C8-alkynyl- and alkylamino substituted 2′-deoxyguanosines: a universal linker for nucleic acids modification

Saitō, Yoshio; Matsumoto, Katsuhiko; Bag, Subhendu Sekhar; Ogasawara, Shinji; Fujimoto, Kenzo; Hanawa, Kazuo; Saito, Isao

doi:10.1016/j.tet.2008.01.091

Cited by 28 publications

(19 citation statements)

References 45 publications

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“…Thus we have focused on the preparation of adenosine and 2 0 -deoxyadenosine derivatives with eNR 2 function on the side chain. One of the most common way of the derivatization of adenosine and 2 0 -deoxyadenosine was the synthesis of their 8-bromo-derivatives [20,21], followed by bromine substitution by various nucleophilic species [22,23] including amines. We have found that 8-bromo-2 0 -deoxyadenosine (4) and 8-bromoadenosine (5) react with ansym-N,N-dimethylethylenediamine leading to new 8-(2-dimethylaminoethyl)aminodeoxyadenosine (6) and adenosine (7), respectively (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

A convenient approach towards boron cluster modifications with adenosine and 2′-deoxyadenosine

Semioshkin¹,

Bregadze²,

Godovikov³

et al. 2011

Journal of Organometallic Chemistry

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Section: Resultsmentioning

confidence: 99%

A convenient approach towards boron cluster modifications with adenosine and 2′-deoxyadenosine

Semioshkin¹,

Bregadze²,

Godovikov³

et al. 2011

Journal of Organometallic Chemistry

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“…Phosphate‐buffered saline (PBS, 100 m M phosphate and 150 m M NaCl, pH 7.4) and the aqueous mobile phases for HPLC were prepared with water purified with a Milli‐Q system (purified to 18.2 MΩ cm). Compounds SR101‐Br, 5‐azidopentylamine, pent‐4‐ynamine, N ‐Boc‐1,5‐pentanediamine, and DEAC‐3‐carboxylic acid were synthesized according to literature procedures 15,40–42. The cyclen derivatives DO3A t Bu‐ N ‐(2‐aminoethyl)ethanamide, DO3A t Bu, and DO3AM were synthesized and provided by the CheMatech company.…”

Section: Methodsmentioning

confidence: 99%

“…SR101‐C 3 ‐CCH: Pent‐4‐ynamine42 was used as the primary amine. The sulforhodamine was recovered as a dark pink amorphous powder (11.5 mg, 57 %).…”

Section: Methodsmentioning

confidence: 99%

Rapid Synthesis of Unsymmetrical Sulforhodamines Through Nucleophilic Amination of a Monobrominated Sulfoxanthene Dye

Chevalier

Renault

Boschetti³

et al. 2014

Eur J Org Chem

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A transition‐metal‐free method for the synthesis of N‐substituted unsymmetrical sulforhodamine fluorophores from an unusual monobrominated sulfoxanthene dye and primary or secondary amines by direct SNAr‐type reactions is presented. The simplicity and effectiveness of this “postamination” procedure were demonstrated through the rapid preparation of a library of multifunctional red‐emitting rhodamine analogues. Some of these analogues are equipped with a reactive handle and retain the two water‐solubilizing sulfonic acid moieties of the starting halogenated derivative; this makes them ideal candidates for biolabeling applications. The potential utility of this expeditious strategy to finely tune the photophysical (Stokes shift) and physicochemical properties (amphiphilic character and water solubility) of the sulforhodamine scaffold was also demonstrated through the appendage of a fluorescent amine to create a fluorescence resonance energy transfer (FRET) pair, a long‐chain amine, and tetraazamacrocycles derived from cyclen.

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“…Finally, inhibitor 23 was prepared and evaluated because the 1,2,3-triazole functionality has also been used as an amide surrogate 24,25 (Scheme 6). Amine 21, prepared by literature methods, 26 was coupled with 3-biphenyl azide using Cucatalyzed Click chemistry to give 22. Installation of the chloroacetamidine pharmacophore then provided inhibitor 23.…”

Section: Acs Medicinal Chemistry Lettersmentioning

confidence: 99%

Cellular Activity of New Small Molecule Protein Arginine Deiminase 3 (PAD3) Inhibitors

Jamali

Khan

Tjin

et al. 2016

ACS Med. Chem. Lett.

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The protein arginine deiminases (PADs) catalyze the post-translational deimination of arginine side chains. Multiple PAD isozymes have been characterized, and abnormal PAD activity has been associated with several human disease states. PAD3 has been characterized as a modulator of cell growth via apoptosis inducing factor and has been implicated in the neurodegenerative response to spinal cord injury. Here, we describe the design, synthesis, and evaluation of conformationally constrained versions of the potent and selective PAD3 inhibitor 2. The cell activity of representative inhibitors in this series was also demonstrated for the first time by rescue of thapsigargin-induced cell death in PAD3-expressing HEK293T cells.

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C8-alkynyl- and alkylamino substituted 2′-deoxyguanosines: a universal linker for nucleic acids modification

Cited by 28 publications

References 45 publications

A convenient approach towards boron cluster modifications with adenosine and 2′-deoxyadenosine

A convenient approach towards boron cluster modifications with adenosine and 2′-deoxyadenosine

Rapid Synthesis of Unsymmetrical Sulforhodamines Through Nucleophilic Amination of a Monobrominated Sulfoxanthene Dye

Cellular Activity of New Small Molecule Protein Arginine Deiminase 3 (PAD3) Inhibitors

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