Literature DB >> 35061200

Water-soluble BODIPY-nido-carborane nanoparticles applied to biocompatibility tumor cell imaging.

Dongfang Dai1, Guangchang Lian2, Xia He1, Jifeng Feng1, Guofan Jin3.   

Abstract

In this article, o-carborane has a high boron content, high hydrophobicity, and good chemical stability. It has been widely used in the fields of biology and medicine, especially in the application of boron neutron capture therapy (BNCT). However, o-carborane is a fat-soluble compound, its hydrophobicity is too strong, and its bioavailability is poor. This project aims to improve the water solubility of o-carborane drugs, so that the drugs can reach specific sites. For this reason, this article provides a one-pot reaction for the synthesis of water-soluble boron-containing drugs. 2-Chloro-1-(difluoroboranyl)-5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)(phenyl) methyl)-1H-pyrrole and ethylenediamine are used as raw materials to synthesize fluorescent molecular probe BODIPY-NH2, and the fluorescent molecular probe is reacted with P-CBMA (poly(carboxybetaine methacrylate)) to produce a water-soluble gel polymer. Water-soluble o-carborane polymers were synthesized by hydrogen bonding of the polymers with bis(4-azaspiro[3.4]octan-4-ium)-nido-ortho-carborane and bis(5-azaspiro[4.5]decan-5-ium)-nido-ortho-caborane. The two polymers were characterized and the results showed that the maximum UV absorption wavelength of the two boron polymers in different polar solutions was 530-540 nm. In the fluorescence spectrum, the maximum emission wavelengths of the two boron polymers are concentrated between 550 and 560 nm. Through electron microscopy imaging, the fluoroboron pyrrole polymers wrap the boron clusters to form a spherical stacked. Through fluorescent cell imaging, both boron polymers can enter target cells.
© 2022. The Author(s), under exclusive licence to European Photochemistry Association, European Society for Photobiology.

Entities:  

Keywords:  BNCT; BODIPY; Biocompatibility; Carborane; Fluorescence

Mesh:

Substances:

Year:  2022        PMID: 35061200     DOI: 10.1007/s43630-021-00148-1

Source DB:  PubMed          Journal:  Photochem Photobiol Sci        ISSN: 1474-905X            Impact factor:   3.982


  11 in total

1.  Nuclear Theranostics in Taiwan.

Authors:  Ko-Han Lin; Yi-Wei Chen; Rheun-Chuan Lee; Ling-Wei Wang; Fong-In Chou; Chi-Wei Chang; Sang-Hue Yen; Wen-Sheng Huang
Journal:  Nucl Med Mol Imaging       Date:  2019-02-01

2.  Structure-activity relationship for aryl and heteroaryl boronic acid inhibitors of hormone-sensitive lipase.

Authors:  Søren Ebdrup; Poul Jacobsen; Anupma Dhanda Farrington; Per Vedsø
Journal:  Bioorg Med Chem       Date:  2005-03-15       Impact factor: 3.641

3.  A multiple acetal chalcone-BODIPY-based fluorescence: synthesis, physical property, and biological studies.

Authors:  Yuling Wang; Fuyan Xiao; Tingyu Shao; Kaibo Hu; Guangchang Lian; Jiankang Feng; Hao Chen; Guofan Jin
Journal:  Anal Bioanal Chem       Date:  2021-03-12       Impact factor: 4.142

4.  Penetration of brain and brain tumor. VII. Tumor-binding sulfhydryl boron compounds.

Authors:  A H Soloway; H Hatanaka; M A Davis
Journal:  J Med Chem       Date:  1967-07       Impact factor: 7.446

5.  Uptake of a boronated epidermal growth factor-dextran conjugate in CHO xenografts with and without human EGF-receptor expression.

Authors:  P Olsson; L Gedda; H Goike; L Liu; V P Collins; J Pontén; J Carlsson
Journal:  Anticancer Drug Des       Date:  1998-06

6.  The properties of substituted 3D-aromatic neutral carboranes: the potential for σ-hole bonding.

Authors:  Rabindranath Lo; Jindřich Fanfrlík; Martin Lepšík; Pavel Hobza
Journal:  Phys Chem Chem Phys       Date:  2015-07-27       Impact factor: 3.676

Review 7.  A critical assessment of boron target compounds for boron neutron capture therapy.

Authors:  M Frederick Hawthorne; Mark W Lee
Journal:  J Neurooncol       Date:  2003 Mar-Apr       Impact factor: 4.130

8.  Novel carboranyl amino acids and peptides: reagents for antibody modification and subsequent neutron-capture studies.

Authors:  A Varadarajan; M F Hawthorne
Journal:  Bioconjug Chem       Date:  1991 Jul-Aug       Impact factor: 4.774

9.  π aromaticity and three-dimensional aromaticity: two sides of the same coin?

Authors:  Jordi Poater; Miquel Solà; Clara Viñas; Francesc Teixidor
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-15       Impact factor: 15.336

Review 10.  Boron Neutron Capture Therapy: A Review of Clinical Applications.

Authors:  Timothy D Malouff; Danushka S Seneviratne; Daniel K Ebner; William C Stross; Mark R Waddle; Daniel M Trifiletti; Sunil Krishnan
Journal:  Front Oncol       Date:  2021-02-26       Impact factor: 6.244

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