Mannose-conjugated platinum complexes reveals effective tumor targeting mediated by glucose transporter 1

Liu, Ran; Li, Hong; Gao, Xiangqian; Mi, Qian; Zhao, Hongxia; Gao, Qingzhi

doi:10.1016/j.bbrc.2017.04.004

Cited by 33 publications

(24 citation statements)

References 20 publications

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“…[113,127] An ester linkage was coupled to the C7 or C10 hydroxy group of taxoidsw ith av ariety of w-glycosyloxycarboxylic acids (n = 0-8, 35)t of orm an array of glycosylatedp aclitaxel and docetaxel derivatives (Figures 6, 7, and Ta ble 1). [68,128] In accordancew ith other research results, after glycosylation, the aqueous solubility of those taxoid derivatives significantly increased. Among them, mannose-taxoid conjugate 29 was highest, while glucose-taxoid 27 was lowest, with 258-and 58-fold that of paclitaxel (25)i tself.…”

Section: Sugar Typesupporting

confidence: 89%

“…An ester linkage was coupled to the C7 or C10 hydroxy group of taxoids with a variety of ω‐glycosyloxycarboxylic acids ( n =0–8, 35 ) to form an array of glycosylated paclitaxel and docetaxel derivatives (Figures , , and Table ) . In accordance with other research results, after glycosylation, the aqueous solubility of those taxoid derivatives significantly increased.…”

Section: Structure–activity Relationshipssupporting

confidence: 82%

“…[128] The in vitro cytotoxicities of all glycosylated paclitaxel derivatives (27-30)a gainst P388 leukemia cells werei nferiort ot hat of the lead paclitaxel (25), but the glycosylatedd ocetaxel analogues were found to be more cytotoxic than their parent docetaxel ( 26), with the exception of the mannose derivative. [68,128] As for in vivo antitumor activities, on the whole, the tendency of cytotoxicity of all the glycosylated taxoid derivatives (27-34)d ecreased. It is worth noting that galactose-bound taxoids 28 and 32 had advantages over glucose-bound (27, 31)a nd mannose-bound (29, 33)t axoidsi nt he inhibition of tumor growth.…”

Section: Sugar Typementioning

confidence: 95%

“…Among them, mannose–taxoid conjugate 29 was highest, while glucose–taxoid 27 was lowest, with 258‐ and 58‐fold that of paclitaxel ( 25 ) itself . The in vitro cytotoxicities of all glycosylated paclitaxel derivatives ( 27 – 30 ) against P388 leukemia cells were inferior to that of the lead paclitaxel ( 25 ), but the glycosylated docetaxel analogues were found to be more cytotoxic than their parent docetaxel ( 26 ), with the exception of the mannose derivative . As for in vivo antitumor activities, on the whole, the tendency of cytotoxicity of all the glycosylated taxoid derivatives ( 27 – 34 ) decreased.…”

Section: Structure–activity Relationshipsmentioning

confidence: 99%

“…The antitumor activity and aqueous solubility of the a-galactose-bound taxoid 32 a were superior to those of the corresponding b-galactose derivative 32 b.I nc ontrast, the aqueous solubility of a-glucosebound taxoid 31 a was highert han that of the b-glucoseboundt axoid 31 b,b ut its antitumora ctivity. [128] Also, when substituted at the C9, C5, and C2 positions of sialic acid, the tendency of their binding affinity for the receptors, on the whole, had been documented to substantially increase. [18] In contrastt os ialic acid with b-linked configuration, the corresponding a-linkage to threonine exhibitedi ncreased potency by more than 100-fold.…”

Section: A-anomer Versus B-anomermentioning

confidence: 99%

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Application of Mono‐ and Disaccharides in Drug Targeting and Efficacy

Yuan

Chen

et al. 2018

ChemMedChem

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Carbohydrates and their conjugates play important roles in many biological processes including fertilization, differentiation, development, immune response, and infection. Their activities are largely dependent on the properties of terminal mono- or disaccharides. Galactose, mannose, fucose, glucose, sialic acid, etc., are commonly used as powerful scaffolds installed on drug molecules for targeting specific tissues including brain, liver, and cancers, and as epitopes for enhancing the targeting of various vaccines. This review focuses on the influence of their structural variations, including changes in sugar type, substituent groups and their positions, as well as length of linker portion, on the targeting of drugs or their efficacy. Particular attention is paid to the targeting properties of mono- and disaccharides applied in drug design and discovery.

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Section: Sugar Typesupporting

confidence: 89%

Section: Structure–activity Relationshipssupporting

confidence: 82%

Section: Sugar Typementioning

confidence: 95%

Section: Structure–activity Relationshipsmentioning

confidence: 99%

Section: A-anomer Versus B-anomermentioning

confidence: 99%

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Application of Mono‐ and Disaccharides in Drug Targeting and Efficacy

Yuan

Chen

et al. 2018

ChemMedChem

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An Unrevealed Molecular Function of Corannulene Buckybowl Glycoconjugates in Selective Tumor Annihilation by Targeting the Cancer‐Specific Warburg Effect

et al. 2022

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The biomedical application of corannulene 𝝅-bowls is historically limited by low solubility and bioavailability despite the potential in their unique electronic properties for new functional materials. Herein, the unexpected role and molecular mechanism of Corranulene 𝝅-bowls are uncovered in biomedical applications as an effective anticancer agent for Warburg effect mediated selective tumor targeting. The corannulene triazolyl monosaccharides Cor-sugars exhibit highly potent cytotoxicity against human cancer cells and effectively inhibit xenograft growth of hyperglycolytic tumors. Particularly, the galactose-conjugated Cor-gal exhibits superior in vivo anticancer efficacy in A549 tumor models with outstanding safety profile compared to doxorubicin. Moreover, the combined treatment of Cor-gal with immune checkpoint inhibitor results in an effective synergy in treating H460 human lung carcinoma. An uptake mechanism study reveals that Cor-sugars exploit tumor-specific glucose transporter glucose transporter 1 (GLUT1) for targeted cell delivery and intra-tumoral accumulation through the cancer-specific Warburg effect. Their significant anticancer activity is attributed to multiphasic DNA-binding and cell cycle alteration effects. This study uncovers new molecular properties of corannulene buckybowl and enabling their potential new applications in biomedical engineering.

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Glycoconjugated Metal Complexes as Cancer Diagnostic and Therapeutic Agents

et al. 2020

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The possibility of selectively delivering metal complexes to a defined cohort of cells on the basis of their metabolic features is a highly challenging goal, which may be extremely useful for a series of purposes, including diagnosis and therapy of pathological states, such as cancer. Tumor cells display augmented requests for carbohydrates and, in particular, for glucose in order to sustain their high proliferation rate, which causes an increased glycolytic process (Warburg effect). Since several metal complexes display diagnostic and/or therapeutic properties, their conjugation to carbohydrate portions often induce their preferential accumulation in cancer cells, similarly to what is observed with fluorodeoxyglucose (FDG). In this review we have considered the latest developments of glycoconjugates containing metal complexes in their structures. These compounds are classified as diagnostic or therapeutic agents and are further systematically discussed on the basis of the metal atom they contain. Several diagnostic techniques are possible with these probes, since, depending on the metal species included in their structures, they may be employed in nuclear medicine (PET, SPECT), magnetic resonance imaging, luminescence and phosphorescence. At the same time, the lack of selective cytotoxicity displayed by several metal‐based chemotherapeutic agents, may also be solved by the conjugation of these agents to carbohydrate portions. Overall, data so far available reveal the great potential of this chemical class in the early detection and in the cure of severe neoplastic diseases, which still needs to be fully explored in the clinic.

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Mannose-conjugated platinum complexes reveals effective tumor targeting mediated by glucose transporter 1

Cited by 33 publications

References 20 publications

Application of Mono‐ and Disaccharides in Drug Targeting and Efficacy

Application of Mono‐ and Disaccharides in Drug Targeting and Efficacy

An Unrevealed Molecular Function of Corannulene Buckybowl Glycoconjugates in Selective Tumor Annihilation by Targeting the Cancer‐Specific Warburg Effect

Glycoconjugated Metal Complexes as Cancer Diagnostic and Therapeutic Agents

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