Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications

Kaboudin, Babak; Daliri, Payam; Faghih, Samaneh; Esfandiari, Hesam

doi:10.3389/fchem.2022.890696

Cited by 17 publications

(10 citation statements)

References 87 publications

(87 reference statements)

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“…The first BTAs approved by the FDA for the treatment of bone metastases were bisphosphonates. Apart from the treatment of bone metastases, bisphosphonates are commonly applied in the therapy of osteoporosis and Paget’s disease [ 147 ]. Currently, they are also investigated as a potential treatment for otosclerosis, osteoarthritis of the knee, inflammatory rheumatic diseases, and many others diseases [ 148 , 149 , 150 ]…”

Section: Bone-targeted Agentsmentioning

confidence: 99%

Biological and Clinical Aspects of Metastatic Spinal Tumors

Litak

Czyżewski

Szymoniuk

et al. 2022

Cancers

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Spine metastases are a common life-threatening complication of advanced-stage malignancies and often result in poor prognosis. Symptomatic spine metastases develop in the course of about 10% of malignant neoplasms. Therefore, it is essential for contemporary medicine to understand metastatic processes in order to find appropriate, targeted therapeutic options. Thanks to continuous research, there appears more and more detailed knowledge about cancer and metastasis, but these transformations are extremely complicated, e.g., due to the complexity of reactions, the variety of places where they occur, or the participation of both tumor cells and host cells in these transitions. The right target points in tumor metastasis mechanisms are still being researched; that will help us in the proper diagnosis as well as in finding the right treatment. In this literature review, we described the current knowledge about the molecular pathways and biomarkers engaged in metastatic processes involving the spine. We also presented a current bone-targeted treatment for spine metastases and the emerging therapies targeting the discussed molecular mechanisms.

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Section: Bone-targeted Agentsmentioning

confidence: 99%

Biological and Clinical Aspects of Metastatic Spinal Tumors

Litak

Czyżewski

Szymoniuk

et al. 2022

Cancers

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“…They have a wide range of applications, such as in (pro)drugs in medicine, among others. The presence of strong P–C bonds also makes them resistant to hydrolysis, allowing their use in the treatment of disorders of the calcium metabolism and bone diseases [ 1 , 2 , 3 , 4 , 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

Interaction between [(η6-p-cym)M(H2O)3]2+ (MII = Ru, Os) or [(η5-Cp*)M(H2O)3]2+ (MIII = Rh, Ir) and Phosphonate Derivatives of Iminodiacetic Acid: A Solution Equilibrium and DFT Study

et al. 2023

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The pH-dependent binding strengths and modes of the organometallic [(η6-p-cym)M(H2O)3]2+ (MII = Ru, Os; p-cym = 1-methyl-4-isopropylbenzene) or [(η5-Cp*)M(H2O)3]2+ (MIII = Rh, Ir; Cp* = pentamethylcyclopentadienyl anion) cations towards iminodiacetic acid (H2Ida) and its biorelevant mono- and diphosphonate derivatives N-(phosphonomethyl)-glycine (H3IdaP) and iminodi(methylphosphonic acid) (H4Ida2P) was studied in an aqueous solution. The results showed that all three of the ligands form 1:1 complexes via the tridentate (O,N,O) donor set, for which the binding mode was further corroborated by the DFT method. Although with IdaP3− and Ida2P4− in mono- and bis-protonated species, where H+ might also be located at the non-coordinating N atom, the theoretical calculations revealed the protonation of the phosphonate group(s) and the tridentate coordination of the phosphonate ligands. The replacement of one carboxylate in Ida2− by a phosphonate group (IdaP3−) resulted in a significant increase in the stability of the metal complexes; however, this increase vanished with Ida2P4−, which was most likely due to some steric hindrance upon the coordination of the second large phosphonate group to form (5 + 5) joined chelates. In the phosphonate-containing systems, the neutral 1:1 complexes are the major species at pH 7.4 in the millimolar concentration range that is supported by both NMR and ESI-TOF-MS.

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“…L carnitine ( Figure 1 ). This modification confers greater solubility, stability, and potency ( Kaboudin et al, 2022 ). β-HPC was proposed for the treatment of metabolic syndrome because, in animal models, it reduced blood levels of insulin, triglycerides and cholesterol in the liver and serum ( Gómez-Solís et al, 2011 ; Reyes-Esparza et al, 2014 ; De la Cruz-Cordero et al, 2016 ).…”

Section: Introductionmentioning

confidence: 99%

Effect of β − hydroxy − γ -aminophosphonate (β − HPC) on the hydrolytic activity of Nocardia brasiliensis as determined by FT−IR spectrometry

et al. 2023

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The use of immunomodulatory and metabolic modulating drugs has been considered a better strategy to improve the efficacy of conventional treatments against pathogens and metabolic diseases. L-carnitine is relevant in fatty acid metabolism and energy production by β-oxidation, but it also has a beneficial therapeutic immunomodulatory effect. The β-hydroxy-γ-aminophosphonate (β-HPC) was developed, synthesized and studied in different pathologies as a more soluble and stable analog than L-carnitine, which has been studied in bacterial physiology and metabolism; therefore, we set out to investigate the direct effect of β-HPC on the metabolism of N. brasiliensis, which causes actinomycetoma in Mexico and is underdiagnosed. To analyze the effect of β-HPC on the metabolic capacity of the bacterium for the hydrolysis of substrate casein, L-tyrosine, egg yolk, and tween 80, Fourier transform infrared spectroscopy (FT-IR) was employed. It was found that β-HPC increases the metabolic activity of N. brasiliensis associated with increased growth and increased hydrolysis of the substrates tested. By the effect of β-HPC, it was observed that, in the hydrolysis of L-tyrosine, the aromatic ring and functional groups were degraded. At 1515 cm–1, any distinctive signal or peak for this amino acid was missing, almost disappearing at 839, 720, 647, and 550 cm–1. In casein, hydrolysis is enhanced in the substrate, which is evident by the presence of NH, OH, amide, and CO. In casein, hydrolysis is enhanced in the substrate, which is evident by the presence of NH, OH, amide, COO, and P = O signals, characteristic of amino acids, in addition to the increase of the amide I and II bands. In Tween 80 the H-C = and C = C signals disappear and the ether signals are concentrated, it was distinguished by the intense band at 1100 cm–1. Egg yolk showed a large accumulation of phosphate groups at 1071 cm–1, where phosvitin is located. FT-IR has served to demonstrate that β-HPC is a hydrolysis enhancer. Furthermore, by obtaining the spectrum of N. brasiliensis, we intend to use it as a quick comparison tool with other spectra related to actinobacteria. Eventually, FT-IR may serve as a species identification option.

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Hydroxy- and Amino-Phosphonates and -Bisphosphonates: Synthetic Methods and Their Biological Applications

Cited by 17 publications

References 87 publications

Biological and Clinical Aspects of Metastatic Spinal Tumors

Biological and Clinical Aspects of Metastatic Spinal Tumors

Interaction between [(η6-p-cym)M(H2O)3]2+ (MII = Ru, Os) or [(η5-Cp*)M(H2O)3]2+ (MIII = Rh, Ir) and Phosphonate Derivatives of Iminodiacetic Acid: A Solution Equilibrium and DFT Study

Effect of β − hydroxy − γ -aminophosphonate (β − HPC) on the hydrolytic activity of Nocardia brasiliensis as determined by FT−IR spectrometry

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