Novel Multiple Type Molecular Targeted Antitumor Agents: Preparation and Preclinical Evaluation of Low-Molecular-Weight Phospha Sugar Derivatives

Makita, Reiko; Yamashita, Mitsuji; Yamaoka, Mayumi; Fujie, Manabu; Nakamura, Shuichi; Oshikawa, Tatsuo; Yamashita, Junko; Yamada, Manabu; Asai, Kazuhide; Suyama, Takuya; Kondo, Mitsuru; Hasegawa, Hiroko; Okita, Yoshimitsu; Hirakawa, Kazuhiko; Toda, Mitsuo; Ohnishi, Kazunori; Sugimura, Haruhiko

doi:10.1080/10426507.2014.993758

Cited by 3 publications

(1 citation statement)

References 26 publications

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“…Some phosphorus heterocycles that are being referred to as phospha‐sugars do not contain hydroxyl substituents on the cyclic skeleton and thus are not really carbohydrate analogues in a strict sense. In recent years, however, some of these phosphorus heterocycles have been synthesized and reported for applications as anticancer agents …”

Section: Endocyclic Oxygen Replacementmentioning

confidence: 99%

Design and synthesis of glycomimetics: Recent advances

Tamburrini

Colombo

Bernardi

2019

Medicinal Research Reviews

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In the past few decades, our understanding of glycan information‐encoding power has notably increased, thus leading to a significant growth also in the design and synthesis of glycomimetic probes. Combining data from multiple analytical sources, such as crystallography, nuclear magnetic resonance spectroscopy, and other biophysical methods (eg, surface plasmon resonance and carbohydrate microarrays) has allowed to shed light on the key interaction events between carbohydrates and their protein‐targets. However, the low metabolic stability of carbohydrates and their high hydrophilicity, which translates in low bioavailability, undermine their development as drugs. In this framework, the design of chemically modified analogues (called carbohydrate mimics or glycomimetics) appears as a valid alternative for the development of therapeutic agents. Glycomimetics, as structural and functional mimics of carbohydrates, can replace the native ligands in the interaction with target proteins, but are designed to show enhanced enzymatic stability and bioavailability and, possibly, an improved affinity and selectivity toward the target. In the present account, we specifically focus on the most recent advances in the design and synthesis of glycomimetics. In particular, we highlight the efforts of the scientific community in the development of straightforward synthetic procedures for the preparation of sugar mimics and in their preliminary biological evaluation.

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Section: Endocyclic Oxygen Replacementmentioning

confidence: 99%

Design and synthesis of glycomimetics: Recent advances

Tamburrini

Colombo

Bernardi

2019

Medicinal Research Reviews

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Analysis of Carbohydrates and Glycoconjugates by Matrix‐assisted Laser Desorption/Ionization Mass Spectrometry: An Update for 2015–2016

Harvey

2021

Mass Spectrometry Reviews

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This review is the ninth update of the original article published in 1999 on the application of matrix‐assisted laser desorption/ionization (MALDI) mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2016. Also included are papers that describe methods appropriate to analysis by MALDI, such as sample preparation techniques, even though the ionization method is not MALDI. Topics covered in the first part of the review include general aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, fragmentation and arrays. The second part of the review is devoted to applications to various structural types such as oligo‐ and poly‐saccharides, glycoproteins, glycolipids, glycosides and biopharmaceuticals. Much of this material is presented in tabular form. The third part of the review covers medical and industrial applications of the technique, studies of enzyme reactions and applications to chemical synthesis. The reported work shows increasing use of combined new techniques such as ion mobility and the enormous impact that MALDI imaging is having. MALDI, although invented over 30 years ago is still an ideal technique for carbohydrate analysis and advancements in the technique and range of applications show no sign of deminishing. © 2020 Wiley Periodicals, Inc.

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Ultraviolet-Light-Induced P–H Insertion of α-Halocarbenes

Liu,

Zhang,

et al. 2024

Org. Lett.

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An intriguing P−H insertion of arylhalodiazirines with H-phosphorus oxides under ultraviolet-light irradiation is described. This methodology provides an efficient and straightforward route to the construction of a variety of α-halophosphorus oxides in good yields (≤95%), which represents a unique example of P−H insertion of α-halocarbenes for C−P bond formation. The metal-free protocol features the advantages of mild reaction conditions, high atom economy, and environmental friendliness.

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Novel Multiple Type Molecular Targeted Antitumor Agents: Preparation and Preclinical Evaluation of Low-Molecular-Weight Phospha Sugar Derivatives

Cited by 3 publications

References 26 publications

Design and synthesis of glycomimetics: Recent advances

Design and synthesis of glycomimetics: Recent advances

Analysis of Carbohydrates and Glycoconjugates by Matrix‐assisted Laser Desorption/Ionization Mass Spectrometry: An Update for 2015–2016

Ultraviolet-Light-Induced P–H Insertion of α-Halocarbenes

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