Imidazole metalloporphyrins as photosensitizers for photodynamic therapy: Role of molecular charge, central metal and hydroxyl radical production

Pawel Mroz; Jayeeta Bhaumik; Dilek K. Dogutan; Zarmeneh Aly; Zahra Kamal; Laiqua Khalid; Hooi Ling Kee; David F. Bocian; Dewey Holten; Jonathan S. Lindsey; Michael R. Hamblin

doi:10.1016/j.canlet.2009.02.054

Imidazole metalloporphyrins as photosensitizers for photodynamic therapy: Role of molecular charge, central metal and hydroxyl radical production

Pawel Mroz, Jayeeta Bhaumik, Dilek K. Dogutan, Zarmeneh Aly, Zahra Kamal, Laiqua Khalid, Hooi Ling Kee, David F. Bocian, Dewey Holten, Jonathan S. Lindsey, Michael R. Hamblin

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

115 Scopus citations

Abstract

The in vitro photodynamic therapy activity of four imidazole-substituted metalloporphyrins has been studied using human (HeLa) and mouse (CT26) cancer cell lines: an anionic Zn porphyrin and a homologous series of three cationic Zn, Pd or InCl porphyrins. A dramatic difference in phototoxicity was found: Pd cationic > InCl cationic > Zn cationic > Zn anionic. HeLa cells were more susceptible than CT26 cells. Induction of apoptosis was demonstrated using a fluorescent caspase assay. The anionic Zn porphyrin localized in lysosomes while the cationic Zn porphyrin localized in lysosomes and mitochondria, as assessed by fluorescence microscopy. Studies using fluorescent probes suggested that the cationic Pd porphyrin produced more hydroxyl radicals as the reactive oxygen species. Thus, the cationic Pd porphyrin has high potential as a photosensitizer and gives insights into characteristics for improved molecular designs.

Original language	English (US)
Pages (from-to)	63-76
Number of pages	14
Journal	Cancer Letters
Volume	282
Issue number	1
DOIs	https://doi.org/10.1016/j.canlet.2009.02.054
State	Published - Sep 8 2009
Externally published	Yes

Bibliographical note

Funding Information:
Work at Wellman Center for Photomedicine was funded by NIH-CA/AI838801 to MRH. Work at NCSU was supported by NIH-GM36238 to JSL. HLK was funded by the Imaging Sciences Pathway training grant from the NIH (5T90 DA022871) at Washington University.

Keywords

Apoptosis
Fluorescence microscopy
Hydroxyl radicals
Metalloporphyrins
Photophysics
Phototoxicity
Reactive oxygen species
Structure function relationship

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Publisher link

10.1016/j.canlet.2009.02.054

Find It

Find It at U of M Libraries

Cite this

Mroz, P., Bhaumik, J., Dogutan, D. K., Aly, Z., Kamal, Z., Khalid, L., Kee, H. L., Bocian, D. F., Holten, D., Lindsey, J. S., & Hamblin, M. R. (2009). Imidazole metalloporphyrins as photosensitizers for photodynamic therapy: Role of molecular charge, central metal and hydroxyl radical production. Cancer Letters, 282(1), 63-76. https://doi.org/10.1016/j.canlet.2009.02.054

@article{528d70b3d5ab4231a048c21a07a89dca,

title = "Imidazole metalloporphyrins as photosensitizers for photodynamic therapy: Role of molecular charge, central metal and hydroxyl radical production",

abstract = "The in vitro photodynamic therapy activity of four imidazole-substituted metalloporphyrins has been studied using human (HeLa) and mouse (CT26) cancer cell lines: an anionic Zn porphyrin and a homologous series of three cationic Zn, Pd or InCl porphyrins. A dramatic difference in phototoxicity was found: Pd cationic > InCl cationic > Zn cationic > Zn anionic. HeLa cells were more susceptible than CT26 cells. Induction of apoptosis was demonstrated using a fluorescent caspase assay. The anionic Zn porphyrin localized in lysosomes while the cationic Zn porphyrin localized in lysosomes and mitochondria, as assessed by fluorescence microscopy. Studies using fluorescent probes suggested that the cationic Pd porphyrin produced more hydroxyl radicals as the reactive oxygen species. Thus, the cationic Pd porphyrin has high potential as a photosensitizer and gives insights into characteristics for improved molecular designs.",

keywords = "Apoptosis, Fluorescence microscopy, Hydroxyl radicals, Metalloporphyrins, Photophysics, Phototoxicity, Reactive oxygen species, Structure function relationship",

author = "Pawel Mroz and Jayeeta Bhaumik and Dogutan, {Dilek K.} and Zarmeneh Aly and Zahra Kamal and Laiqua Khalid and Kee, {Hooi Ling} and Bocian, {David F.} and Dewey Holten and Lindsey, {Jonathan S.} and Hamblin, {Michael R.}",

note = "Funding Information: Work at Wellman Center for Photomedicine was funded by NIH-CA/AI838801 to MRH. Work at NCSU was supported by NIH-GM36238 to JSL. HLK was funded by the Imaging Sciences Pathway training grant from the NIH (5T90 DA022871) at Washington University. ",

year = "2009",

month = sep,

day = "8",

doi = "10.1016/j.canlet.2009.02.054",

language = "English (US)",

volume = "282",

pages = "63--76",

journal = "Cancer Letters",

issn = "0304-3835",

publisher = "Elsevier Ireland Ltd",

number = "1",

}

TY - JOUR

T1 - Imidazole metalloporphyrins as photosensitizers for photodynamic therapy

T2 - Role of molecular charge, central metal and hydroxyl radical production

AU - Mroz, Pawel

AU - Bhaumik, Jayeeta

AU - Dogutan, Dilek K.

AU - Aly, Zarmeneh

AU - Kamal, Zahra

AU - Khalid, Laiqua

AU - Kee, Hooi Ling

AU - Bocian, David F.

AU - Holten, Dewey

AU - Lindsey, Jonathan S.

AU - Hamblin, Michael R.

N1 - Funding Information: Work at Wellman Center for Photomedicine was funded by NIH-CA/AI838801 to MRH. Work at NCSU was supported by NIH-GM36238 to JSL. HLK was funded by the Imaging Sciences Pathway training grant from the NIH (5T90 DA022871) at Washington University.

PY - 2009/9/8

Y1 - 2009/9/8

N2 - The in vitro photodynamic therapy activity of four imidazole-substituted metalloporphyrins has been studied using human (HeLa) and mouse (CT26) cancer cell lines: an anionic Zn porphyrin and a homologous series of three cationic Zn, Pd or InCl porphyrins. A dramatic difference in phototoxicity was found: Pd cationic > InCl cationic > Zn cationic > Zn anionic. HeLa cells were more susceptible than CT26 cells. Induction of apoptosis was demonstrated using a fluorescent caspase assay. The anionic Zn porphyrin localized in lysosomes while the cationic Zn porphyrin localized in lysosomes and mitochondria, as assessed by fluorescence microscopy. Studies using fluorescent probes suggested that the cationic Pd porphyrin produced more hydroxyl radicals as the reactive oxygen species. Thus, the cationic Pd porphyrin has high potential as a photosensitizer and gives insights into characteristics for improved molecular designs.

AB - The in vitro photodynamic therapy activity of four imidazole-substituted metalloporphyrins has been studied using human (HeLa) and mouse (CT26) cancer cell lines: an anionic Zn porphyrin and a homologous series of three cationic Zn, Pd or InCl porphyrins. A dramatic difference in phototoxicity was found: Pd cationic > InCl cationic > Zn cationic > Zn anionic. HeLa cells were more susceptible than CT26 cells. Induction of apoptosis was demonstrated using a fluorescent caspase assay. The anionic Zn porphyrin localized in lysosomes while the cationic Zn porphyrin localized in lysosomes and mitochondria, as assessed by fluorescence microscopy. Studies using fluorescent probes suggested that the cationic Pd porphyrin produced more hydroxyl radicals as the reactive oxygen species. Thus, the cationic Pd porphyrin has high potential as a photosensitizer and gives insights into characteristics for improved molecular designs.

KW - Apoptosis

KW - Fluorescence microscopy

KW - Hydroxyl radicals

KW - Metalloporphyrins

KW - Photophysics

KW - Phototoxicity

KW - Reactive oxygen species

KW - Structure function relationship

UR - http://www.scopus.com/inward/record.url?scp=67649395577&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=67649395577&partnerID=8YFLogxK

U2 - 10.1016/j.canlet.2009.02.054

DO - 10.1016/j.canlet.2009.02.054

M3 - Article

C2 - 19346065

AN - SCOPUS:67649395577

SN - 0304-3835

VL - 282

SP - 63

EP - 76

JO - Cancer Letters

JF - Cancer Letters

IS - 1

ER -

Imidazole metalloporphyrins as photosensitizers for photodynamic therapy: Role of molecular charge, central metal and hydroxyl radical production

Abstract

Bibliographical note

Keywords

UN SDGs

Publisher link

Find It

Other files and links

Fingerprint

Cite this