Biotinylated Chlorin and Its Zinc and Indium Complexes: Synthesis and In Vitro Biological Evaluation for Photodynamic Therapy

Isaac-Lam, Meden F.; Hammonds, Dewana M

doi:10.3390/ph10020041

Cited by 21 publications

(20 citation statements)

References 42 publications

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“…Results are already published elsewhere. 35,36 The vitamins (BTN and PA), coenzyme LA, and bexarotene (BX; Vit A analogue) were covalently appended to the 13 1 position of the chlorin macrocycle via a hexyl diamine linker.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Photodynamic Activity of Vitamin–Chlorin Conjugates at Nanomolar Concentrations against Prostate Cancer Cells

Isaac-Lam

Hammonds

2019

ACS Omega

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Phototoxicity response of synthesized vitamin–chlorin conjugates and their zinc and indium complexes was determined in the human PC-3 prostate cancer cell line, which was previously demonstrated to overexpress vitamin receptors on the cell surface. Pantothenic acid (Vit B5) and lipoic acid (or thioctic acid) were covalently linked to methyl pheophorbide (a chlorophyll derivative) and subsequently metallated with zinc and indium. Cell survival assay indicated that the vitamin–chlorin conjugates have better photodynamic activity against the PC-3 prostate cancer line at the nanomolar concentration range than the commercially available starting precursor methyl pheophorbide. Fluorescence and transmission electron microscopy studies indicated some formation of apoptotic cells and cytoplasmic vacuoles of photosensitized prostatic cells. Targeting vitamin receptors in prostatic cancer cells can be utilized to enhance specificity of photosensitizers for photodynamic therapy applications.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Photodynamic Activity of Vitamin–Chlorin Conjugates at Nanomolar Concentrations against Prostate Cancer Cells

Isaac-Lam

Hammonds

2019

ACS Omega

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“…Along with FA and Trf, other endogenous ligands have been investigated for anticancer targeted-PDT. For instance, biotin receptors have been shown to be more overexpressed than FRα in several cancer cell lines of different histological origin (e.g., colon, breast, renal, lung and leukemia) [ 168 ]. Biotin-targeted PSs were demonstrated to promote specific and enhanced accumulation in cancer cells, which was correlated with improved phototoxicity compared to what was obtained with free forms [ 168 , 169 , 170 , 171 ].…”

Section: Ligand-targeted Photosensitizersmentioning

confidence: 99%

“…For instance, biotin receptors have been shown to be more overexpressed than FRα in several cancer cell lines of different histological origin (e.g., colon, breast, renal, lung and leukemia) [ 168 ]. Biotin-targeted PSs were demonstrated to promote specific and enhanced accumulation in cancer cells, which was correlated with improved phototoxicity compared to what was obtained with free forms [ 168 , 169 , 170 , 171 ]. The synthesis of steroid-targeted PS is also a relatively common strategy, especially when targeting hormone-dependent tumors such as breast or ovarian cancers [ 172 , 173 , 174 ].…”

Section: Ligand-targeted Photosensitizersmentioning

confidence: 99%

Ligand-Targeted Delivery of Photosensitizers for Cancer Treatment

et al. 2020

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Photodynamic therapy (PDT) is a promising cancer treatment which involves a photosensitizer (PS), light at a specific wavelength for PS activation and oxygen, which combine to elicit cell death. While the illumination required to activate a PS imparts a certain amount of selectivity to PDT treatments, poor tumor accumulation and cell internalization are still inherent properties of most intravenously administered PSs. As a result, common consequences of PDT include skin photosensitivity. To overcome the mentioned issues, PSs may be tailored to specifically target overexpressed biomarkers of tumors. This active targeting can be achieved by direct conjugation of the PS to a ligand with enhanced affinity for a target overexpressed on cancer cells and/or other cells of the tumor microenvironment. Alternatively, PSs may be incorporated into ligand-targeted nanocarriers, which may also encompass multi-functionalities, including diagnosis and therapy. In this review, we highlight the major advances in active targeting of PSs, either by means of ligand-derived bioconjugates or by exploiting ligand-targeting nanocarriers.

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“…The valeric acid moiety enables biotin to participate in various syntheses [ 16 ]. A few PSs, like methyl-pheophorbide and phthalocyanine, have been conjugated to biotin and showed improved therapeutic efficacy to biotin-receptor- (BR) positive cancer cells [ 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

Chlorin e6-Biotin Conjugates for Tumor-Targeting Photodynamic Therapy

Liu

Jin

et al. 2021

Molecules

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To improve the tumor-targeting efficacy of photodynamic therapy, biotin was conjugated with chlorin e6 to develop a new tumor-targeting photosensitizer, Ce6-biotin. The Ce6-biotin had good water solubility and low aggregation. The singlet-oxygen generation rate of Ce6-biotin was slightly increased compared to Ce6. Flow cytometry and confocal laser scanning microscopy results confirmed Ce6-biotin had higher binding affinity toward biotin-receptor-positive HeLa human cervical carcinoma cells than its precursor, Ce6. Due to the BR-targeting ability of Ce6-biotin, it exhibited stronger cytotoxicity to HeLa cells upon laser irradiation. The IC50 against HeLa cells of Ce6-biotin and Ce6 were 1.28 µM and 2.31 µM, respectively. Furthermore, both Ce6-biotin and Ce6 showed minimal dark toxicity. The selectively enhanced therapeutic efficacy and low dark toxicity suggest that Ce6-biotin is a promising PS for BR-positive-tumor-targeting photodynamic therapy.

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Biotinylated Chlorin and Its Zinc and Indium Complexes: Synthesis and In Vitro Biological Evaluation for Photodynamic Therapy

Cited by 21 publications

References 42 publications

Synthesis and Photodynamic Activity of Vitamin–Chlorin Conjugates at Nanomolar Concentrations against Prostate Cancer Cells

Synthesis and Photodynamic Activity of Vitamin–Chlorin Conjugates at Nanomolar Concentrations against Prostate Cancer Cells

Ligand-Targeted Delivery of Photosensitizers for Cancer Treatment

Chlorin e6-Biotin Conjugates for Tumor-Targeting Photodynamic Therapy

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