Organoboronic acids/esters as effective drug and prodrug candidates in cancer treatments: challenge and hope

Abstract Boronic acids/esters have recently emerged in the field of medicinal and pharmaceutical research due to their exceptional oxophilicity, low toxicity, and unique structure. They are known as potent enzyme inhibitors, cancer therapy capture agents, and can mimic certain types of antibodies to fight infections. They have been designed and developed into drugs, and this approach has emerged in the last 20 years. Five boronic acid drugs have been approved by the FDA and Health Canada, two of which are used to treat cancer, specifically multiple myeloma. The purpose of this review is to investigate boronic acid/ester derivatives as potential pharmaceutical agents as well as the mechanism of action. It will concentrate on six types of cancer: multiple myeloma, prostate cancer, breast cancer, lung cancer, cervical cancer, and colon cancer. Some newly developed boron-containing compounds have already demonstrated highly promising activities, but further investigation is required before final conclusions can be drawn.

[1]  F. Kar,et al.  Borax regulates iron chaperone‐ and autophagy‐mediated ferroptosis pathway in glioblastoma cells , 2023, Environmental toxicology.

[2]  Wen Zhang,et al.  Design and discovery of novel dipeptide boronic acid ester proteasome inhibitors, an oral slowly-released prodrug for the treatment of multiple myeloma. , 2023, European journal of medicinal chemistry.

[3]  F. Kar,et al.  The dual role of boron in vitro neurotoxication of glioblastoma cells via SEMA3F/NRP2 and ferroptosis signaling pathways , 2022, Environmental toxicology.

[4]  Andrzej S. Skwarecki,et al.  Inhibitors of glucosamine-6-phosphate synthase as potential antimicrobials or antidiabetics – synthesis and properties , 2022, Journal of enzyme inhibition and medicinal chemistry.

[5]  V. Mirsky,et al.  3-Thienylboronic Acid as a Receptor for Diol-Containing Compounds: A Study by Isothermal Titration Calorimetry , 2022, Chemosensors.

[6]  T. Yang,et al.  Natural source, bioactivity and synthesis of 3-Arylcoumarin derivatives , 2022, Journal of enzyme inhibition and medicinal chemistry.

[7]  G. Tranmer,et al.  The Boron Advantage: The Evolution and Diversification of Boron’s Applications in Medicinal Chemistry , 2022, Pharmaceuticals.

[8]  P. Ambarcioglu,et al.  Calcium fructoborate regulate colon cancer (Caco‐2) cytotoxicity through modulation of apoptosis , 2022, Journal of biochemical and molecular toxicology.

[9]  M. Özgöçmen,et al.  Boric acid suppresses cell proliferation by TNF signaling pathway mediated apoptosis in SW-480 human colon cancer line. , 2022, Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements.

[10]  Takumi Watanabe,et al.  [Boronic Acid as a Promising Class of Chemical Entity for Development of Clinical Medicine for Targeted Therapy of Cancer]. , 2022, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.

[11]  F. Şahin,et al.  Anti-cancer effect of boron derivatives on small-cell lung cancer. , 2022, Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements.

[12]  A. Yarat,et al.  Brain Boron Level, DNA Content, and Myeloperoxidase Activity of Metformin-Treated Rats in Diabetes and Prostate Cancer Model , 2021, Biological Trace Element Research.

[13]  X. Lei,et al.  Discovery and development of tumor glycolysis rate-limiting enzyme inhibitors. , 2021, Bioorganic chemistry.

[14]  A. Bani-Yaseen Computational Study on the Mechanism of the Photouncaging Reaction of Vemurafenib: Toward an Enhanced Photoprotection Approach for Photosensitive Drugs , 2021, Molecules.

[15]  M. Offidani,et al.  Novel Experimental Drugs for Treatment of Multiple Myeloma , 2021, Journal of experimental pharmacology.

[16]  D. Trifiletti,et al.  Boron Neutron Capture Therapy: A Review of Clinical Applications , 2021, Frontiers in Oncology.

[17]  A. Jemal,et al.  Global Cancer Statistics 2020: GLOBOCAN Estimates of Incidence and Mortality Worldwide for 36 Cancers in 185 Countries , 2021, CA: a cancer journal for clinicians.

[18]  E. Dogan Computational Bioactivity Analysis and Bioisosteric Investigation of the Approved Breast Cancer Drugs Proposed New Design Drug Compounds: Increased Bioactivity Coming with Silicon and Boron , 2021, Letters in Drug Design & Discovery.

[19]  Jhinuk Chatterjee,et al.  The Use of In Silico Tools for the Toxicity Prediction of Potential Inhibitors of SARS-CoV-2 , 2021, Alternatives to laboratory animals : ATLA.

[20]  M. Bilgin,et al.  Evaluation of the Anti-cancer and Biological Effects of Boric Acid on Colon Cancer Cell Line , 2020, Meandros Medical and Dental Journal.

[21]  A. Bani-Yaseen The supramolecular host-guest complexation of Vemurafenib with β-cyclodextrin and cucurbit[7]uril as drug photoprotecting systems: A DFT/TD-DFT study , 2020 .

[22]  Y. Kara,et al.  Effects of Curcumin and Boric Acid Against Neurodegenerative Damage Induced by Amyloid Beta (1-42) , 2020, Biological Trace Element Research.

[23]  A. Bani-Yaseen Investigation on the impact of solvent on the photochemical properties of the photoactive anticancer drug Vemurafenib: A computational study , 2020 .

[24]  P. Aggett,et al.  Use of mechanistic information to derive chemical-specific adjustment factors - Refinement of risk assessment. , 2020, Regulatory toxicology and pharmacology : RTP.

[25]  C. Skarbek,et al.  Anticancer boron-containing prodrugs responsive to oxidative stress from the tumor microenvironment. , 2020, European journal of medicinal chemistry.

[26]  Minoru Suzuki,et al.  Preclinical study of boron neutron capture therapy for bone metastasis using human breast cancer cell lines. , 2020, Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine.

[27]  S. Perna,et al.  Pivotal role of boron supplementation on bone health: A narrative review. , 2020, Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements.

[28]  H. Senturk,et al.  In Vivo Assessment of the Effect of Hexagonal Boron Nitride Nanoparticles on Biochemical, Histopathological, Oxidant and Antioxidant Status , 2020, Journal of Cluster Science.

[29]  P. Waldron,et al.  Proteasome inhibitor‐associated thrombotic microangiopathy: A review of cases reported to the FDA adverse event reporting system and published in the literature , 2020, American journal of hematology.

[30]  T. Liang,et al.  Discovery of Peptide Boronate Derivatives as Histone Deacetylase (HDAC) and Proteasome Dual Inhibitors for Overcoming Bortezomib Resistance of Multiple Myeloma. , 2020, Journal of medicinal chemistry.

[31]  N. Moitessier,et al.  Design and discovery of boronic acid drugs. , 2020, European journal of medicinal chemistry.

[32]  R. McDonald,et al.  Regioselective synthesis of ortho-iodobiphenylboronic acid derivatives: a superior catalyst for carboxylic acid activation , 2020 .

[33]  B. Keppler,et al.  Reactive Oxygen Species (ROS)-Sensitive Prodrugs of the Tyrosine Kinase Inhibitor Crizotinib , 2020, Molecules.

[34]  Zhuxian Zhou,et al.  Self-assembly of oxidation-responsive polyethylene glycol-paclitaxel prodrug for cancer chemotherapy. , 2020, Journal of controlled release : official journal of the Controlled Release Society.

[35]  A. Coca,et al.  The Chemistry of Organoboron Species: Classification and Basic Properties , 2019 .

[36]  Shanchun Guo,et al.  Metabolism and Pharmacokinetic Study of the Boron-Containing Prodrug of Belinostat (ZL277), a Pan HDAC Inhibitor with Enhanced Bioavailability , 2019, Pharmaceuticals.

[37]  Kui Luo,et al.  A dithiocarbamate-based H2O2-responsive prodrug for combinational chemotherapy and oxidative stress amplification therapy. , 2019, Chemical communications.

[38]  W. Denny,et al.  Boron in drug design: Recent advances in the development of new therapeutic agents. , 2019, European journal of medicinal chemistry.

[39]  M. Clausen,et al.  Prodrug strategies for targeted therapy triggered by reactive oxygen species. , 2019, MedChemComm.

[40]  H. Senturk,et al.  The Role of Oxidative Stress, Renal Inflammation, and Apoptosis in Post Ischemic Reperfusion Injury of Kidney Tissue: the Protective Effect of Dose-Dependent Boric Acid Administration , 2019, Biological Trace Element Research.

[41]  Huchen Zhou,et al.  Design, Synthesis, and Structure-Activity Relationship of 7-Propanamide Benzoxaboroles as Potent Anticancer Agents. , 2019, Journal of medicinal chemistry.

[42]  Pedro M. P. Gois,et al.  Boronic acids as building blocks for the construction of therapeutically useful bioconjugates. , 2019, Chemical Society reviews.

[43]  Y. Zhang,et al.  MicroRNAs, intestinal inflammatory and tumor. , 2019, Bioorganic & medicinal chemistry letters.

[44]  V. Sahinturk,et al.  High Concentrations of Boric Acid Trigger Concentration-Dependent Oxidative Stress, Apoptotic Pathways and Morphological Alterations in DU-145 Human Prostate Cancer Cell Line , 2019, Biological Trace Element Research.

[45]  K. Kuroda,et al.  The proteasome inhibitor, bortezomib, induces prostate cancer cell death by suppressing the expression of prostate-specific membrane antigen, as well as androgen receptor. , 2019, International journal of oncology.

[46]  F. Shieh,et al.  Chikungunya virus inhibition by synthetic coumarin-guanosine conjugates. , 2019, European journal of medicinal chemistry.

[47]  Meng Lei,et al.  Discovery of a novel dipeptidyl boronic acid proteasome inhibitor for the treatment of multiple myeloma and triple-negative breast cancer. , 2019, Organic & biomolecular chemistry.

[48]  Huyuan Yang,et al.  All-oral ixazomib, cyclophosphamide, and dexamethasone for transplant-ineligible patients with newly diagnosed multiple myeloma. , 2019, European journal of cancer.

[49]  D M Parkin,et al.  Estimating the global cancer incidence and mortality in 2018: GLOBOCAN sources and methods , 2018, International journal of cancer.

[50]  Yan Shu,et al.  Enhanced Tumor Selectivity of 5-Fluorouracil Using a Reactive Oxygen Species-Activated Prodrug Approach. , 2018, ACS medicinal chemistry letters.

[51]  P. Lacal,et al.  Therapeutic implication of vascular endothelial growth factor receptor‐1 (VEGFR‐1) targeting in cancer cells and tumor microenvironment by competitive and non‐competitive inhibitors , 2018, Pharmacological research.

[52]  A. Jemal,et al.  Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries , 2018, CA: a cancer journal for clinicians.

[53]  M. Beksac,et al.  The safety of bortezomib for the treatment of multiple myeloma , 2018, Expert opinion on drug safety.

[54]  R. Govindan,et al.  Tumor Mutation Burden as a Biomarker in Resected Non-Small-Cell Lung Cancer. , 2018, Journal of clinical oncology : official journal of the American Society of Clinical Oncology.

[55]  Robert D. Eagling,et al.  Handbook of Boron Science , 2018, Handbook of Boron Science.

[56]  Haseeb Khaliq,et al.  The Physiological Role of Boron on Health , 2018, Biological Trace Element Research.

[57]  F. Feng,et al.  Small molecule KDM4s inhibitors as anti-cancer agents , 2018, Journal of enzyme inhibition and medicinal chemistry.

[58]  Jian Zhang,et al.  Zinc binding groups for histone deacetylase inhibitors , 2018, Journal of enzyme inhibition and medicinal chemistry.

[59]  M. Vallet‐Regí,et al.  Self-immolative chemistry in nanomedicine , 2017, 2104.10944.

[60]  R. McDonald,et al.  Design, Synthesis and X‐ray Crystal Structure of Iodinated Benzoboroxole Derivatives by Consecutive Metal–Iodine Exchange of 3,4,5‐Triiodoanisole , 2017 .

[61]  R. McDonald,et al.  Mild, Efficient, and Regioselective Synthesis of Diiodophenylboronic Acid Derivatives via Metal–Iodine Exchange of 5-Substituted 1,2,3-Triiodoarenes , 2017, Synthesis.

[62]  J. Leroux,et al.  Ratiometric Fluorescent Probes for the Detection of Reactive Oxygen Species. , 2017, Chemistry.

[63]  Jianbin Tang,et al.  A Tumor‐Specific Cascade Amplification Drug Release Nanoparticle for Overcoming Multidrug Resistance in Cancers , 2017, Advanced materials.

[64]  Huyuan Yang,et al.  Dose and Schedule Selection of the Oral Proteasome Inhibitor Ixazomib in Relapsed/Refractory Multiple Myeloma: Clinical and Model-Based Analyses , 2017, Targeted Oncology.

[65]  Q. Dou,et al.  The preclinical discovery and development of bortezomib for the treatment of mantle cell lymphoma , 2017, Expert opinion on drug discovery.

[66]  S. Vincent Rajkumar,et al.  Ixazomib cardiotoxicity: A possible class effect of proteasome inhibitors , 2017, American journal of hematology.

[67]  R. Vij,et al.  Phase I/II study of the novel proteasome inhibitor delanzomib (CEP-18770) for relapsed and refractory multiple myeloma , 2017, Leukemia & lymphoma.

[68]  Y. Bando,et al.  Hollow boron nitride nanospheres as boron reservoir for prostate cancer treatment , 2017, Nature Communications.

[69]  Xin Wang,et al.  Urea-containing peptide boronic acids as potent proteasome inhibitors. , 2017, European journal of medicinal chemistry.

[70]  N. Aswath,et al.  Boron Neutron Capture Therapy - A Literature Review. , 2016, Journal of clinical and diagnostic research : JCDR.

[71]  A. Deiters,et al.  Alcohol, Aldehyde, and Ketone Liberation and Intracellular Cargo Release through Peroxide-Mediated α-Boryl Ether Fragmentation. , 2016, Journal of the American Chemical Society.

[72]  E. Shimosegawa,et al.  Assessment of 10B concentration in boron neutron capture therapy: potential of image-guided therapy using 18FBPA PET , 2016, Annals of Nuclear Medicine.

[73]  Jiawang Liu,et al.  Fulvestrant-3 Boronic Acid (ZB716): An Orally Bioavailable Selective Estrogen Receptor Downregulator (SERD). , 2016, Journal of medicinal chemistry.

[74]  Huyuan Yang,et al.  Pharmacokinetics of ixazomib, an oral proteasome inhibitor, in solid tumour patients with moderate or severe hepatic impairment , 2016, British journal of clinical pharmacology.

[75]  Huyuan Yang,et al.  A pharmacokinetics and safety phase 1/1b study of oral ixazomib in patients with multiple myeloma and severe renal impairment or end‐stage renal disease requiring haemodialysis , 2016, British journal of haematology.

[76]  M. Shirley Ixazomib: First Global Approval , 2016, Drugs.

[77]  L. Meijer,et al.  Discovery of the First Potent and Selective Inhibitors of Human dCTP Pyrophosphatase 1. , 2016, Journal of medicinal chemistry.

[78]  A. Azab,et al.  Spotlight on ixazomib: potential in the treatment of multiple myeloma , 2016, Drug design, development and therapy.

[79]  D. Ariely,et al.  Disturbing Trends in Physician Burnout and Satisfaction With Work-Life Balance: Dealing With Malady Among the Nation's Healers. , 2015, Mayo Clinic proceedings.

[80]  Adam D Brooks,et al.  Design, Synthesis, and Characterization of Small-Molecule Reagents That Cooperatively Provide Dual Readouts for Triaging and, When Necessary, Quantifying Point-of-Need Enzyme Assays. , 2015, The Journal of organic chemistry.

[81]  L. Pizzorno Nothing Boring About Boron. , 2015, Integrative medicine.

[82]  Ahmed Alouane,et al.  Self-immolative spacers: kinetic aspects, structure-property relationships, and applications. , 2015, Angewandte Chemie.

[83]  L. Miele,et al.  Boronic prodrug of endoxifen as an effective hormone therapy for breast cancer , 2015, Breast Cancer Research and Treatment.

[84]  A. Abazid,et al.  Terminal versus Internal Diiodobenzyl Alcohol Derivatives via Regioselective Metal–Iodine Exchange of 1,2,3-Triiodoarenes: Synthesis and Antibacterial Activity , 2015 .

[85]  I. Kato,et al.  Boronophenylalanine, a boron delivery agent for boron neutron capture therapy, is transported by ATB0,+, LAT1 and LAT2 , 2015, Cancer science.

[86]  Kristin E. Yamada,et al.  Boric acid induces cytoplasmic stress granule formation, eIF2α phosphorylation, and ATF4 in prostate DU-145 cells , 2014, BioMetals.

[87]  W. Knauf,et al.  Treatment of Non-Transplant Patients with Multiple Myeloma: Routine Treatment by Office-Based Haematologists in Germany - Data from the Prospective Tumour Registry Lymphatic Neoplasms (TLN) , 2014, Oncology Research and Treatment.

[88]  F. Nielsen Update on human health effects of boron. , 2014, Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements.

[89]  K. Hong,et al.  An activatable prodrug for the treatment of metastatic tumors. , 2014, Journal of the American Chemical Society.

[90]  Daniel J. Sargent,et al.  Drug rechallenge and treatment beyond progression—implications for drug resistance , 2013, Nature Reviews Clinical Oncology.

[91]  Xiaohua Peng,et al.  Substituent effects on oxidation-induced formation of quinone methides from arylboronic ester precursors. , 2013, Chemistry.

[92]  Yan Wang,et al.  In silico investigations of potential anabolic treatments in multiple myeloma-induced bone disease. , 2013, Bone.

[93]  A. Verma,et al.  Boron chemicals in diagnosis and therapeutics. , 2013, Future medicinal chemistry.

[94]  L. Ciani,et al.  Boron as a platform for new drug design , 2012, Expert opinion on drug discovery.

[95]  E. Fernández,et al.  Disclosing the structure/activity correlation in trivalent boron-containing compounds: a tendency map. , 2012, Chemistry.

[96]  P. Floreancig,et al.  Versatile approach to α-alkoxy carbamate synthesis and stimulus-responsive alcohol release. , 2012, Organic & biomolecular chemistry.

[97]  J. Joseph,et al.  Boronate probes as diagnostic tools for real time monitoring of peroxynitrite and hydroperoxides. , 2012, Chemical research in toxicology.

[98]  V. Gandhi,et al.  ROS-activated anticancer prodrugs: a new strategy for tumor-specific damage. , 2012, Therapeutic delivery.

[99]  N. Hosmane,et al.  New classes of carborane-appended 5-thio-D-glucopyranose derivatives. , 2012, Dalton transactions.

[100]  C. Hunt Dietary boron: progress in establishing essential roles in human physiology. , 2012, Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements.

[101]  H. Goldschmidt,et al.  European perspective on multiple myeloma treatment strategies: update following recent congresses. , 2012, The oncologist.

[102]  J. Bradner,et al.  Preclinical activity, pharmacodynamic, and pharmacokinetic properties of a selective HDAC6 inhibitor, ACY-1215, in combination with bortezomib in multiple myeloma. , 2012, Blood.

[103]  N. Hosmane,et al.  Future Perspectives for Boron and Gadolinium Neutron Capture Therapies in Cancer Treatment , 2012 .

[104]  V. Gandhi,et al.  Hydrogen peroxide inducible DNA cross-linking agents: targeted anticancer prodrugs. , 2011, Journal of the American Chemical Society.

[105]  D. Hall Structure, Properties, and Preparation of Boronic Acid Derivatives , 2011 .

[106]  G. Plopper,et al.  Phenylboronic acid is a more potent inhibitor than boric acid of key signaling networks involved in cancer cell migration , 2011, Cell adhesion & migration.

[107]  Wei Wang,et al.  Effect of Boron on Osteogenic Differentiation of Human Bone Marrow Stromal Cells , 2011, Biological Trace Element Research.

[108]  J. Joseph,et al.  Reaction between peroxynitrite and boronates: EPR spin-trapping, HPLC Analyses, and quantum mechanical study of the free radical pathway. , 2011, Chemical research in toxicology.

[109]  S. Rees,et al.  Principles of early drug discovery , 2011, British journal of pharmacology.

[110]  T. Muchamuel,et al.  Nonproteasomal Targets of the Proteasome Inhibitors Bortezomib and Carfilzomib: a Link to Clinical Adverse Events , 2011, Clinical Cancer Research.

[111]  Di Chen,et al.  Bortezomib as the first proteasome inhibitor anticancer drug: current status and future perspectives. , 2011, Current cancer drug targets.

[112]  Petre Rotaru,et al.  Calcium Fructoborate—Potential Anti-inflammatory Agent , 2011, Biological Trace Element Research.

[113]  Y. Kuo,et al.  Risk of colorectal cancer in men on long-term androgen deprivation therapy for prostate cancer. , 2010, Journal of the National Cancer Institute.

[114]  R. Popa,et al.  Boron-containing compounds as preventive and chemotherapeutic agents for cancer. , 2010, Anti-cancer agents in medicinal chemistry.

[115]  L. Dick,et al.  Building on bortezomib: second-generation proteasome inhibitors as anti-cancer therapy. , 2010, Drug discovery today.

[116]  M. Rolfe,et al.  Evaluation of the proteasome inhibitor MLN9708 in preclinical models of human cancer. , 2010, Cancer research.

[117]  H. Ban,et al.  Boron-containing phenoxyacetanilide derivatives as hypoxia-inducible factor (HIF)-1alpha inhibitors. , 2010, Bioorganic & medicinal chemistry letters.

[118]  J. Russo,et al.  Estrogen and Xenoestrogens in Breast Cancer , 2010, Toxicologic pathology.

[119]  J. Joseph,et al.  Direct oxidation of boronates by peroxynitrite: mechanism and implications in fluorescence imaging of peroxynitrite. , 2009, Free radical biology & medicine.

[120]  Yi Xia,et al.  Therapeutic potential of boron-containing compounds. , 2009, Future medicinal chemistry.

[121]  K. R. Maples,et al.  Discovery and structure-activity study of a novel benzoxaborole anti-inflammatory agent (AN2728) for the potential topical treatment of psoriasis and atopic dermatitis. , 2009, Bioorganic & medicinal chemistry letters.

[122]  A. LeBeau,et al.  Potent and selective peptidyl boronic acid inhibitors of the serine protease prostate-specific antigen. , 2008, Chemistry & biology.

[123]  A. Matsumura,et al.  Boron neutron capture therapy for glioblastoma. , 2008, Cancer letters.

[124]  K. Gademann,et al.  Secondary Metabolites from Cyanobacteria: Complex Structures and Powerful Bioactivities , 2008 .

[125]  V. Mitran,et al.  Comparative Effects of Boric Acid and Calcium Fructoborate on Breast Cancer Cells , 2008, Biological Trace Element Research.

[126]  M. Spitz,et al.  Dietary boron and hormone replacement therapy as risk factors for lung cancer in women. , 2007, American journal of epidemiology.

[127]  U. Peters,et al.  Boron intake and prostate cancer risk , 2007, Cancer Causes & Control.

[128]  C. C. Cunningham Talabostat , 2007, Expert opinion on investigational drugs.

[129]  Irma H. Russo,et al.  The role of estrogen in the initiation of breast cancer , 2006, The Journal of Steroid Biochemistry and Molecular Biology.

[130]  S. Baker,et al.  Discovery of a new boron-containing antifungal agent, 5-fluoro-1,3-dihydro-1-hydroxy-2,1- benzoxaborole (AN2690), for the potential treatment of onychomycosis. , 2006, Journal of medicinal chemistry.

[131]  L. Shapiro,et al.  Identification of borinic esters as inhibitors of bacterial cell growth and bacterial methyltransferases, CcrM and MenH. , 2005, Journal of medicinal chemistry.

[132]  M. Vicente,et al.  Boron Neutron Capture Therapy of Cancer: Current Status and Future Prospects , 2005, Clinical Cancer Research.

[133]  C. Eckhert,et al.  Boric acid inhibits human prostate cancer cell proliferation. , 2004, Cancer letters.

[134]  D. Karunagaran,et al.  Ectopic expression of Bcl-XL or Ku70 protects human colon cancer cells (SW480) against curcumin-induced apoptosis while their down-regulation potentiates it. , 2004, Carcinogenesis.

[135]  R. Pazdur,et al.  Approval Summary for Bortezomib for Injection in the Treatment of Multiple Myeloma , 2004, Clinical Cancer Research.

[136]  T. Habuchi,et al.  Functional Correlation of Trophinin Expression with the Malignancy of Testicular Germ Cell Tumor , 2004, Cancer Research.

[137]  J. Adams The development of proteasome inhibitors as anticancer drugs. , 2004, Cancer cell.

[138]  D. Steinberg,et al.  Synthesis and evaluation of oxazaborolidines for antibacterial activity against Streptococcus mutans. , 2004, Journal of medicinal chemistry.

[139]  Zuo-Feng Zhang,et al.  Dietary boron intake and prostate cancer risk. , 2004, Oncology reports.

[140]  R. Maronpot,et al.  Boron Supplementation Inhibits the Growth and Local Expression of IGF-1 in Human Prostate Adenocarcinoma (LNCaP) Tumors in Nude Mice , 2004, Toxicologic pathology.

[141]  G. Giles,et al.  Men with colorectal cancer are predisposed to prostate cancer , 2003, ANZ journal of surgery.

[142]  S. Batra,et al.  Current status of the molecular genetics of human prostatic adenocarcinomas , 2003, International journal of cancer.

[143]  B. Bassler,et al.  Structural identification of a bacterial quorum-sensing signal containing boron , 2002, Nature.

[144]  V. Akila,et al.  Information , 2001, The Lancet.

[145]  D W Rice,et al.  Mechanism of action of diazaborines. , 1998, Biochemical pharmacology.

[146]  P. Ramachandran,et al.  Organoboranes for synthesis 17. Generality of hydroboration-amination for the conversion of terpenes into enantiomerically pure terpenylamines. Their utility for gas chromatographic analysis of chiral carboxylic acids , 1996 .

[147]  B. Huber,et al.  Inhibition of dipeptidyl aminopeptidase IV (DP-IV) by Xaa-boroPro dipeptides and use of these inhibitors to examine the role of DP-IV in T-cell function. , 1991, Proceedings of the National Academy of Sciences of the United States of America.

[148]  B. Austin Novel pharmaceutical compounds from marine bacteria. , 1989, The Journal of applied bacteriology.

[149]  Y. Mori,et al.  Complex formation of p-boronophenylalanine with some monosaccharides. , 1989, Pigment cell research.

[150]  R. Brueggemeier,et al.  Synthesis and biochemical evaluation of inhibitors of estrogen biosynthesis. , 1978, Journal of medicinal chemistry.

[151]  H. Brodie,et al.  Studies on the mechanism of estrogen biosynthesis. 8. The development of inhibitors of the enzyme system in human placenta. , 1973, Endocrinology.

[152]  Xiaoyang Li,et al.  Advances and Challenges of HDAC Inhibitors in Cancer Therapeutics , 2018, Advances in cancer research.

[153]  H. Goldschmidt,et al.  Carfilzomib and dexamethasone versus bortezomib and dexamethasone for patients with relapsed or refractory multiple myeloma (ENDEAVOR): a randomised, phase 3, open-label, multicentre study. , 2016, The Lancet. Oncology.

[154]  T. Mitsudomi,et al.  Successes and limitations of targeted cancer therapy in lung cancer. , 2014, Progress in tumor research.

[155]  I. R. Scorei Calcium fructoborate: plant-based dietary boron as potential medicine for cancer therapy. , 2011, Frontiers in bioscience.

[156]  M. Hedayati,et al.  Comparative effects of daily and weekly boron supplementation on plasma steroid hormones and proinflammatory cytokines. , 2011, Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements.

[157]  M. Dreyling,et al.  Multiple myeloma: ESMO Clinical Practice Guidelines for diagnosis, treatment and follow-up. , 2010, Annals of oncology : official journal of the European Society for Medical Oncology.

[158]  Keiji Tanaka The proteasome: Overview of structure and functions , 2009, Proceedings of the Japan Academy. Series B, Physical and biological sciences.

[159]  J. Samet,et al.  Food and Drug Administration , 2007, BMJ : British Medical Journal.

[160]  C. H. Powell,et al.  Patty's Toxicology , 2001 .

[161]  J. Rees,et al.  What injection? , 1997, British Dental Journal.

[162]  H. Brodie,et al.  Studies on the mechanism of estrogen biosynthesis. 3. The stereochemistry of aromatization of C19 and C18 steroids. , 1968, Biochemistry.

[163]  O. Cope,et al.  Multiple myeloma. , 1948, The New England journal of medicine.