Archive for August, 2013

Hydrogel treatment targets tumours

Hydrogels of cancer drug taxol injected directly into tumours have been shown to be more effective at inhibiting tumour growth than intravenous taxol injections of four times the dosage.

target-injection-bullseye_shutterstock_101348851_300

Taxol is used to treat many forms of cancer, including breast, lung and ovarian cancer. Its administration is typically every three weeks by intravenous injection and it can take several hours to achieve the required dose.

Hydrogels have great potential to reduce the dosing frequency of chemotherapy. They can hold exceptionally high drug loadings that are released in a controlled and sustained manner. However, synthesising such hydrogels is complex, ultimately resulting in low yields.

Zhimou Yang and fellow researchers at Nankai University in China have successfully simplified the synthesis of taxol hydrogels. Their hydrogel contains taxol conjugated to folic acid. The folic acid facilitates tumour targeting as many cancer cells have folic acid receptors so the hydrogels will sustainably release their taxol cargo through ester bond hydrolysis at the site of cancer cells.

Read the full article on Chemistry World.

Disulfide bond reduction-triggered molecular hydrogels of Folic acid-Taxol conjugates
Chengbiao Yang et al.
DOI: 10.1039/C3OB40969D

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HOT Organic & Biomolecular Chemistry articles for August

Pd(0)-catalyzed benzylic arylation–oxidation of 4-methylquinazolines via sp3 C–H activation under air conditions
Dan Zhao, Min-Xue Zhu, Yue Wang, Qi Shen and Jian-Xin Li
Org. Biomol. Chem., 2013,11, 6246-6249
DOI: 10.1039/C3OB41488D, Communication 

  


Major mechanistic differences between the reactions of hydroxylamine with phosphate di- and tri-esters
Michelle Medeiros, Eduardo H. Wanderlind, José R. Mora, Raphaell Moreira, Anthony J. Kirby and Faruk Nome
Org. Biomol. Chem., 2013,11, 6272-6284
DOI: 10.1039/C3OB40988K, Paper
From themed collection In Celebration of Andrew D. Hamilton’s Career in Chemistry  

 


Novel synthesis of various orthogonally protected Cα-methyllysine analogues and biological evaluation of a Vapreotide analogue containing (S)-α-methyllysine
Souvik Banerjee, Walker J. Wiggins, Jessie L. Geoghegan, Catherine T. Anthony, Eugene A. Woltering and Douglas S. Masterson
Org. Biomol. Chem., 2013,11, 6307-6319
DOI: 10.1039/C3OB41282B, Paper


Synthesis of novel pyrazole-based heterocycles via a copper(II)-catalysed domino annulation
Márió Gyuris, László G. Puskás, Gábor K. Tóth and Iván Kanizsai
Org. Biomol. Chem., 2013,11, 6320-6327
DOI: 10.1039/C3OB41146J, Paper


Structure–activity studies of 4-phenyl-substituted 2′-benzoylpyridine thiosemicarbazones with potent and selective anti-tumour activity
Adeline Y. Lukmantara, Danuta S. Kalinowski, Naresh Kumar and Des R. Richardson
Org. Biomol. Chem., 2013,11, 6414-6425
DOI: 10.1039/C3OB41109E, Paper

 


Transport of macrocyclic compounds across phospholipid bilayers by umbrella-rotaxanes
Christine Chhun, Josée Richard-Daniel, Julie Kempf and Andreea R. Schmitzer
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB41209A, Paper

 


Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity
Steven Gunawan and Christopher Hulme
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB40900G, Paper 

 


Comparative in vitro studies of MR imaging probes for metabotropic glutamate subtype-5 receptor targeting
Sven Gottschalk, Jörn Engelmann, Gabriele A. Rolla, Mauro Botta, David Parker and Anurag Mishra
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB41297K, Paper 

 


Synthesis and biological evaluation of non-isomerizable analogues of Ala-tRNAAla
Denia Mellal, Matthieu Fonvielle, Marco Santarem, Maryline Chemama, Yoann Schneider, Laura Iannazzo, Emmanuelle Braud, Michel Arthur and Mélanie Etheve-Quelquejeu
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB41206G, Paper 

 


First synthesis of antitumoral dasyscyphin B
Ali Akhaouzan, Antonio Fernández, Ahmed I. Mansour, Esteban Alvarez, Ali Haidöur, Ramón Alvarez-Manzaneda, Rachid Chahboun and Enrique Alvarez-Manzaneda
Org. Biomol. Chem., 2013, Advance Article
DOI: 10.1039/C3OB41290C, Paper                                          

Open Access  

 

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In Celebration of Andrew D. Hamilton’s Career in Chemistry

Professor Andrew D. Hamilton FRS

We are delighted to present an on-line collection of articles dedicated to Professor Andrew D. Hamilton FRS, on the occasion of his 60th birthday. 

Students and colleagues past and present have come together to contribute over 40 communications, full papers, feature articles and perspectives of some of their latest work now published in ChemComm, OBC, MedChemComm and RSC Advances.

“An insight into the rise of a star in molecular recognition, ground breaking discoveries, and on a more light-hearted note, some fond reminiscences of research in Cambridge, Princeton, Pittsburgh, Yale and Oxford.”  

Read the introductory Profile article by guest-editors Sam Thompson and Andrew J. Wilson, with the contribution of Sir Alan R. Battersby. 

Access the full collection here

As a taster, the collection of articles includes: 

Chemical approaches for detection and destruction of nerve agents
Dariush Ajami and Julius Rebek
Org. Biomol. Chem., 2013,11, 3936-3942
DOI: 10.1039/C3OB40324F 

Diverse topologies in dynamic combinatorial libraries from tri- and mono-thiols in water: sensitivity to weak supramolecular interactions
Artur R. Stefankiewicz and Jeremy K. M. Sanders
Chem. Commun., 2013,49, 5820-5822
DOI: 10.1039/C3CC41158C 

Peptides: minimal drug surrogates to interrogate and interfere with protein function
A. Cruz-Migoni, N. Fuentes-Fernandez and T. H. Rabbitts
Med. Chem. Commun., 2013,4, 1218-1221
DOI: 10.1039/C3MD00142C 

A rotaxane host system containing integrated triazole C–H hydrogen bond donors for anion recognition
Nicholas G. White and Paul D. Beer
Org. Biomol. Chem., 2013,11, 1326-1333
DOI: 10.1039/C2OB27229F, Paper 

Supramolecular hydrogels based on bola-amphiphilic glycolipids showing color change in response to glycosidases
Rika Ochi, Kazuya Kurotani, Masato Ikeda, Shigeki Kiyonaka and Itaru Hamachi
Chem. Commun., 2013,49, 2115-2117
DOI: 10.1039/C2CC37908B, Communication 

Identification of a potent salicylic acid-based inhibitor of tyrosine phosphatase PTP1B
Sina Haftchenary, Daniel P. Ball, Isabelle Aubry, Melissa Landry, Vijay M. Shahani, Steven Fletcher, Brent D. G. Page, Andriana O. Jouk, Michel L. Tremblay and Patrick T. Gunning
Med. Chem. Commun., 2013,4, 987-992
DOI: 10.1039/C3MD00011G 

and many more!  

Why not have a look at the great cover artworks authors have created to illustrate their articles from the collection – click on the images to access the articles! 

           

Feel free to send the link to the issue to other researchers whom you think will find it interesting and stimulating to read.

We hope you enjoy the collection!

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Tethered aldo/keto-acids/esters unlock new bis-hetrocyclic tetrazolo scaffolds

The classical Ugi multi-component reaction can be used to generate a peptidic-like molecule, with 4 points of diversification, from an aldehyde, an amine, an isocyanide and a carboxylic acid. In the Ugi-azide reaction, the carboxylic acid is replaced with trimethylsilyl azide, providing a convenient route to 1,5-disubstituted tetrazoles. This scaffold is a bioisostere for the cis-amide bond.

In the HOT article, Gunawan and Hulme report the use of Ugi-azide reactions to generate a series of different bis-hetrocyclic tetrazolo scaffolds, facilitated by variation of the linker group in the aldo/keto-acids/esters. These scaffolds may aid the development of new molecular probes for the investigation of peptidergic biological systems.

Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity

Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity
Steven Gunawan and Christopher Hulme
DOI: 10.1039/C3OB40900G

Free to access for 4 weeks

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Q2 Top 10 for Organic & Biomolecular Chemistry

Please take a look at the top 10 most accessed Organic & Biomolecular Chemistry articles for the second quarter of 2013:

Synthetic applications of photoredox catalysis with visible light  
Yumeng Xi, Hong Yi and Aiwen Lei  
Org. Biomol. Chem., 2013, 11, 2387-2403  
DOI: 10.1039/C3OB40137E 

Redesign of enzyme for improving catalytic activity and enantioselectivity toward poor substrates: manipulation of the transition state  
Tadashi Ema, Yasuko Nakano, Daiki Yoshida, Shusuke Kamata and Takashi Sakai  
Org. Biomol. Chem., 2012, 10, 6299-6308  
DOI: 10.1039/C2OB25614B 

Recent advances in the synthesis of aromatic nitro compounds  
Guobing Yan and Minghua Yang  
Org. Biomol. Chem., 2013, 11, 2554-2566  
DOI: 10.1039/C3OB27354G 

Expeditious synthesis of bacterial, rare sugar building blocks to access the prokaryotic glycome  
Madhu Emmadi and Suvarn S. Kulkarni  
Org. Biomol. Chem., 2013, 11, 3098-3102  
DOI: 10.1039/C3OB40615F 

Transition metal-catalyzed functionalization of pyrazines  
Nicolai I. Nikishkin, Jurriaan Huskens and Willem Verboom   
Org. Biomol. Chem., 2013, 11, 3583-3602  
DOI: 10.1039/C3OB40460A 

New trends in bismuth-catalyzed synthetic transformations  
Thierry Ollevier 
Org. Biomol. Chem., 2013, 11, 2740-2755  
DOI: 10.1039/C3OB26537D 

Synthesis and biological evaluation of new paclitaxel analogs and discovery of potent antitumor agents  
Kyriacos C. Nicolaou and Roman A. Valiulin 
Org. Biomol. Chem., 2013, 11, 4154-4163  
DOI: 10.1039/C3OB40654G 

Manipulating non-innocent π-spacers: the challenges of using 2,6-disubstituted BODIPY cores within donor–acceptor light-harvesting motifs  
Catherine Bonnier, Devin D. Machin, Omar Abdi and Bryan D. Koivisto 
Org. Biomol. Chem., 2013, 11, 3756-3760  
DOI: 10.1039/C3OB40213D 

Bu4NI-catalyzed decarboxylative acyloxylation of an sp3 C–H bond adjacent to a heteroatom with α-oxocarboxylic acids  
Shuai Zhang, Li-Na Guo, Hua Wang and Xin-Hua Duan 
Org. Biomol. Chem., 2013, 11, 4308-4311  
DOI: 10.1039/C3OB40748A 

Recent applications of arene diazonium salts in organic synthesis  
Fanyang Mo, Guangbin Dong, Yan Zhang and Jianbo Wang 
Org. Biomol. Chem., 2013, 11, 1582-1593  
DOI: 10.1039/C3OB27366K

We would very much welcome your thoughts and comments below.

Fancy submitting an article to Organic & Biomolecular Chemistry? Then why not submit to us today or alternatively email us your suggestions.

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