4.7 Article Proceedings Paper

Synthesis and in vitro anti-tumor activity of carboranyl levodopa

Journal

BIOORGANIC CHEMISTRY
Volume 90, Issue -, Pages -

Publisher

ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.bioorg.2019.103090

Keywords

Neutron capture therapy (NCT); Anti-tumor; Levodopa; Drug delivery; Bio-assessment

Funding

  1. FDCT grant from the Science and Technology Development Fund of Macau [0030/2018/A1]

Ask authors/readers for more resources

Reactions of closo-1-Me-2-Iodobutyl-1,2-closo-dicarborane, 1-Me-2-I(CH2)(4)-C2B10H10, with L-dopa methyl ester can produce carboranyl L-dopa methyl esters in 54% yield in the presence of sodium hydroxide. The appended closo-carboranes can be decapitated with sodium hydroxide in a mixed solvent of ethanol and deionized water to produce highly water-soluble carboranyl levodopa in 64% yield. All the new compounds were characterized by H-1, C-13, B-11 NMR, FT-IR spectroscopy and elemental analysis. The highly water soluble carboranyl levodopa 4 shows promising efficacy of anti-tumors in vitro in the presence of slow neutron beams.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Chemistry, Analytical

Rapid and sensitive colorimetric sensing of the insecticide pymetrozine using melamine-modified gold nanoparticles

Jing-yan Kang, Yu-jie Zhang, Xing Li, Chen Dong, Hong-yu Liu, Li-jing Miao, Paul J. Low, Zhi-xian Gao, Narayan S. Hosmane, Ai-guo Wu

ANALYTICAL METHODS (2018)

Article Chemistry, Multidisciplinary

Cancer cell detection and imaging: MRI-SERS bimodal splat-shaped Fe3O4/Au nanocomposites

Xinmei Zhao, Leyong Zeng, Narayan Hosmane, Yan Gong, Aiguo Wu

CHINESE CHEMICAL LETTERS (2019)

Review Chemistry, Inorganic & Nuclear

Boron-enriched advanced energy materials

Yinghuai Zhu, Shanmin Gao, Narayan S. Hosmane

INORGANICA CHIMICA ACTA (2018)

Article Chemistry, Inorganic & Nuclear

Catalytic conversion of vanillic acid to catechol by palladium acetate/bis(aminomethyl)-nido-dicarba-undecaborane (11) system

Yinghuai Zhu, Zhiyu Bai, Wen Chuen Phuan, Fatima Abi Ghaida, Narayan S. Hosmane, Jun Ding

JOURNAL OF ORGANOMETALLIC CHEMISTRY (2018)

Article Materials Science, Biomaterials

Gadolinium borate and iron oxide bioconjugates: Nanocomposites of next generation with multifunctional applications

Okan Icten, Dursun Ali Kose, Stephan J. Matissek, Jason A. Misurelli, Sherine F. Elsawa, Narayan S. Hosmane, Birgul Zumreoglu-Karan

MATERIALS SCIENCE AND ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS (2018)

Article Chemistry, Multidisciplinary

Nanostructured boron compounds for cancer therapy

Yinghuai Zhu, Narayan S. Hosmane

PURE AND APPLIED CHEMISTRY (2018)

Article Chemistry, Medicinal

Carborane-Containing Matrix Metalloprotease (MMP) Ligands as Candidates for Boron Neutron-Capture Therapy (BNCT)

Marlon R. Lutz, Sebastian Flieger, Andre Colorina, John Wozny, Narayan S. Hosmane, Daniel P. Becker

CHEMMEDCHEM (2020)

Article Chemistry, Multidisciplinary

Functionalized Boron Nanoparticles as Potential Promising Antimalarial Agents

Yinghuai Zhu, Parichat Prommana, Narayan S. Hosmane, Paolo Coghi, Chairat Uthaipibull, Yingjun Zhang

Summary: Boron nanoparticles with hydroxyl groups were synthesized in situ and characterized using various analytical techniques. These nanoparticles exhibited good antimalarial activity against Plasmodium falciparum, while showing low toxicity to various cell lines.

ACS OMEGA (2022)

Review Biochemistry & Molecular Biology

Boron Chemicals in Drug Discovery and Development: Synthesis and Medicinal Perspective

Bhaskar C. Das, Nitesh K. Nandwana, Sasmita Das, Varsha Nandwana, Mohammed Adil Shareef, Yogarupa Das, Mariko Saito, Louis M. Weiss, Frankis Almaguel, Narayan S. Hosmane, Todd Evans

Summary: This review introduces current boron-containing drug candidates, including boron-based compounds for the treatment of different diseases. It also describes their synthesis, structure-activity relationship, and associated biological activities.

MOLECULES (2022)

Article Biochemistry & Molecular Biology

Self-Assembled Monolayer of Monomercaptoundecahydro-closo-dodecaborate on a Polycrystalline Gold Surface

Martha L. Jimenez-Gonzalez, Juan Pablo F. Rebolledo-Chavez, Marisela Cruz-Ramirez, Rene Antano, Angel Mendoza, Narayan S. Hosmane, Lena Ruiz-Azuara, Jose Luis Hernandez-Lopez, Luis Ortiz-Frade

Summary: In this work, an electrochemical study of the Boron cage monomercaptoundecahydro-closo-dodecaborate [B12H11SH](2-) in solution and in a self-assembled monolayer over a gold electrode was conducted. The study revealed the interaction between the boron cage and the gold surface, formation of a self-assembled monolayer, and the reduction of active sites on the gold surface due to the presence of the boron cage. Bulkier thiols were found to enhance charge accumulation at the electrode-solution interface.

MOLECULES (2022)

Review Biochemistry & Molecular Biology

The Role of Microbiome in Brain Development and Neurodegenerative Diseases

Varsha Nandwana, Nitesh K. Nandwana, Yogarupa Das, Mariko Saito, Tanisha Panda, Sasmita Das, Frankis Almaguel, Narayan S. Hosmane, Bhaskar C. Das

Summary: This review article summarizes the importance of gut microbiota in neurodevelopment and neurodegenerative disorders and discusses breakthroughs in using probiotics, prebiotics, and synbiotics for treating neurological illnesses. It also explores the role of a boron-based diet in memory and neurodegenerative diseases.

MOLECULES (2022)

Article Biochemistry & Molecular Biology

Carborane-Containing Hydroxamate MMP Ligands for the Treatment of Tumors Using Boron Neutron Capture Therapy (BNCT): Efficacy without Tumor Cell Entry

Sebastian Flieger, Mao Takagaki, Natsuko Kondo, Marlon R. Lutz, Yash Gupta, Hiroki Ueda, Yoshinori Sakurai, Graham Moran, Prakasha Kempaiah, Narayan Hosmane, Minoru Suzuki, Daniel P. Becker

Summary: New carborane-bearing hydroxamate matrix metalloproteinase (MMP) ligands with nanomolar potency against MMP-2, -9 and -13 have been synthesized for boron neutron capture therapy (BNCT). In vitro studies showed that these new MMP ligands had high tumoricidal effects in the BNCT assay. This study highlights the importance of targeting MMP enzymes overexpressed on the surface of tumor cells for BNCT efficacy.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2023)

Article Chemistry, Multidisciplinary

Carboxyboranylamino ethanol: unprecedented discovery of boron agents for neutron capture therapy in cancer treatment

Yinghuai Zhu, Jianghong Cai, Narayan S. Hosmane, Minoru Suzuki, Kazuko Uno, Yingjun Zhang, Mao Takagaki

Summary: Carboxyboranylamino ethanol was prepared with a 75.0% yield through an amine-exchange reaction. It showed lower cytotoxicity and higher anti-tumor efficacy in vitro compared to 4-borono-l-phenylalanine (BPA) and methyl 2-hydroxyl-5-(1'-ortho-carbonylmethyl-1',2',3'-triazol-4'-yl)-benzonate (2). The bio-enhancement was explained using molecular docking calculations.

CHEMICAL COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Suppression of the environmental risks of lead in cropland soil using biomass ash and its modified product+

Hongyu Liu, Zhuangwei Zhou, Yujie Zhang, Ningyi Chen, Jingyan Kang, Guijian Liu, Narayan S. Hosmane, Aiguo Wu

NANOSCALE ADVANCES (2019)

Correction Biochemistry & Molecular Biology

LC/HRESI-MS/MS screening, phytochemical characterization, and in vitro antioxidant and cytotoxic potential of Jatropha integerrima Jacq. extracts (vol 140, 106825, 2023)

Mohamed Marzouk, Shimaa M. Khalifa, Amal H. Ahmed, Ahmed M. Metwaly, Hala Sh. Mohammed, Hanan A. A. Taie

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Integration of biophysical and biological approaches to validate fragment-like compounds targeting L,D-transpeptidases from Mycobacterium tuberculosis

Gerardo Andres Libreros-Zuniga, Danilo Pava e Pavao, Vinicius de Morais Barroso, Nathalya Cristina de Moraes Roso Mesquita, Saulo Fehelberg Pinto Braga, Glaucius Oliva, Rafaela Salgado Ferreira, Kelly Ishida, Marcio Vinicius Bertacine Dias

Summary: Tuberculosis is a major global cause of death, and the emergence of drug-resistant strains has increased the burden of this disease. New alternative therapies are constantly needed, and recent research has identified small molecules as potential inhibitors of Ldts in M. tuberculosis, which have antimycobacterial activity.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Discovery of a near-infrared fluorescent probe for G-quadruplexes by exploiting the concept of unfolding-intramolecular-aggregation-induced emission

Xiao-Dong Wang, Yong-Si Liu, Ming-Hao Hu

Summary: In this study, a selffolded fluorescent probe was designed to selectively illuminate G4s by unfolding its intramolecular aggregation mediated by G4 binding. This probe showed more controllable background emission and promising ability to track G4 forming dynamics compared to previous disaggregation-induced emission (DIE) probes.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Potential therapeutic medicines for renal fibrosis: Small-molecule compounds and natural products

Yu Xiang, Zhuo Yuan, Qichuan Deng, Linshen Xie, Dongke Yu, Jianyou Shi

Summary: This review provides a brief description of the diagnosis, pathogenesis, and potential therapeutic inhibitors for renal fibrosis. Currently, there are no clear therapeutic targets or drugs for renal fibrosis; however, some natural products may have potential efficacy for treating renal fibrosis.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Boron-containing carbonic anhydrases inhibitors

Simone Giovannuzzi, Anna Nikitjuka, Bruna Rafaela Pereira Resende, Michael Smietana, Alessio Nocentini, Claudiu T. Supuran, Jean-Yves Winum

Summary: Boron-based compounds have been extensively studied in medicinal chemistry, playing a crucial role in designing small molecule drugs for various diseases. Boron is particularly valuable in developing inhibitors for metalloenzymes carbonic anhydrases, and it can modulate ligand recognition ability and selectivity. Recent advancements have led to the discovery of novel boron-based inhibitors that can inhibit carbonic anhydrases through a Lewis acid-base mechanism. Further research is needed to fully explore the potential of boron-based inhibitors and advance their clinical applications.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Acid-triggered controlled release and fluorescence-switchable phthalocyanine nanoassemblies combined with O2-economizer for tumor imaging and collaborative photodynamic antitumor therapy

Xinxin Liu, Lei Chen, Ze Chen

Summary: This study developed a nanostructured photosensitizer loaded with oxygen-throttling drug and demonstrated its enhanced cytotoxicity against tumor cells under hypoxic conditions. Animal experiments showed the enhanced tumor targeting capability of the photosensitizer and its inhibitory effect on tumor growth.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Casuattimines A-N, fourteen new Lycopodium alkaloids from Lycopodiastrum casuarinoides with Cav3.1 channel inhibitory activity

Shuai Jiang, Wen-Yan Li, Zai-Feng Yuan, Qin-Shi Zhao

Summary: This study isolated two new dimeric Lycopodium alkaloids and twelve previously undescribed Lycopodium alkaloids from Lycopodiastrum casuarinoides. The structures of these compounds were determined and their inhibitory activities on the Cav3.1 channel were evaluated.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Nucleolus imaging based on naphthalimide derivatives

Yan Yang, Dong-Xiao Yan, Rui-Xue Rong, Bing-Ye Shi, Man Zhang, Jing Liu, Jie Xin, Tao Xu, Wen-Jie Ma, Xiao-Liu Li, Ke-Rang Wang

Summary: In this study, a series of nucleolar fluorescent probes based on naphthalimide derivatives were designed and synthesized, which could achieve clear nucleolar staining in living cells. The results showed that these probes exhibited good targeting to the cell nucleolus and could bind to RNA and enhance fluorescence. This has positive implications for the diagnosis and treatment of nucleolus-related diseases.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Synthesis and bioevaluation of Scutellarein-Tertramethylpyrazine hybrid molecules for the treatment of ischemic stroke

Yongxi Dong, Fang Wang, Jinlan Wen, Yongqing Mao, Shanhui Zhang, Tiemei Long, Zhangxiang Yang, Lei Li, Jiquan Zhang, Li Dong, Gang Liu, Jianwei Xu

Summary: The hybrid molecules of Scutellarein and Tertramethylpyrazine show excellent neuroprotective and antiplatelet effects in the treatment of ischemic stroke. Compound 1e is particularly effective, enhancing cell membrane permeability and inhibiting cell uptake, as well as significantly reducing cerebral infarction volume.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

From bacteria to biomedicine: Developing therapies exploiting NAD plus metabolism

Yu Chen, Yuanyuan Ying, Jonathan Lalsiamthara, Yuheng Zhao, Saber Imani, Xin Li, Sijing Liu, Qingjing Wang

Summary: This paper examines the role and metabolic regulation of NAD+ in bacteria, highlighting its impact on physiology and virulence. It explores enzymes associated with NAD+ metabolism as potential targets for antibacterial drugs and vaccine candidates. Additionally, it scrutinizes the medical potential of NAD+ and provides insights for its application in biomedicine.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

A new fluorescent probe for the visualization of progerin

Jon Macicior, Daniel Fernandez, Silvia Ortega-Gutierrez

Summary: Hutchinson-Gilford progeria syndrome (HGPS), also known as progeria, is a rare genetic disease that causes premature aging and significantly reduces life expectancy. Currently, there is only one approved drug for treating progeria, but its efficacy is limited. Progerin levels are believed to be the most important biomarker related to disease severity.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Assessing the effectiveness of fluorinated and α-methylated 3-boronophe-nylalanine for improved tumor-specific boron delivery in boron neutron capture therapy

Fuko Hirano, Naoya Kondo, Yusuke Murata, Aya Sudani, Takashi Temma

Summary: Fluorinated alpha-methyl 3BPA derivatives showed improved water solubility, tumor targetability, and biodistribution compared to 3BPA and BPA, resulting in significantly improved tumor-to-normal tissue ratios.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Discovery of novel 5-phenylpyrazol receptor interacting protein 1(RIP1) kinase inhibitors as anti-necroptosis agents by combining virtual screening and in vitro and in vivo experimental evaluations

Ying Shi, Jiaqin Tang, Shumeng Zhi, Ruiqi Jiang, Qing Huang, Lei Sun, Zhizhong Wang, Yanran Wu

Summary: Necroptosis is a type of cell death associated with various diseases. In this study, we identified a small molecule inhibitor, SY-1, that effectively blocks necroptosis by inhibiting the phosphorylation of RIP1/RIP3/MLKL pathway. SY-1 also showed protective effects against TNF-induced hypothermia and improved survival in mice with SIRS. These findings highlight the potential therapeutic applications of SY-1.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Exploring the reactivity of bicyclic α-iminophosphonates to access new imidazoline I2 receptor ligands

Andrea Bagan, Sonia Abas, Judith Pala-Pujadas, Alba Irisarri, Christian Grinan-Ferre, Merce Pallas, Itziar Muneta-Arrate, Carolina Muguruza, Luis F. Callado, Belen Perez, Elies Molins, Jose A. Morales-Garcia, Carmen Escolano

Summary: Recent studies have identified the modulation of imidazoline I-2 receptors (I-2-IR) by selective ligands as a potential strategy for treating neurodegenerative diseases. This study reports a family of bicyclic alpha-iminophosphonates that show high affinity and selectivity for I-2-IR and demonstrates their neuroprotective and anti-inflammatory effects in in vitro and in vivo models. The findings emphasize the importance of exploring structurally novel I-2-IR ligands for therapeutic strategies in neurodegeneration.

BIOORGANIC CHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Discovery of a potent and selective CBP bromodomain inhibitor (Y08262) for treating acute myeloid leukemia

Qiuping Xiang, Tianbang Wu, Cheng Zhang, Chao Wang, Hongrui Xu, Qingqing Hu, Jiankang Hu, Guolong Luo, Xiaoxi Zhuang, Xishan Wu, Yan Zhang, Yong Xu

Summary: This study reports the discovery of a 1-(indolizin-3-yl)ethan-1-one derivative as a potent and selective CBP bromodomain inhibitor for AML drug development.

BIOORGANIC CHEMISTRY (2024)