Synthesis of decacationic [60]fullerene decaiodides giving photoinduced production of superoxide radicals and effective PDT-mediation on antimicrobial photoinactivation

Min Wang; Satyanarayana Maragani; Liyi Huang; Seaho Jeon; Taizoon Canteenwala; Michael R. Hamblin; Long Y. Chiang

doi:10.1016/j.ejmech.2013.01.052

Synthesis of decacationic [60]fullerene decaiodides giving photoinduced production of superoxide radicals and effective PDT-mediation on antimicrobial photoinactivation

Min Wang, Satyanarayana Maragani, Liyi Huang, Seaho Jeon, Taizoon Canteenwala, Michael R. Hamblin, Long Y. Chiang

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

43 Citations (Scopus)

Abstract

We report a novel class of highly water-soluble decacationic methano[60]fullerene decaiodides C₆₀[>M(C₃N ₆⁺C₃)₂]-(I^-) ₁₀ [1-(I^-)₁₀] capable of co-producing singlet oxygen (Type-II) and highly reactive hydroxyl radicals, formed from superoxide radicals in Type-I photosensitizing reactions, upon illumination at both UVA and white light wavelengths. The O₂^-·-production efficiency of 1-(I^-)₁₀ was confirmed by using an O ₂^-·-reactive bis(2,4-dinitrobenzenesulfonyl) tetrafluorofluorescein probe and correlated to the photoinduced electron-transfer event going from iodide anions to ³C ₆₀*[>M(C₃N₆⁺C ₃)₂] leading to C₆₀ ^-·[>M(C₃N₆⁺C ₃)₂]. Incorporation of a defined number (ten) of quaternary ammonium cationic charges per C₆₀ in 1 was aimed to enhance its ability to target pathogenic Gram-positive and Gram-negative bacterial cells. We used the well-characterized malonato[60]fullerene diester monoadduct C₆₀[>M(t-Bu)₂] as the starting fullerene derivative to provide a better synthetic route to C₆₀[>M(C ₃N₆⁺C₃)₂] via transesterification reaction under trifluoroacetic acid catalyzed conditions. These compounds may be used as effective photosensitizers and nano-PDT drugs for photoinactivation of pathogens.

Original language	English
Pages (from-to)	170-184
Number of pages	15
Journal	European Journal of Medicinal Chemistry
Volume	63
DOIs	https://doi.org/10.1016/j.ejmech.2013.01.052
Publication status	Published - 2013
Externally published	Yes

Keywords

Antimicrobial photodynamic therapy
Decacationic C monoadducts
Di(N,N′,N,N,N,N-hexapropyl-hexa(aminoethyl)amido) malonate arm
Photoinduced radicals
Photosensitizer
Transesterification

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

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10.1016/j.ejmech.2013.01.052

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Wang, M., Maragani, S., Huang, L., Jeon, S., Canteenwala, T., Hamblin, M. R., & Chiang, L. Y. (2013). Synthesis of decacationic [60]fullerene decaiodides giving photoinduced production of superoxide radicals and effective PDT-mediation on antimicrobial photoinactivation. European Journal of Medicinal Chemistry, 63, 170-184. https://doi.org/10.1016/j.ejmech.2013.01.052

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title = "Synthesis of decacationic [60]fullerene decaiodides giving photoinduced production of superoxide radicals and effective PDT-mediation on antimicrobial photoinactivation",

abstract = "We report a novel class of highly water-soluble decacationic methano[60]fullerene decaiodides C60[>M(C3N 6+C3)2]-(I-) 10 [1-(I-)10] capable of co-producing singlet oxygen (Type-II) and highly reactive hydroxyl radicals, formed from superoxide radicals in Type-I photosensitizing reactions, upon illumination at both UVA and white light wavelengths. The O2-·-production efficiency of 1-(I-)10 was confirmed by using an O 2-·-reactive bis(2,4-dinitrobenzenesulfonyl) tetrafluorofluorescein probe and correlated to the photoinduced electron-transfer event going from iodide anions to 3C 60*[>M(C3N6+C 3)2] leading to C60 -·[>M(C3N6+C 3)2]. Incorporation of a defined number (ten) of quaternary ammonium cationic charges per C60 in 1 was aimed to enhance its ability to target pathogenic Gram-positive and Gram-negative bacterial cells. We used the well-characterized malonato[60]fullerene diester monoadduct C60[>M(t-Bu)2] as the starting fullerene derivative to provide a better synthetic route to C60[>M(C 3N6+C3)2] via transesterification reaction under trifluoroacetic acid catalyzed conditions. These compounds may be used as effective photosensitizers and nano-PDT drugs for photoinactivation of pathogens.",

keywords = "Antimicrobial photodynamic therapy, Decacationic C monoadducts, Di(N,N′,N,N,N,N-hexapropyl-hexa(aminoethyl)amido) malonate arm, Photoinduced radicals, Photosensitizer, Transesterification",

author = "Min Wang and Satyanarayana Maragani and Liyi Huang and Seaho Jeon and Taizoon Canteenwala and Hamblin, {Michael R.} and Chiang, {Long Y.}",

year = "2013",

doi = "10.1016/j.ejmech.2013.01.052",

language = "English",

volume = "63",

pages = "170--184",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

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TY - JOUR

T1 - Synthesis of decacationic [60]fullerene decaiodides giving photoinduced production of superoxide radicals and effective PDT-mediation on antimicrobial photoinactivation

AU - Wang, Min

AU - Maragani, Satyanarayana

AU - Huang, Liyi

AU - Jeon, Seaho

AU - Canteenwala, Taizoon

AU - Hamblin, Michael R.

AU - Chiang, Long Y.

PY - 2013

Y1 - 2013

N2 - We report a novel class of highly water-soluble decacationic methano[60]fullerene decaiodides C60[>M(C3N 6+C3)2]-(I-) 10 [1-(I-)10] capable of co-producing singlet oxygen (Type-II) and highly reactive hydroxyl radicals, formed from superoxide radicals in Type-I photosensitizing reactions, upon illumination at both UVA and white light wavelengths. The O2-·-production efficiency of 1-(I-)10 was confirmed by using an O 2-·-reactive bis(2,4-dinitrobenzenesulfonyl) tetrafluorofluorescein probe and correlated to the photoinduced electron-transfer event going from iodide anions to 3C 60*[>M(C3N6+C 3)2] leading to C60 -·[>M(C3N6+C 3)2]. Incorporation of a defined number (ten) of quaternary ammonium cationic charges per C60 in 1 was aimed to enhance its ability to target pathogenic Gram-positive and Gram-negative bacterial cells. We used the well-characterized malonato[60]fullerene diester monoadduct C60[>M(t-Bu)2] as the starting fullerene derivative to provide a better synthetic route to C60[>M(C 3N6+C3)2] via transesterification reaction under trifluoroacetic acid catalyzed conditions. These compounds may be used as effective photosensitizers and nano-PDT drugs for photoinactivation of pathogens.

AB - We report a novel class of highly water-soluble decacationic methano[60]fullerene decaiodides C60[>M(C3N 6+C3)2]-(I-) 10 [1-(I-)10] capable of co-producing singlet oxygen (Type-II) and highly reactive hydroxyl radicals, formed from superoxide radicals in Type-I photosensitizing reactions, upon illumination at both UVA and white light wavelengths. The O2-·-production efficiency of 1-(I-)10 was confirmed by using an O 2-·-reactive bis(2,4-dinitrobenzenesulfonyl) tetrafluorofluorescein probe and correlated to the photoinduced electron-transfer event going from iodide anions to 3C 60*[>M(C3N6+C 3)2] leading to C60 -·[>M(C3N6+C 3)2]. Incorporation of a defined number (ten) of quaternary ammonium cationic charges per C60 in 1 was aimed to enhance its ability to target pathogenic Gram-positive and Gram-negative bacterial cells. We used the well-characterized malonato[60]fullerene diester monoadduct C60[>M(t-Bu)2] as the starting fullerene derivative to provide a better synthetic route to C60[>M(C 3N6+C3)2] via transesterification reaction under trifluoroacetic acid catalyzed conditions. These compounds may be used as effective photosensitizers and nano-PDT drugs for photoinactivation of pathogens.

KW - Antimicrobial photodynamic therapy

KW - Decacationic C monoadducts

KW - Di(N,N′,N,N,N,N-hexapropyl-hexa(aminoethyl)amido) malonate arm

KW - Photoinduced radicals

KW - Photosensitizer

KW - Transesterification

UR - http://www.scopus.com/inward/record.url?scp=84874618460&partnerID=8YFLogxK

U2 - 10.1016/j.ejmech.2013.01.052

DO - 10.1016/j.ejmech.2013.01.052

M3 - Article

C2 - 23474903

AN - SCOPUS:84874618460

SN - 0223-5234

VL - 63

SP - 170

EP - 184

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

ER -

Synthesis of decacationic [60]fullerene decaiodides giving photoinduced production of superoxide radicals and effective PDT-mediation on antimicrobial photoinactivation

Abstract

Keywords

ASJC Scopus subject areas

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