Organic & Biomolecular Chemistry Blog

Prof. Bradley D. Smith and coworkers at University of Notre Dame and Molecular Targeting Technologies, Inc. have modified squaraine rotaxanes with four large stopper groups that provide the much needed long-term, chemical stability in physiological solution. Combined with high quantum yields, excellent excitation/emission wavelength for in vivo analysis, good water-solubility, some of these new dyes undergo rapid renal clearance and very low tissue uptake in living mice, making them excellent fluorescent tracers.

As noted by the authors, the dendritic and polyionic structures of these dyes will also interest and inform the community of scientists who are trying to develop compounds that do not interact with biological surfaces.

A simple and novel approach – Read all the details here – This Hot Article will be free to access for the next 4 weeks

Water-soluble, deep-red fluorescent squaraine rotaxanes
Erin L. Cole, Easwaran Arunkumar, Shuzhang Xiao, Bryan A. Smith and Bradley D. Smith
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C2OB06783H, Communication

CO₂ is an attractive alternative feedstock to oil for the fine chemicals industry, due to its abundance and the fact that it is a waste product in many other industrial processes.  But carbon dioxide’s inertness makes it difficult to realistically use as a C-1 reagent.  In this hot paper Jim Anderson and Rafael Bou Moreno from UCL report advances towards the green dream by synthesising ureas from the reaction of CO₂ with 12- and 14-electron titanium imido complexes.

Download the paper for all the details – it’s free to access for 4 weeks:

Synthesis of ureas from titanium imido complexes using CO₂ as a C-1 reagent at ambient temperature and pressure
James C. Anderson and Rafael Bou Moreno
DOI: 10.1039/C1OB06576A

The groups of Marvin Caruthers (University of Colorado at Boulder, USA) and Michael Gait (Medical Research Council Centre, Cambridge, UK) describe a new chemical synthesis and biological properties of 2’-O-methyl oligoribonucleotides (ORNs) containing internucleotide linkages modified with phosphonoacetate (PACE) and thiophosphonoacetate (thioPACE) groups.

ThioPACE modifications were found to greatly improve the efficiency of cell uptake and the potency of a 2′-O-Me-ORN miRNA122 inhibitor, showing that this class of modifications has great potential for applications in RNA therapeutics research.

As with all our HOT Articles, this OBC article is FREE for you to access, for a period of 4 weeks.

Synthesis and biological activity of phosphonoacetate- and thiophosphonoacetate-modified 2′-O-methyl oligoribonucleotides
Richard N. Threlfall, Adrian G. Torres, Angelika Krivenko, Michael J. Gait and Marvin H. Caruthers
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06614E

In their quest to develop specific ligands for drug target proteins, Professor Satoshi Shuto and coll. have used a stereochemical diversity-oriented conformational restriction strategy to synthesize potent histamine H3 and/or H4 receptor ligands. Some of these cyclopropane-based analogs of histamine with a chiral cis- or trans-2,3-methanobutane backbone show remarkable antagonistic activity towards H3 and H4.

Interested in Medicinal Chemistry and curious about what conformational restriction strategies can do for you?

Then why not read this article, FREE to access for a period of four weeks






Cyclopropane-based stereochemical diversity-oriented conformational restriction strategy: Histamine H3 and/or H4 receptor ligands with the 2,3-methanobutane backbone
Mizuki Watanabe, Takaaki Kobayashi, Takatsugu Hirokawa, Akira Yoshida, Yoshihiko Ito, Shizuo Yamada, Naoki Orimoto, Yasundo Yamasaki, Mitsuhiro Arisawa and Satoshi Shuto
Org. Biomol. Chem., 2012, Advance Article
DOI: 10.1039/C1OB06496G, Paper