50,444 results match your criteria phosphonates

Incorporation of a FRET pair within a phosphonate diester.

Bioorg Chem 2021 May 30;114:105048. Epub 2021 May 30.

Department of Chemistry, The University of Iowa, Iowa City, IA 52245, United States; Department of Pharmacology, University of Iowa, Iowa City, IA 52242, United States. Electronic address:

Cell-cleavable protecting groups are an effective tactic for construction of biological probes because such compounds can improve problems with instability, solubility, and cellular uptake. Incorporation of fluorescent groups in the protecting groups may afford useful probes of cellular functions, especially for payloads containing phosphonates that would be highly charged if not protected, but little is known about the steric or electronic factors that impede release of the payload. In this report we present a strategy for the synthesis of a coumarin fluorophore and a 4-((4-(dimethylamino)phenyl)diazenyl)benzoic acid (DABCYL) ester chromophore incorporated as a FRET pair within a single phosphonate. Read More

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Introduction of a cyano group at the 2-position of an (,)-3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) derivative of thymine elicits selective anti-HBV activity.

RSC Med Chem 2021 May 29;12(5):804-808. Epub 2021 Apr 29.

KU Leuven, Rega Institute for Medical Research, Medicinal Chemistry Herestraat 49-Box 1041 3000 Leuven Belgium

The substantial impact of acyclic nucleoside phosphonates (ANPs) on human medicine encourages the synthesis of new ANP analogues with a potentially differentiated antiviral spectrum. Herein, we demonstrate the functionalization of the 2-position of the (,)-3-hydroxy-2-(phosphonomethoxy)propyl side-chain of an inactive ANP with a polar cyano group to generate a thymine analogue with selective inhibition of hepatitis B virus (HBV) replication (SI > 302; EC = 0.33 μM), without significant antiretroviral activity. Read More

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Chemotherapy with paclitaxel for recalcitrant molluscum contagiosum in an HIV-infected patient.

BMJ Case Rep 2021 Jun 10;14(6). Epub 2021 Jun 10.

Oncology, Highland Hospital w UCSF affiliation, Oakland, California, USA.

Molluscum contagiosum (MC) is a viral skin infection seen in children, sexually active adults and immunocompromised populations. It is usually a self-limiting illness that typically spontaneously resolves without therapeutic intervention. However, when the papules are extensive or refractory causing complications or aesthetic issues, multiple treatment modalities exist to relieve symptoms, limit spread and decrease the social stigma associated with visible lesions. Read More

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[Effect of tenofovir disoproxil fumarate antiviral therapy on virus-specific CD8+T Cells function in patients with chronic hepatitis B].

Zhonghua Gan Zang Bing Za Zhi 2021 May;29(5):421-426

Medical Section, The First Affiliated Hospital of Xinxiang Medical University, Xinxiang 453100, China.

To observe the effect of tenofovir disoproxil fumarate (TDF) antiviral therapy on HBV-specific CD8(+)T cell function in peripheral blood of patients with HBeAg-positive chronic hepatitis B, and to assess its correlation with HBeAg sero-negativeness. Sixty-three cases with HLA-A02 restricted HBeAg-positive chronic hepatitis B who received TDF (300 mg/d) antiviral therapy were enrolled from October 2016 to July 2018. The peripheral blood CD8(+)T cells were separated at baseline and 48 weeks after treatment. Read More

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Acyclic nucleoside phosphonates with 2-aminothiazole base as inhibitors of bacterial and mammalian adenylate cyclases.

Eur J Med Chem 2021 May 28;222:113581. Epub 2021 May 28.

Institute of Organic Chemistry and Biochemistry, The Czech Academy of Sciences, 16610, Prague 6, Czech Republic. Electronic address:

A series of novel acyclic nucleoside phosphonates (ANPs) was synthesized as potential adenylate cyclase inhibitors, where the adenine nucleobase of adefovir (PMEA) was replaced with a 5-substituted 2-aminothiazole moiety. The design was based on the structure of MB05032, a potent and selective inhibitor of fructose 1,6-bisphosphatase and a good mimic of adenosine monophosphate (AMP). From the series of eighteen novel ANPs, which were prepared as phosphoroamidate prodrugs, fourteen compounds were potent (single digit micromolar or submicromolar) inhibitors of Bordetella pertussis adenylate cyclase toxin (ACT), mostly without observed cytotoxicity in J774A. Read More

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Substrate Substitution in Kanosamine Biosynthesis Using Phosphonates and Phosphite Rescue.

Biochemistry 2021 Jun 7. Epub 2021 Jun 7.

Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK, Canada S7N 5C9.

Kanosamine is an antibiotic and antifungal compound synthesized from glucose 6-phosphate (G6P) in by the action of three enzymes: NtdC, which catalyzes NAD-dependent oxidation of the C3-hydroxyl; NtdA, a PLP-dependent aminotransferase; and NtdB, a phosphatase. We previously demonstrated that NtdC can also oxidize substrates such as glucose and xylose, though at much lower rates, suggesting that the phosphoryloxymethylene moiety of the substrate is critical for effective catalysis. To probe this, we synthesized two phosphonate analogues of G6P in which the bridging oxygen is replaced by methylene and difluoromethylene groups. Read More

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Extreme hypercalcaemia caused by immobilisation due to acute spinal cord injury.

BMJ Case Rep 2021 Jun 2;14(6). Epub 2021 Jun 2.

Internal Medicine, Amsterdam UMC Location VUmc, Amsterdam, The Netherlands

Hypercalcaemia due to immobilisation is an uncommon diagnosis and requires extensive evaluation to rule out common causes of hypercalcaemia such as primary hyperparathyroidism and malignancy.We report an unusual case of profound hypercalcaemia due to immobilisation in a young man due to acute spinal cord ischaemia, leading to paraplegia. Other causes of hypercalcaemia were ruled out and elevated bone turnover markers supported our hypothesis. Read More

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Toxicity assessment of organophosphorus in Ruditapes decussatus via physiological, chemical and biochemical determination: A case study with the compounds γ-oximo- and γ-amino-phosphonates and phosphine oxides.

Mar Pollut Bull 2021 May 31;169:112556. Epub 2021 May 31.

Laboratory of Environment Biomonitoring, Unit of coastal Ecology and Ecotoxicology, Faculty of Sciences of Bizerte, Jarzouna 7021, University of Carthage, Tunisia.

Organophosphorus derivatives are widely used in human health care and have been detected in aquatic ecosystems. These compounds may pose significant risks to non-target exposed organisms and only limited studies are available on bioconcentration and the effects of organophosphorus derivatives on marine organisms. The aim of this work was to evaluate the possible toxic effects of two concentrations (20 and 40 μg/L) of γ-oximo- and γ-amino-phosphonates and phosphine oxides in mediterranean clams Ruditapes decussatus exposed for 14 days using different biomarkers and the changes of filtration and respiration rate. Read More

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[Predictive relevance of KRAS mutational status in bone metastatic lung adenocarcinoma treated with bisphosphonate therapy].

Magy Onkol 2021 Jun 8;65(2):103-111. Epub 2021 May 8.

Mellkassebészeti Osztály, Országos Onkológiai Intézet, Budapest, Hungary.

The therapeutic impact of KRAS mutations remains controversial in bone metastatic lung adenocarcinoma (LADC). Therefore, our aim was to investigate the effects of KRAS mutational status on overall survival (OS) in these patients according to bisphosphonate therapy (BTx) and radiation therapy (RTx). In total, 134 LADC patients diagnosed with simultaneous bone metastasis were included in this study. Read More

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Synthesis of Functionalized Diethyl(pyrrolidin-2-yl)phosphonate and Diethyl(5-oxopyrrolidin-2-yl)phosphonate.

Molecules 2021 May 25;26(11). Epub 2021 May 25.

Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, 90-151 Lodz, Poland.

Short and efficient syntheses of functionalized (pyrrolidin-2-yl)phosphonate and (5-oxopyrrolidin-2-yl)phosphonate have been developed. The synthetic strategy involved the diastereospecific 1,3-dipolar cycloaddition of -benzyl--(diethoxyphosphoryl)nitrone to -1,4-dihydroxybut-2-ene and dimethyl maleate, respectively. ,-Diethyl 3-carbamoyl-4-hydroxy(5-oxopyrrolidin-2-yl)phosphonate was obtained from ,-diethyl 2-benzyl-4,5-dimethoxycarbonyl(isoxazolidin-3-yl)phosphonate by hydrogenation and subsequent treatment with ammonia, whereas transformation of ,-diethyl 2-benzyl-4,5-dihydroxymethyl(isoxazolidin-3-yl)phosphonate into ,-diethyl 3-aminomethyl-4-hydroxy(pyrrolidin-2-yl)phosphonate was accomplished by mesylation followed by hydrogenolysis to undergo intramolecular cyclization and the introduction of amino group via ammonolysis. Read More

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Radiotracers for Bone Marrow Infection Imaging.

Molecules 2021 May 25;26(11). Epub 2021 May 25.

Department of Nuclear Medicine, Aalborg University Hospital, DK-9000 Aalborg, Denmark.

Introduction: Radiotracers are widely used in medical imaging, using techniques of gamma-camera imaging (scintigraphy and SPECT) or positron emission tomography (PET). In bone marrow infection, there is no single routine test available that can detect infection with sufficiently high diagnostic accuracy. Here, we review radiotracers used for imaging of bone marrow infection, also known as osteomyelitis, with a focus on why these molecules are relevant for the task, based on their physiological uptake mechanisms. Read More

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Infection as an Important Factor in Medication-Related Osteonecrosis of the Jaw (MRONJ).

Medicina (Kaunas) 2021 May 9;57(5). Epub 2021 May 9.

Department of Oral and Maxillofacial Surgery and Facial Plastic Surgery, Ludwig-Maximilians-University, 80337 Munich, Germany.

Medication-related osteonecrosis of the jaw (MRONJ) has become a well-known side effect of antiresorptive, and antiangiogenic drugs commonly used in cancer management. Despite a considerable amount of literature addressing MRONJ, it is still widely accepted that the underlying pathomechanism of MRONJ is unclear. However, several clinical and preclinical studies indicate that infection seems to have a major role in the pathogenesis of MRONJ. Read More

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The Hydrolysis of Phosphinates and Phosphonates: A Review.

Molecules 2021 May 11;26(10). Epub 2021 May 11.

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary.

Phosphinic and phosphonic acids are useful intermediates and biologically active compounds which may be prepared from their esters, phosphinates and phosphonates, respectively, by hydrolysis or dealkylation. The hydrolysis may take place both under acidic and basic conditions, but the C-O bond may also be cleaved by trimethylsilyl halides. The hydrolysis of -esters is a challenging task because, in most cases, the optimized reaction conditions have not yet been explored. Read More

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Synthesis of Phosphonated Carbon Nanotubes: New Insight into Carbon Nanotubes Functionalization.

Materials (Basel) 2021 May 21;14(11). Epub 2021 May 21.

Institute of Biocybernetics, Biomedical Engineering of the Polish Academy of Sciences, 02-109 Warsaw, Poland.

Carbon nanotubes were successfully functionalized for the first time in a free radical phosphonylation reaction. Three synthetic protocols were proposed. Carbon nanotubes and diethylphosphite reacted in the presence of known radical initiator, such as azobisisobutyronitrile, single electron oxidant-Mn(OAc), or under UV radiation. Read More

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Development of selective bispecific Wnt mimetics for bone loss and repair.

Nat Commun 2021 05 31;12(1):3247. Epub 2021 May 31.

Surrozen, Inc., South San Francisco, CA, USA.

The Wnt signaling pathway is intricately connected with bone mass regulation in humans and rodent models. We designed an antibody-based platform that generates potent and selective Wnt mimetics. Using this platform, we engineer bi-specific Wnt mimetics that target Frizzled and low-density lipoprotein receptor-related proteins and evaluate their effects on bone accrual in murine models. Read More

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What would be the impact of COVID-19 on liver function of a patient with chronic hepatitis B? About a case and literature review.

Pan Afr Med J 2021 1;38:225. Epub 2021 Mar 1.

Faculty of Medicine and Pharmacy of Agadir, IBN ZOHR University, Hassan II Hospital, Agadir, Morocco.

Liver damage during COVID-19 disease has been described in numerous studies. Its mechanism is poorly understood. It is mainly reserved for severe forms and is manifested by abnormalities of the hepatic assessment and more particularly cytolysis. Read More

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Acute HSV and anti-NMDA encephalitis occurring as a neurosurgical complication.

BMJ Case Rep 2021 May 26;14(5). Epub 2021 May 26.

Universidad de los Andes, Bogota, Colombia.

We present a 24-year-old man with a 2-year history of progressive right-sided monocular vision loss with no other symptoms. An MRI showed a meningioma compressing the right optic nerve and the cavernous sinus. The tumour was partially resected. Read More

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One-step purification/extraction method to access glyphosate, glufosinate, and their metabolites in natural waters.

J Chromatogr A 2021 Jul 6;1649:462188. Epub 2021 May 6.

Laboratoire de Chimie Agro-Industrielle, LCA, Université de Toulouse, INRAE, 31030 Toulouse Cedex 4, France; Water - Environment - Oceanography Department, University of Science and Technology of Hanoi, Vietnam Academy of Science and Technology, 100000 Hanoi, Vietnam. Electronic address:

A new green method for trace level quantification of four herbicides, glyphosate (GLYP), glufosinate (GLUF), and their main metabolites, aminomethylphosphonic acid (AMPA) and 3-(methyl-phosphinico)-propionic acid (MPPA), was developed. The purification step without any derivatization was conducted by solid-phase extraction using Chelex-100 resin in the Fe (III) form, followed by elution with 5% NHOH. The four analytes were quantified by ultra-high-performance liquid chromatography coupled to tandem mass spectrometry. Read More

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Prevention and treatment of oral adverse effects of antiresorptive medications for osteoporosis - A position paper of the Brazilian Society of Endocrinology and Metabolism (SBEM), Brazilian Society of Stomatology and Oral Pathology (Sobep), and Brazilian Association for Bone Evaluation and Osteometabolism (Abrasso).

Arch Endocrinol Metab 2021 May;64(6):664-672

Departamento de Patologia e Diagnóstico Oral, Faculdade de Odontologia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, Brasil.

Antiresorptive therapy is the main form of prevention of osteoporotic or fragility fractures. Medication-related osteonecrosis of the jaw (MRONJ) is a relatively rare but severe adverse reaction to antiresorptive and antiangiogenic drugs. Physicians and dentists caring for patients taking these drugs and requiring invasive procedures face a difficult decision because of the potential risk of MRONJ. Read More

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Diverse synthetic approaches towards C1'-branched acyclic nucleoside phosphonates.

Org Biomol Chem 2021 May 25. Epub 2021 May 25.

Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 2, 160 00 Prague 6, Czech Republic.

Acyclic nucleoside phosphonates (ANPs) represent a significant class of antiviral, anticancer, and antiprotozoal compounds. It is therefore highly desirable to have diverse synthetic routes leading towards these molecules. In the past, many structural modifications were explored, but surprisingly, the field of C1'-branched ANPs has been neglected with only a handful of articles reporting their synthesis. Read More

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Tenofovir-induced osteomalacia with hypophosphataemia.

BMJ Case Rep 2021 May 24;14(5). Epub 2021 May 24.

General Internal Medicine, Department of Medicine, McGill University Health Centre, Montreal, Quebec, Canada

Tenofovir disoproxil fumarate (TDF) is an antiretroviral drug widely used as a first-line treatment of hepatitis B virus (HBV) and HIV. Increasing evidence has emerged associating its use with the development of Fanconi syndrome, renal insufficiency and bone disease. We report a case of a 61-year-old woman with a remote history of liver transplant for cirrhosis due to HBV. Read More

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Copper-Catalyzed Vicinal Cyano-, Thiocyano-, and Chlorophosphorylation of Alkynes: A Phosphinoyl Radical-Initiated Approach for Difunctionalized Alkenes.

Org Lett 2021 Jun 24;23(11):4342-4347. Epub 2021 May 24.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, Suzhou, Jiangsu 215123, China.

A copper-catalyzed difunctional cyano-, thiocyano-, and chlorophosphorylation reaction of alkynes with P(O)-H compounds and coupling partners (TBACN, TMSNCS, TMSCl) is described. The reaction introduces versatile groups (-P(O)R and -CN, -SCN, or -Cl) to form tri- and tetrasubstituted alkenyl phosphine oxides/phosphonates regio- and stereoselectively. Read More

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[A Rare Cause of Hypercalcemia].

Praxis (Bern 1994) 2021 ;110(7):397-402

Klinik für Innere Medizin, Zuger Kantonsspital.

A Rare Cause of Hypercalcemia Sarcoidosis is a rare cause of hypercalcemia, which is in most cases caused by primary hyperparathyroidism or a malignant tumor. Other rare causes include vitamin D intoxication, other granulomatous diseases (such as tuberculosis, or fungal infection) or mutiple myeloma. Because of the broad differential diagnosis, a systematic diagnostic approach is crucial to establish the correct diagnosis. Read More

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Why do some extraction sites develop medication-related osteonecrosis of the jaw and others do not? A within-patient study assessing radiographic predictors.

Int J Oral Implantol (Berl) 2021 Mar;14(1):87-98

Purpose: To compare radiographic predictors of medication-related osteonecrosis of the jaw in dental extraction sites.

Materials And Methods: Forty-one oncological patients undergoing intravenous or subcutaneous antiresorptive treatment, with a history of dental extraction visualised by panoramic imaging, were included in this retrospective study. Age-, sex- and extracted tooth-matched healthy patients who had previously undergone panoramic imaging were selected as controls (n = 57). Read More

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Synthesis and in vitro antitumour activity of 4(R)-methyl-3-O-phosphonomethyl-α-l-threose nucleosides.

Eur J Med Chem 2021 Oct 14;221:113513. Epub 2021 May 14.

Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education of China, School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, 450001, PR China. Electronic address:

A series of novel α-l-threose nucleoside phosphonate analogs, 4(R)-methyl-3-O-phosphonomethyl-α-l-threose nucleosides, were synthesized in multistep sequences starting from d-xylose. The synthetic sequence consisted of the following key stages: (i) the multistep synthesis of 1,2-O-isopropylidenyl-4(R)-methyl-3-O-phosphonomethyl-l-threose, (ii) the transformation of 1,2-O-isopropylidenyl sugar into suitable 1,2-di-O-acyl l-threose precursor, and (iii) the construction of target α-l-threose nucleoside phosphonate analogs by Vorbrüggen glycosidation reaction, deprotection of acyl group, and hydrolysis of diethyl group on phosphonate. The target nucleoside phosphonates were evaluated for their antitumour activities in cell culture-based assays. Read More

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October 2021

Synthesis of 1,3-Aminoalcohols and Spirocyclic Azetidines via Tandem Hydroxymethylation and Aminomethylation Reaction of β-Keto Phosphonates with -Nosyl--(2-bromoethyl)hydroxylamine.

Org Lett 2021 Jun 17;23(11):4152-4157. Epub 2021 May 17.

Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, P. R. China.

An unprecedented tandem α-hydroxymethylation and α-aminomethylation reaction of aromatic cyclic β-keto phosphonates with -nosyl--(2-bromoethyl)hydroxylamine in the presence of DBU base has been developed, affording a range of 1,3-aminoalcohols in good yields. The resultant products could be flexibly transformed into the spirocyclic and bispirocyclic azetidines via one step of Mitsunobu reaction. Mechanistic study revealed that hydroxylamine in situ generated the formaldehyde and nosylamide, which in turn triggered the sequential Horner-Wadsworth-Emmons, Michael, and aldol reactions. Read More

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Resorcin[4]arene-based multidentate phosphate ligands with superior binding affinity for nanocrystal surfaces.

Chem Commun (Camb) 2021 May;57(38):4694-4697

Department of Chemistry, University of Basel, Basel 4058, Switzerland.

We designed and synthesized two resorcin[4]arene scaffolds with four phosphate binding groups. The ligands effectively bind in at least a tridentate fashion at low surface coverage. The superior binding affinity is demonstrated using solution NMR spectroscopy and exceeds that of single phosphonates. Read More

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[Successful treatment with cidofovir for disseminated adenovirus infection accompanied by hemophagocytic syndrome and meningitis in an allogeneic hematopoietic stem cell transplantation recipient].

Rinsho Ketsueki 2021 ;62(4):251-256

Department of Hematology, Oita University Hospital.

A 65-year-old woman received bone marrow transplantation from an HLA-DRB1 one locus mismatched donor for high-risk myelodysplastic syndrome. On day 237 after transplantation, she developed recurrent acute gastrointestinal graft-versus-host disease and adenoviral hemorrhagic cystitis. Hence, the methylprednisolone (mPSL) dose was increased to 2 mg/kg, and mesenchymal stem cells were administered. Read More

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Influence of bisphosphonates on oral implantology: Sodium alendronate and zoledronic acid enhance the synthesis and activity of matrix metalloproteinases by gingival fibroblasts seeded on titanium.

Arch Oral Biol 2021 Jul 24;127:105134. Epub 2021 Apr 24.

Department of Physiology and Pathology, São Paulo State University (UNESP), School of Dentistry, Araraquara, SP, Brazil.

Objective: This study aimed to assess the influence of the bisphosphonates zoledronic acid and sodium alendronate on MMP-2 and MMP-9 synthesis and activity by gingival fibroblasts seeded onto titanium substrate.

Design: Titanium discs were placed in 24-well cell culture plates and gingival fibroblasts were seeded (1 × 10 cells/discs) on them using Dulbecco's Modified Eagle's Medium (DMEM) + 10 % fetal bovine serum (FBS) for 24 h. After this period, a fresh serum-free DMEM containing zoledronic acid or sodium alendronate at 0. Read More

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Palladium-catalyzed one-pot phosphorylation of phenols mediated by sulfuryl fluoride.

Chem Commun (Camb) 2021 May;57(37):4588-4591

Shanghai Institute for Advanced Immunochemical Studies, ShanghaiTech University, Shanghai, 201210, China.

We report a general palladium-catalyzed one-pot procedure for the synthesis of phosphonates, phosphinates and phosphine oxides from phenols mediated by sulfuryl fluoride. It features mild conditions, broad substrate scope, high functionality tolerance and water insensitivity. The utility of this procedure has been well demonstrated by gram-scale synthesis, sequential synthesis of click chemistry building blocks, late-stage decoration of drugs and natural products and on-DNA synthesis of phosphine oxide for a DNA-encoded library (DEL). Read More

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