present about 1 to 5% in a 10 mer and 15 mer deoxyoligonucleotide. The analyses were useful for optimizing the synthesis

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A simple method for introducing a thiol group at the 5′-end of synthetic oligonucleotides

Abstract: Several methods have been devised to introduce a thiol group at the 5'-end of an oligonucleotide (1, 2, 3). However, all the methods reported to date require a deprotection step after the completion of the reaction. Here we report a simple method for

Cited by 26 publications

References 5 publications

Cancer nanotechnology: The impact of passive and active targeting in the era of modern cancer biology

Cancer nanotechnology: The impact of passive and active targeting in the era of modern cancer biology

Homocysteine in Protein Structure/Function and Human Disease

Characterization and sequence verification of thiolated deoxyoligonucleotides used for microarray construction

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