1,3-dipolar cycloaddition in the synthesis of glycoconjugates of natural chlorins and bacteriochlorins

Mikhail A. Grin, Ivan S. Lonin, Anna A. Lakhina, Elena S. Ol'shanskaya, Alexey I. Makarov, Yury L. Sebyakin, Lyudmila Yu Guryeva, Philip V. Toukach, Alexey S. Kononikhin, Vladimir A. Kuzmin, Andrey F. Mironov

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

Glucose-, galactose- and lactose-containing photosensitizers based on derivatives of chlorophyll a and bacteriochlorophyll a were synthesized with the use of [3+2] cycloaddition between sugar azides and triple bond derivatives of chlorins and bacteriochlorins. Unlike bacteriochlorin cycloimide, chlorin was detected to form a Cu-complex during the click reaction. An approach to the synthesis of metal-free glycosylated chlorins was developed with the use of "protection" by Zn2+ cation and subsequent demetalation. It is based on the action of alkynyl chlorin e6 derivative Zn-complex, which is resistant to the substitution by copper cation. Bacteriochlorin p cycloimide conjugate with per-acetylated β-D-lactose was obtained and shown to become water-soluble after unblocking of the lactose hydroxy functions. NMR studies allowed for the elucidation of structure, tautomeric form and conformation of the obtained compounds.

Original languageEnglish
Pages (from-to)336-345
Number of pages10
JournalJournal of Porphyrins and Phthalocyanines
Volume13
Issue number3
DOIs
Publication statusPublished - Mar 2009
Externally publishedYes

Keywords

  • bacteriopurpurinimide
  • click chemistry
  • galactose
  • glucose
  • glycoconjugates
  • lactose
  • photodynamic therapy of cancer
  • photosensitizers
  • triazole

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