Literature DB >> 11738607

Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy.

I Sylvain1, R Zerrouki, R Granet, Y M Huang, J-F Lagorce, M Guilloton, J-C Blais, P Krausz.   

Abstract

The aim of this work is the synthesis of a new family of glycosylated porphyrins in which the sugar moieties are linked to the tetrapyrrole ring by a thioglycosidic bond. Two series have been designed. The first one corresponds to meso-aryl porphyrin derivatives. The second one has been obtained from protoporphyrin IX derivatization. Aryl-porphyrins were prepared from tristolyl o- and p-hydroxyporphyrins followed by bromoallylation and thioglycosylation with peracetylated S-glucose, mannose and galactose and deprotection. The other series has been synthesized from protoporphyrin IX dimethylester with a regioselective glycosylation of terminal alkenyl carbon. The UV-visible, NMR and MALDI mass spectra are presented. Photocytotoxicities of the synthesized compounds against K562 chronic leukaemia cell line has been evaluated.

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Year:  2002        PMID： 11738607     DOI： 10.1016/s0968-0896(01)00255-3

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  7 in total

Review 1.  Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics.

Authors:  Sunaina Singh; Amit Aggarwal; N V S Dinesh K Bhupathiraju; Gianluca Arianna; Kirran Tiwari; Charles Michael Drain
Journal:  Chem Rev       Date:  2015-08-28       Impact factor: 60.622

2.  Efficient microwave-assisted synthesis of amine-substituted tetrakis(pentafluorophenyl)porphyrin.

Authors:  Diana Samaroo; Clifford E Soll; Louis J Todaro; Charles M Drain
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

3.  Efficient synthesis and photodynamic activity of porphyrin-saccharide conjugates: targeting and incapacitating cancer cells.

Authors:  Xin Chen; Li Hui; David A Foster; Charles Michael Drain
Journal:  Biochemistry       Date:  2004-08-31       Impact factor: 3.162

4.  Conjugation of 2-(1'-hexyloxyethyl)-2-devinylpyropheophorbide-a (HPPH) to carbohydrates changes its subcellular distribution and enhances photodynamic activity in vivo.

Authors:  Xiang Zheng; Janet Morgan; Suresh K Pandey; Yihui Chen; Erin Tracy; Heinz Baumann; Joseph R Missert; Carrie Batt; Jennifer Jackson; David A Bellnier; Barbara W Henderson; Ravindra K Pandey
Journal:  J Med Chem       Date:  2009-07-23       Impact factor: 7.446

5.  Solvent-Tuned Self-Assembled Nanostructures of Chiral l/d-Phenylalanine Derivatives of Protoporphyrin IX.

Authors:  Mr Sharad R Bobe; Mohammad Al Kobaisi; Sheshanath V Bhosale; Sidhanath V Bhosale
Journal:  ChemistryOpen       Date:  2015-03-14       Impact factor: 2.911

Review 6.  Chemical approaches for the enhancement of porphyrin skeleton-based photodynamic therapy.

Authors:  Yuyan Lin; Tao Zhou; Renren Bai; Yuanyuan Xie
Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051

7.  Studies towards elucidating the potential of 5,10,15,20-tetrakis(p-carboxy-methyleneoxyphenyl)porphyrin as a theranostic agent for applications in PET and PDT.

Authors:  Mohini Guleria; Chandan Kumar; Tapas Das; Jeyachitra Amirdhanayagam; Rohit Sharma; Haladhar D Sarma; Ashutosh Dash
Journal:  Medchemcomm       Date:  2018-02-12       Impact factor: 3.597
  7 in total

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