Synthesis of dendritic bisphosphonates as bone targeting ligands

Kazuma Shimoda; Takahiro Mitsuoka; Kenta Ueda; Hiroshi Suemune; Go Hirai; Mariko Aso

doi:10.1016/j.tetlet.2018.11.028

Synthesis of dendritic bisphosphonates as bone targeting ligands

Kazuma Shimoda, Takahiro Mitsuoka, Kenta Ueda, Hiroshi Suemune, Go Hirai, Mariko Aso

Chemo-Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

A dendritic bisphosphonate carrying three bisphosphonate (BP) units in close proximity was designed as a ligand to conjugate large therapeutic molecules for their bone selective delivery. The Bu₃P-catalyzed conjugate addition of nitromethane to vinylidene bisphosphonate was effective to construct a quaternary carbon center carrying BP units. Owing to multivalent interactions, the dendritic bisphosphonate showed considerable affinity for the bone mineral hydroxyapatite even in the presence of a competitor, demonstrating potential as a bone targeting ligand.

Original language	English
Pages (from-to)	4528-4531
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2018.11.028
Publication status	Published - Dec 19 2018

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2018.11.028

Cite this

@article{dbee6080565a4265b4f0908e656f6474,

title = "Synthesis of dendritic bisphosphonates as bone targeting ligands",

abstract = "A dendritic bisphosphonate carrying three bisphosphonate (BP) units in close proximity was designed as a ligand to conjugate large therapeutic molecules for their bone selective delivery. The Bu3P-catalyzed conjugate addition of nitromethane to vinylidene bisphosphonate was effective to construct a quaternary carbon center carrying BP units. Owing to multivalent interactions, the dendritic bisphosphonate showed considerable affinity for the bone mineral hydroxyapatite even in the presence of a competitor, demonstrating potential as a bone targeting ligand.",

author = "Kazuma Shimoda and Takahiro Mitsuoka and Kenta Ueda and Hiroshi Suemune and Go Hirai and Mariko Aso",

note = "Funding Information: Funding from Japan Osteoporosis Foundation (JOF) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = dec,

day = "19",

doi = "10.1016/j.tetlet.2018.11.028",

language = "English",

volume = "59",

pages = "4528--4531",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "51",

}

TY - JOUR

T1 - Synthesis of dendritic bisphosphonates as bone targeting ligands

AU - Shimoda, Kazuma

AU - Mitsuoka, Takahiro

AU - Ueda, Kenta

AU - Suemune, Hiroshi

AU - Hirai, Go

AU - Aso, Mariko

PY - 2018/12/19

Y1 - 2018/12/19

N2 - A dendritic bisphosphonate carrying three bisphosphonate (BP) units in close proximity was designed as a ligand to conjugate large therapeutic molecules for their bone selective delivery. The Bu3P-catalyzed conjugate addition of nitromethane to vinylidene bisphosphonate was effective to construct a quaternary carbon center carrying BP units. Owing to multivalent interactions, the dendritic bisphosphonate showed considerable affinity for the bone mineral hydroxyapatite even in the presence of a competitor, demonstrating potential as a bone targeting ligand.

AB - A dendritic bisphosphonate carrying three bisphosphonate (BP) units in close proximity was designed as a ligand to conjugate large therapeutic molecules for their bone selective delivery. The Bu3P-catalyzed conjugate addition of nitromethane to vinylidene bisphosphonate was effective to construct a quaternary carbon center carrying BP units. Owing to multivalent interactions, the dendritic bisphosphonate showed considerable affinity for the bone mineral hydroxyapatite even in the presence of a competitor, demonstrating potential as a bone targeting ligand.

UR - http://www.scopus.com/inward/record.url?scp=85056754746&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85056754746&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2018.11.028

DO - 10.1016/j.tetlet.2018.11.028

M3 - Article

AN - SCOPUS:85056754746

SN - 0040-4039

VL - 59

SP - 4528

EP - 4531

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

Synthesis of dendritic bisphosphonates as bone targeting ligands

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this