Syntheses and preliminary biological studies of four meso-tetra[(nido-carboranylmethyl)phenyl]porphyrins

M. GraçaH Vicente, Benjamin F. Edwards, Shankar J. Shetty, Yongjin Hou, James E Boggan

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

Two meso-tetra[(nido-carboranylmethyl)phenyl]porphyrins (para- and meta-regioisomers) and their corresponding Zn(II) complexes have been synthesized with the aim of studying the effect of carborane distribution and metalation on the biological properties of this series of compounds. In vitro cell toxicity, uptake/efflux, and subcellular localization using rat 9L, mouse B16 and/or human U-373MG cells were evaluated. All four amphiphilic porphyrins display very low cytotoxicities and time- and concentration-dependent uptake by cells, which is influenced by serum proteins. Preliminary subcellular localization studies suggest that one of these compounds localizes in close proximity to the cell nucleus. All four nido-carboranylporphyrins show promise as boron-carriers for the boron neutron capture therapy of cancers, particularly the metal-free nido-carboranylporphyrins 5 and 12, which are able to deliver higher amount of boron to cells in vitro than the corresponding zinc complexes.

Original languageEnglish (US)
Pages (from-to)481-492
Number of pages12
JournalBioorganic and Medicinal Chemistry
Volume10
Issue number3
DOIs
StatePublished - 2002

Fingerprint

Boron
Porphyrins
Boron Neutron Capture Therapy
Cytotoxicity
Toxicity
Zinc
Rats
Blood Proteins
Neutrons
Metals
Cell Nucleus
Cells
Neoplasms
In Vitro Techniques

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Syntheses and preliminary biological studies of four meso-tetra[(nido-carboranylmethyl)phenyl]porphyrins. / Vicente, M. GraçaH; Edwards, Benjamin F.; Shetty, Shankar J.; Hou, Yongjin; Boggan, James E.

In: Bioorganic and Medicinal Chemistry, Vol. 10, No. 3, 2002, p. 481-492.

Research output: Contribution to journalArticle

Vicente, M. GraçaH ; Edwards, Benjamin F. ; Shetty, Shankar J. ; Hou, Yongjin ; Boggan, James E. / Syntheses and preliminary biological studies of four meso-tetra[(nido-carboranylmethyl)phenyl]porphyrins. In: Bioorganic and Medicinal Chemistry. 2002 ; Vol. 10, No. 3. pp. 481-492.
@article{6ce9ec6d9c404757936398c56f7b7384,
title = "Syntheses and preliminary biological studies of four meso-tetra[(nido-carboranylmethyl)phenyl]porphyrins",
abstract = "Two meso-tetra[(nido-carboranylmethyl)phenyl]porphyrins (para- and meta-regioisomers) and their corresponding Zn(II) complexes have been synthesized with the aim of studying the effect of carborane distribution and metalation on the biological properties of this series of compounds. In vitro cell toxicity, uptake/efflux, and subcellular localization using rat 9L, mouse B16 and/or human U-373MG cells were evaluated. All four amphiphilic porphyrins display very low cytotoxicities and time- and concentration-dependent uptake by cells, which is influenced by serum proteins. Preliminary subcellular localization studies suggest that one of these compounds localizes in close proximity to the cell nucleus. All four nido-carboranylporphyrins show promise as boron-carriers for the boron neutron capture therapy of cancers, particularly the metal-free nido-carboranylporphyrins 5 and 12, which are able to deliver higher amount of boron to cells in vitro than the corresponding zinc complexes.",
author = "Vicente, {M. Gra{\cc}aH} and Edwards, {Benjamin F.} and Shetty, {Shankar J.} and Yongjin Hou and Boggan, {James E}",
year = "2002",
doi = "10.1016/S0968-0896(01)00300-5",
language = "English (US)",
volume = "10",
pages = "481--492",
journal = "Bioorganic and Medicinal Chemistry",
issn = "0968-0896",
publisher = "Elsevier Limited",
number = "3",

}

TY - JOUR

T1 - Syntheses and preliminary biological studies of four meso-tetra[(nido-carboranylmethyl)phenyl]porphyrins

AU - Vicente, M. GraçaH

AU - Edwards, Benjamin F.

AU - Shetty, Shankar J.

AU - Hou, Yongjin

AU - Boggan, James E

PY - 2002

Y1 - 2002

N2 - Two meso-tetra[(nido-carboranylmethyl)phenyl]porphyrins (para- and meta-regioisomers) and their corresponding Zn(II) complexes have been synthesized with the aim of studying the effect of carborane distribution and metalation on the biological properties of this series of compounds. In vitro cell toxicity, uptake/efflux, and subcellular localization using rat 9L, mouse B16 and/or human U-373MG cells were evaluated. All four amphiphilic porphyrins display very low cytotoxicities and time- and concentration-dependent uptake by cells, which is influenced by serum proteins. Preliminary subcellular localization studies suggest that one of these compounds localizes in close proximity to the cell nucleus. All four nido-carboranylporphyrins show promise as boron-carriers for the boron neutron capture therapy of cancers, particularly the metal-free nido-carboranylporphyrins 5 and 12, which are able to deliver higher amount of boron to cells in vitro than the corresponding zinc complexes.

AB - Two meso-tetra[(nido-carboranylmethyl)phenyl]porphyrins (para- and meta-regioisomers) and their corresponding Zn(II) complexes have been synthesized with the aim of studying the effect of carborane distribution and metalation on the biological properties of this series of compounds. In vitro cell toxicity, uptake/efflux, and subcellular localization using rat 9L, mouse B16 and/or human U-373MG cells were evaluated. All four amphiphilic porphyrins display very low cytotoxicities and time- and concentration-dependent uptake by cells, which is influenced by serum proteins. Preliminary subcellular localization studies suggest that one of these compounds localizes in close proximity to the cell nucleus. All four nido-carboranylporphyrins show promise as boron-carriers for the boron neutron capture therapy of cancers, particularly the metal-free nido-carboranylporphyrins 5 and 12, which are able to deliver higher amount of boron to cells in vitro than the corresponding zinc complexes.

UR - http://www.scopus.com/inward/record.url?scp=0036157559&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0036157559&partnerID=8YFLogxK

U2 - 10.1016/S0968-0896(01)00300-5

DO - 10.1016/S0968-0896(01)00300-5

M3 - Article

C2 - 11814833

AN - SCOPUS:0036157559

VL - 10

SP - 481

EP - 492

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

IS - 3

ER -