Development of a series of flurbiprofen and zaltoprofen platinum(<scp>iv</scp>) complexes with anti-metastasis competence targeting COX-2, PD-L1 and DNA

Li, Zuojie; Li, Linming; Zhao, Wenhuan; Sun, Bin; Liu, Zhifang; Liu, Min; Han, Jun; Wang, Zhengping; Li, Dacheng; Wang, Qingpeng

doi:10.1039/d2dt00944g

Cited by 22 publications

(18 citation statements)

References 49 publications

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“…Yield: 0.23 g (45%). NMR spectroscopic data is as reported [31] and is included in the Supporting Information. HRMS (ESI) m/z: [Oxa(AcFA) 2 ]: Light yellow powder.…”

Section: Methodsmentioning

confidence: 99%

“…In these regards, numerous combinations of anti-inflammatory agents with platinum drugs have been reported over the years where different nonsteroidal anti-inflammatory drugs (NSAIDs) or other compounds with inflammation reducing properties have been exploited. [22][23][24][25][26][27][28][29][30][31][32][33][34][35][36] A century after Paul Ehrlich first coined the term "magic bullet" referring to an antigen's exceptional capacity to target specific "side chains" on the surface of cells, this concept of a site-specific targeting has become of crucial importance in the field of cancer treatment. [37] With the emergence of nanotechnology, fascinating advances have been made toward the development of systems following this concept.…”

Section: Introductionmentioning

confidence: 99%

“…In these regards, numerous combinations of anti‐inflammatory agents with platinum drugs have been reported over the years where different nonsteroidal anti‐inflammatory drugs (NSAIDs) or other compounds with inflammation reducing properties have been exploited. [ 22–36 ]…”

Section: Introductionmentioning

confidence: 99%

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SBA‐15 Particles as Carriers for a Series of Platinum(IV) Complexes with Oxaliplatin Scaffolds Bearing Different Anti‐Inflammatory Drugs: Promising Strategy Against Breast Cancer

Predarska

Saoud

Cepus

et al. 2023

Advanced Therapeutics

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Oxaliplatin is a third‐generation platinum(II)‐based drug mainly utilized to treat colon cancer, as part of a combinatory regime. Aiming to expand the knowledge on the effects of oxaliplatin and its derivatives on different tumor types, oxaliplatin‐based platinum(IV) platforms are designed and prepared to assess their antitumor capacity against various breast cancer cell lines. In the two axial positions of the platinum(IV) system, different inflammation reducing agents, non‐steroidal anti‐inflammatory drugs (fenoprofen, flurbiprofen, both as racemates) and phenolic acids (acetyl‐protected and unprotected ferulic acid, cinnamic acid) are incorporated as anionic ligands. The prepared platinum(IV) hybrids are loaded with great encapsulation efficiency into mesoporous SBA‐15 material to serve as drug delivery vehicle, and the obtained nanostructured material can ensure very slow drug release beneficial for prolonged circulation in vivo and passive targeting. Both, free and in SBA‐15 immobilized platinum(IV) complexes with oxaliplatin core, displayed potent antitumor activity in four breast cancer cell lines (MCF‐7, BT‐474, HCC1937 and MDA‐MB‐468), showing great prospect in overcoming oxaliplatin and cisplatin resistance. Mechanistic investigations in MDA‐MB‐468 cells of oxaliplatin and its fenoprofen derivative as the most active representative of the prepared complexes showed that the decreased cell viability resides in activation of apoptotic mechanisms.

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“…Yield: 0.23 g (45%). NMR spectroscopic data is as reported [31] and is included in the Supporting Information. HRMS (ESI) m/z: [Oxa(AcFA) 2 ]: Light yellow powder.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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SBA‐15 Particles as Carriers for a Series of Platinum(IV) Complexes with Oxaliplatin Scaffolds Bearing Different Anti‐Inflammatory Drugs: Promising Strategy Against Breast Cancer

Predarska

Saoud

Cepus

et al. 2023

Advanced Therapeutics

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“…[47] Tumor metastasis plays an essential role in cancer evolution and is also one of the major reasons for the failure of advanced tumor therapy. [48,49] Herein, the inhibition effects of complex 1 on adherent cell migration were detected by wound-healing assay. As shown in [Figure 10], after 24 h of incubation with the concentration of 0.25 Â IC 50 , the wound closure ratios [WCR = (R 0 -R 1 )/R 0 Â 100%] for the treated group and control group were 5.85% and 15.43%, respectively.…”

Section: Antimetastatic Properties Of Complex 1 On Hepg-2 Cellsmentioning

confidence: 99%

Syntheses, structures, and the in vitro anticancer mechanism of triorganotin (IV) complexes based on 4,4′‐stilbenedicarboxylic acid

et al. 2023

Applied Organom Chemis

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Five triorganotin (IV) complexes, [(Ph3Sn)2L] (1) [(Me3Sn)2L]n (2), [(n‐Bu3Sn)2L]n (3), [(n‐Bu 3Sn)2L(4,4′‐bpy)]n (4), [(n‐Bu3Sn)2L(bpe)]n (5) [H2L = 4,4′‐stilbenedicarboxylic acid, 4,4′‐bpy = 4,4′‐bipyridine, bpe = 4,4′‐vinylenedipyridine], were successfully prepared and structurally characterized by FT‐IR, elemental analysis, NMR spectroscopy, PXRD, and X‐ray crystallography. Complex 1 is a monomer containing two tin atoms, and 1D infinite chains can be formed between the monomers through CH···π interactions. Complexes 2 and 3 represent 2D network structures containing tetranuclear 38‐membered rings. Meanwhile, complexes 4 and 5 are 1D chain‐like structures and form the 2D network and 3D stereo structure via CH···O intermolecular interactions, respectively. The anticancer activities of the complexes were investigated against different cancer cells (A549, HeLa, and HepG‐2). Complexes 1 and 3–5 showed superior anticancer activity. Meanwhile, the anticancer mechanism of complex 1 was studied with the results that complex 1 can promote the production of excessive reactive oxygen species, induce mitochondrial membrane permeability depolarization, and release proapoptotic factors from mitochondria into the cytosol, followed by caspase‐3 activation, nuclei damage, and apoptosis. Excitingly, complex 1 also has good antimetastatic ability toward HepG‐2 cancer cells.

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“…Inspired by these observations and as a continuation of our work in developing novel platinum antitumor agents, , here, CLQ as a promising autophagy activator was conjugated with the platinum(IV) system to produce a series of CLQ platinum(IV) complexes 1–7 as potential antiproliferative and antimetastatic agents (Figure ). To explore the influence of platinum core onto the antitumor performance, complexes 1–3 with CDDP, OLP, and CBP cores were designed.…”

Section: Introductionmentioning

confidence: 99%

Development of Clioquinol Platinum(IV) Conjugates as Autophagy-Targeted Antimetastatic Agents

Zhang

et al. 2023

J. Med. Chem.

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A series of autophagy-targeted antimetastatic clioquinol (CLQ) platinum(IV) conjugates were designed and prepared by incorporating an autophagy activator CLQ into the platinum(IV) system. Complex 5 with the cisplatin core bearing dual CLQ ligands with potent antitumor properties was screened out as a candidate. More importantly, it displayed potent antimetastatic properties both in vitro and in vivo as expected. Mechanism investigation manifested that complex 5 induced serious DNA damage to increase γ-H2AX and P53 expression and caused mitochondria-mediated apoptosis through the Bcl-2/Bax/caspase3 pathway. Then, it promoted prodeath autophagy by suppressing PI3K/AKT/mTOR signaling and activating the HIF-1α/ Beclin1 pathway. The T-cell immunity was elevated by restraining the PD-L1 expression and subsequently increasing CD3 + and CD8 + T cells. Ultimately, metastasis of tumor cells was suppressed by the synergistic effects of DNA damage, autophagy promotion, and immune activation aroused by CLQ platinum(IV) complexes. Key proteins VEGFA, MMP-9, and CD34 tightly associated with angiogenesis and metastasis were downregulated.

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Development of a series of flurbiprofen and zaltoprofen platinum(iv) complexes with anti-metastasis competence targeting COX-2, PD-L1 and DNA

Abstract: To develop new anti-metastasis chemotherapeutic drugs, a series of flurbiprofen (FLP) and zaltoprofen (ZTP) platinum(IV) complexes targeting COX-2, PD-L1 and DNA were prepared and investigated. Complex 2 with dual FLP...

Cited by 22 publications

References 49 publications

SBA‐15 Particles as Carriers for a Series of Platinum(IV) Complexes with Oxaliplatin Scaffolds Bearing Different Anti‐Inflammatory Drugs: Promising Strategy Against Breast Cancer

SBA‐15 Particles as Carriers for a Series of Platinum(IV) Complexes with Oxaliplatin Scaffolds Bearing Different Anti‐Inflammatory Drugs: Promising Strategy Against Breast Cancer

Syntheses, structures, and the in vitro anticancer mechanism of triorganotin (IV) complexes based on 4,4′‐stilbenedicarboxylic acid

Development of Clioquinol Platinum(IV) Conjugates as Autophagy-Targeted Antimetastatic Agents

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