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The synthesis involved the copper\u2010catalyzed azide\u2010alkyne cycloaddition reaction of a mono\u2010 or dialkynyl zinc(II) phthalocyanine with an acetyl\u2010protected galactosyl azide or its dendritic derivative with four acetyl\u2010protected galactosyl groups, followed by removal of the acetyl protecting groups via alkaline hydrolysis. In <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010dimethylformamide, these oligogalactosyl phthalocyanines were non\u2010aggregated as shown by the strong Q\u2010band absorption and fluorescence emission. Owing to the di\u2010\u03b1\u2010substitution, they also behaved as efficient singlet oxygen generators upon light irradiation with a singlet oxygen quantum yield of 0.84. The spectroscopic and photophysical properties were not affected by the number of galactosyl units. In contrast, the compounds became significantly aggregated and quenched in phosphate\u2010buffered saline. Their cellular uptake was then studied using a range of cell lines, which generally followed the order <jats:bold>Pc\u2010gal<jats:sub>1<\/jats:sub><\/jats:bold>&gt;<jats:bold>Pc\u2010gal<jats:sub>2<\/jats:sub><\/jats:bold>\u2248<jats:bold>Pc\u2010gal<jats:sub>4<\/jats:sub><\/jats:bold>&gt;<jats:bold>Pc\u2010gal<jats:sub>8<\/jats:sub><\/jats:bold>. Interestingly, the di\u2010galactosyl analogue exhibited selective uptake against HeLa human cervical carcinoma cells through an energy\u2010dependent pathway instead of the expected asialoglycoprotein receptor. Upon light irradiation, it could effectively kill the cells with a half\u2010maximal inhibitory concentration of 0.58\u2005\u03bcM.<\/jats:p>","DOI":"10.1002\/cplu.202200285","type":"journal-article","created":{"date-parts":[[2022,9,22]],"date-time":"2022-09-22T04:11:16Z","timestamp":1663819876000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Synthesis, Cellular Uptake, and Photodynamic Activity of Oligogalactosyl Zinc(II) Phthalocyanines"],"prefix":"10.1002","volume":"88","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7575-5000","authenticated-orcid":false,"given":"Junlong","family":"Xiong","sequence":"first","affiliation":[{"name":"Department of Chemistry The Chinese University of Hong Kong  Shatin, N.T. Hong Kong P. R. 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