Review
Chemistry, Multidisciplinary
Shunzhe Zheng, Guanting Li, Jianbin Shi, Xinying Liu, Meng Li, Zhonggui He, Chutong Tian, Ken-ichiro Kamei
Summary: Due to the severe dose-dependent toxicity and drug resistance, platinum (Pt)-based chemotherapy has limitations. Pt(IV) prodrug nanotherapeutics have emerged as a promising approach to improve the antitumor performance of Pt drugs. This article summarizes the latest advances in Pt(IV) prodrug nano-therapeutics, including their potential for overcoming biological barriers and their synergistic effects with other therapies.
JOURNAL OF CONTROLLED RELEASE
(2023)
Article
Chemistry, Multidisciplinary
Joao Pedro A. Souza, Leociley R. A. Menezes, Francielle P. Garcia, Debora B. Scariot, Pamela T. Bandeira, Mateus B. Bespalhok, Siddhartha O. K. Giese, David L. Hughes, Celso Nakamura, Andersson Barison, Alfredo R. M. Oliveira, Renan B. Campos, Leandro Piovan
Summary: A series of multi-ring organotelluranes containing a Te-O bond were synthesized and characterized, with theoretical calculations elucidating the oxidation-cyclization mechanism involved in the formation of heterocycles. Anti-diastereoisomers were identified as major products for compounds with two chirality centers. Antileishmanial assays revealed that three compounds exhibited higher activity and selectivity than the reference, with stability studies showing no structural modifications in different media or temperatures up to 65 degrees C.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Lukas A. Wolzak, Joen J. Hermans, Folkert de Vries, Keimpe J. van den Berg, Joost N. H. Reek, Moniek Tromp, Ties J. Korstanje
Summary: Studies found that under catalytically relevant conditions only monomeric n-butyltin(IV) carboxylates and dimeric species are present, while Density Functional Theory calculations support a mononuclear mechanism with carbon-oxygen bond breaking as the rate-determining step.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Review
Chemistry, Inorganic & Nuclear
Zoufeng Xu, Zhigang Wang, Zhiqin Deng, Guangyu Zhu
Summary: Platinum-based anticancer drugs have been widely used in clinical practice for over 40 years, with a focus on developing platinum(IV) prodrugs based on traditional platinum(II) anticancer drugs. Recent progress in the field includes synthesizing platinum(IV) prodrugs with new oxidizing reagents, understanding the hydrolysis and stability of platinum(IV) complexes, and exploring reduction processes to achieve controllable intracellular reduction of platinum(IV) prodrugs. This review aims to enhance researchers' understanding of platinum(IV) anticancer prodrugs and inspire new strategies, ideas, and applications in metal-based drugs.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Inorganic & Nuclear
Ran Zhang, Yueyue Zhang, Liumei Tang, Yixing Xu, Hao Li, Xueping Jiang, Xiangdong Xin, Zhongzheng Gui
Summary: A series of Pt(IV) prodrugs containing a microtubule inhibitor paclitaxel were synthesized and evaluated for their antitumor activity. One of the prodrugs, named Ptxplatin, effectively entered cancer cells and induced DNA damage, cell cycle arrest, and inhibition of cell migration. Furthermore, Ptxplatin caused mitochondrial dysfunction and triggered endoplasmic reticulum stress, ultimately leading to cancer cell death.
INORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Alessandra Barbanente, Valentina Gandin, Chiara Donati, Carmela Ilaria Pierro, Giovanni Natile, Nicola Margiotta
Summary: Platinum-based drugs have been successful in treating solid tumors, but toxicity and resistance limit their outcomes. Natural products, such as 10-HDA found in royal jelly, are being explored as safe and easily available anti-cancer drugs. In this study, the researchers aimed to combine the functionality of 10-HDA with platinum to develop new compounds with potential anti-cancer activity. The synthesized compounds were characterized and tested for their cytotoxicity against human tumor cell lines. The results showed that some of the new compounds exhibited promising activity against specific tumor cell lines.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Qiyuan Zhou, Shu Chen, Zoufeng Xu, Gongyuan Liu, Shuyuan Zhang, Zhigang Wang, Man-Kit Tse, Shek-Man Yiu, Guangyu Zhu
Summary: This study reports the synthesis of Pt-IV complexes bearing axial pyridines through ligand exchange reactions. It was discovered that these axial pyridines can be quickly released after reduction, indicating their potential as axial leaving groups. Two multitargeted Pt-IV prodrugs containing bioactive pyridinyl ligands, a PARP inhibitor and an EGFR tyrosine kinase inhibitor, were successfully obtained using this method. These conjugates show great potential for overcoming drug resistance, with the latter inhibiting the growth of Pt-resistant tumor in vivo. This research expands the synthetic methods for Pt-IV prodrugs and increases the range of bioactive axial ligands that can be conjugated to a Pt-IV center.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Inorganic & Nuclear
Jason C. Crack, Nick E. Le Brun
Summary: Iron-sulfur (FeS) clusters are protein cofactors essential for various biological functions such as electron transfer, catalysis, and gene regulation. Recent progress in using mass spectrometry has provided new insights into FeS cluster assembly and chemistry, particularly in transcriptional regulators coordinating cellular responses to changing conditions.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Inorganic & Nuclear
Violet Eng Yee Lee, Zhi Chiaw Lim, Suet Li Chew, Wee Han Ang
Summary: A common challenge in Pt(IV) prodrug design is the limited repertoire of linkers available to connect the Pt(IV) scaffold with the bioactive payload. This study introduces a new class of Pt(IV) prodrugs using masked self-immolative 4-aminobenzyl linkers for controlled and traceless codrug delivery, which proved to be more effective than traditional methods in vitro.
INORGANIC CHEMISTRY
(2021)
Article
Engineering, Biomedical
Xiaohui Xiao, Yupeng Wang, Jieyao Chen, Peng Qin, Peiyao Chen, Dongfang Zhou, Yue Pan
Summary: This study presents a self-targeting nano-assembly strategy based on platinum(IV)-lactose amphiphilic prodrug for synergistic and safe chemoradiotherapy of hepatocellular carcinoma (HCC). The nano-assembly targets HCC cells and releases cisplatin to induce DNA damage and cell apoptosis. Under X-ray irradiation, the assembly enhances the cell-killing effect of radiotherapy.
Article
Environmental Sciences
Chanat Chokejaroenrat, Chainarong Sakulthaew, Sirimon Chantakulvanich, Athaphon Angkaew, Kanokwan Teingtham, Piyaporn Phansak, Thapanee Poompoung, Daniel D. Snow, Clifford E. Harris, Steve D. Comfort
Summary: The objective of this study was to investigate the efficiency of zinc ferrite nanocomposites (ZnFe2O4) and sulfur-containing reductants (SCR) in co-activating persulfate (PS) and treating herbicide-contaminated water. The results showed that the addition of ZnFe2O4 significantly enhanced the herbicide degradation rates by generating reactive radical species, such as SO4- and OH-. The degradation pathways of atrazine and alachlor were proposed, involving both dehydration and hydroxylation. ZnFe2O4 was found to prolong the oxidative treatment and reduce the impact on soil microcosms and plant growth.
SCIENCE OF THE TOTAL ENVIRONMENT
(2023)
Article
Chemistry, Multidisciplinary
Dachuan Qi, Lei Xing, Lijun Shen, Wenshuang Sun, Cheng Cai, Chunhua Xue, Xuwei Song, Hua Yu, Hulin Jiang, Chengjun Li, Qingri Jin, Zhiqi Zhang
Summary: This study developed a GSH-depleted drug for breast cancer, which can effectively treat breast cancer by increasing oxidative stress and inducing ferroptosis.
CHINESE CHEMICAL LETTERS
(2022)
Article
Medicine, Research & Experimental
Tushar Date, Kaushik Kuche, Rohan Ghadi, Pradeep Kumar, Sanyog Jain
Summary: Cisplatin is an anticancer drug with challenges in drug delivery. Cisplatin(IV) prodrug formation can effectively resolve these challenges. The selection of axial ligands plays a key role in determining the therapeutic outcomes. Rational design of cisplatin(IV) derivatives can improve their stability and cellular uptake, reducing side effects and offering potential in resolving cisplatin drug delivery challenges.
MOLECULAR PHARMACEUTICS
(2022)
Review
Chemistry, Organic
Antony Chipman
Summary: This article provides a detailed introduction to the historical development of ortho-iodoxybenzoic acid (IBX) and the Dess-Martin periodinane (DMP), focusing on the plausible reaction mechanisms of I-V iodoxolone. Through concise discussions of examples sourced from the literature, the relevant structures and electron redistribution processes of these chemical reactions are presented.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Pharmacology & Pharmacy
Theresa Mendrina, Isabella Poetsch, Hemma Schueffl, Dina Baier, Christine Pirker, Alexander Ries, Bernhard K. K. Keppler, Christian R. R. Kowol, Dan Gibson, Michael Grusch, Walter Berger, Petra Heffeter
Summary: Platinum compounds are effective treatment options for various cancer types, but their use is limited by side effects and drug resistance. A new multi-targeted platinum(IV) prodrug, cisPt(PhB)(2), has shown promising anticancer activity and the ability to overcome drug resistance mechanisms. The drug's mode of action is influenced by cellular fatty acid metabolism and mitochondrial activity. Specifically, it is more effective against cisplatin-resistant cancer cells with Warburg-like properties. This orally applicable prodrug has the potential to improve cancer treatment outcomes.
Article
Chemistry, Physical
Mona Jalali, Farshad Shiri, Alex C. Bissember, Brian F. Yates, Alireza Ariafard
Summary: Density functional theory (DFT) was used to investigate the mechanism of the efficient hydroalkylation of styrene with acetylacetone in the presence of a bismuth catalyst. The results show that the mechanism is fundamentally different from the analogous gold-catalyzed reaction and is characterized by bismuth coordinating to the oxygens of acetylacetone to form a chelated complex. The activation energy for the reaction with bismuth via the enol isomer of acetylacetone is much lower compared to the ketone isomer.
Article
Chemistry, Inorganic & Nuclear
Howard Z. Ma, Allan J. Canty, Richard A. J. O'Hair
Summary: A near thermal two-step catalytic cycle for the selective release of hydrogen from formic acid was revealed. Mononuclear copper hydride anions were found to react with formic acid to yield copper formate anions and H-2. The copper formate anions can decarboxylate to reform the copper hydride, thus closing the catalytic cycle.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Jackson S. Henneveld, Farshad Shiri, Alireza Ariafard, Nigel T. Lucas, Alex C. Bissember, Bill C. Hawkins
Summary: The investigation and formalization of the distinctive dipole-transmissive dipolar cycloaddition (DTDC) methodology is reported. A DTDC procedure was developed by taking advantage of the structural complementarity of azide and diazoalkane 1,3-dipoles. This method allows for the rapid construction of functionalized polycyclic N-heterocycles through intramolecular azide-alkene 1,3-dipolar cycloadditions followed by N-derivatization and subsequent 1,3-dipolar cycloadditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Farshad Shiri, Alireza Ariafard
Summary: 1,6-enynes can be cyclized to yield cyclopropyl ketones using PhI(OAc)(2) (PIDA) in the presence of Pd(OAc)(2) as a catalyst. However, when 1,6-enynes are substituted by a hydroxy group at the alpha-position, polycyclic oxa-heterocycles are formed instead. This study aims to investigate the mechanistic aspects of these transformations and reveals that the change in chemoselectivity is due to the electronic nature of the Pd catalyst changing from pi-philicity to oxophilicity during the catalytic cycle.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Alex C. Bissember, Angus Olding, Curtis C. Ho, Nigel T. Lucas, Allan J. Canty
Summary: By covalently tethering a supporting ligand to a boron nucleophile, typically elusive and kinetically unstable Suzuki-Miyaura (SM) pretransmetalation species were able to be controlled. This strategy allowed for the synthesis of an organonickel(II) boronate pretransmetalation intermediate and its characterization through X-ray crystallography. Performing reactions in the presence of carbon monoxide led to pretransmetalation intermediates in carbon-ylative SM reactions-aroylmetal boronates, enabling the determination of the X-ray crystal structures of an aroylnickel(II) boronate (and an aroylpalladium(II) boronate).
Article
Chemistry, Applied
Janina Bucher, Thomas Wurm, Kaveh Farshadfar, Michael Schukin, Georgios Uzunidis, Matthias Rudolph, Frank Rominger, Alireza Ariafard, A. Stephen K. Hashmi
Summary: By using the sterically highly demanding steering ligand IPr* on a gold(I) center, a 6-endo-dig cyclization pathway can be induced in 1,5-diynes with terminal alkyne moieties. The resulting aurated naphthyl cations are utilized for intermolecular C-C bond formation through C-H insertion of aromatic and aliphatic C-H bonds. The mechanisms of these transformations were studied through quantum chemical calculations.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Mohammad Rezaei-Gohar, Kamran Amiri, Kimia Aghaie, Behrouz Nayebzadeh, Alireza Ariafard, Farshad Shiri, Frank Rominger, Dmitry Dar'in, Mikhail Krasavin, Saeed Balalaie
Summary: An efficient procedure for accessing a wide variety of interconnected imidazo[1,2-a]pyridine and benzimidazole skeletons through the C-N bond using a new type of Buchwald-Hartwig reaction is described. Furthermore, changing the equivalent ratio of starting materials allows for the synthesis of bis(imidazo[1,2-a]pyridin-3-yl)aryl-1,2-diamine scaffolds. The protocol offers several advantages, including the formation of four new bonds (C=C, C-N), a transition-metal-free reaction, a broad substrate scope, high yields, and mild reaction conditions. The reaction mechanism is confirmed by DFT calculations.
Article
Chemistry, Inorganic & Nuclear
Allan J. J. Canty, Alireza Ariafard
Summary: Density functional theory was employed to study the mechanistic of the oxidation of pincer complex Pd-II(mer-NCN)(K-1-O2CPh) by diphenyliodine(III) triflate in the presence of bicarbonate base. The results suggest that concerted oxidative addition by Ph2I(OCO2H) is favored over a Ph+ transfer mechanism to initially form octahedral PhPdIV(mer-NCN)(K-1-O2CPh){I(Ph)(& BULL;& BULL;& BULL;OCO2H)-I}. Interaction of bicarbonate with the iodine center has little impact on the concerted transition state but disrupts the Ph+ transfer mechanism.
Article
Multidisciplinary Sciences
Lina Song, Xianhai Tian, Kaveh Farshadfar, Farshad Shiri, Frank Rominger, Alireza Ariafard, A. Stephen K. Hashmi
Summary: Here, the authors developed a metal-free, visible light-mediated cascade reaction for the preparation of azepinone derivatives. The reaction involves a photochemical generation of 2-aryloxyaryl nitrene, [2 + 1] annulation, ring expansion/water addition cascade reaction without using any metal catalyst. The reaction shows broad scope and the obtained products can undergo divergent transformations to afford other related compounds. A computational study suggests a pathway involving a step-wise aziridine formation, followed by a ring-expansion to the seven-membered heterocycle. Finally, water is added in a regio-selective manner, accelerated by the added TsOH. Photochemical nitrene transfer offers a green avenue for heterocyclic syntheses.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Yang Yang, Allan J. Canty, Richard A. J. O'Hair
Summary: Multistage mass spectrometry (MSn) experiments were conducted to investigate the extrusion-insertion reactions of a palladium complex. The results showed that the organopalladium cation was formed and reacted with phenylmethylketene to produce an enolate. Further analysis revealed the formation of an acyl complex. However, attempts to develop a palladium-mediated one-pot synthesis of ketones proved challenging due to low yields and side product formation.
AUSTRALIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Nusaybah Alotaibi, Rasool Babaahmadi, Milan Pramanik, Tanja Kaehler, Ayan Dasgupta, Emma Richards, Alireza Ariafard, Thomas Wirth, Rebecca L. L. Melen
Summary: In this study, the C3-allylation of indoles using allylic esters was achieved using B(3,4,5-F3H2C6)(3) as the catalyst. A total of 25 examples of C3-allylated products were obtained with yields up to 97%. The mechanism of the reaction was investigated through detailed Density Functional Theory (DFT) studies.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Farshad Shiri, Alireza Ariafard
Summary: This study demonstrates that the oxidative addition of hypervalent iodine PhICl2 to Au(I) complexes LAuAr follows an unprecedented stepwise mechanism. The energy of the Au(I) d(x2-y2) orbital determines the ease of the oxidative addition reaction; the fewer electron-withdrawing substituents present on the Ar ligand, the higher the energy of the d(x2)-(y2) orbital and the easier the oxidative addition.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Farshad Shiri, Curtis C. Ho, Alex C. Bissember, Alireza Ariafard
Summary: This study investigates the reaction between gold(I) complexes and hypervalent iodine(III) reagents and uncovers a transmetalation mechanism between gold(I) and gold(III) complexes. It establishes a theoretical model that can predict the outcomes of reactions involving these complexes, providing a foundation for advancements in this field.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Inorganic & Nuclear
Howard Z. Ma, Allan J. Canty, Richard A. J. O'Hair
Summary: This study investigates the possibility of selective decarbonylation of formic acid mediated by molybdate anions in a formal catalytic cycle. The results show that dimolybdate anions can effectively catalyze the decomposition of formic acid, yielding carbon monoxide and water.
DALTON TRANSACTIONS
(2023)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
