Synthesis and photodynamic effect of new highly photostable decacationically armed [60]- and [70]fullerene decaiodide monoadducts to target pathogenic bacteria and cancer cells

Min Wang; Liyi Huang; Sulbha K. Sharma; Seaho Jeon; Sammaiah Thota; Felipe F. Sperandio; Suhasini Nayka; Julie Chang; Michael R. Hamblin; Long Y. Chiang

doi:10.1021/jm3000664

Synthesis and photodynamic effect of new highly photostable decacationically armed [60]- and [70]fullerene decaiodide monoadducts to target pathogenic bacteria and cancer cells

Min Wang, Liyi Huang, Sulbha K. Sharma, Seaho Jeon, Sammaiah Thota, Felipe F. Sperandio, Suhasini Nayka, Julie Chang, Michael R. Hamblin, Long Y. Chiang

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

56 Citations (Scopus)

Abstract

Novel water-soluble decacationically armed C ₆₀ and C ₇₀ decaiodide monoadducts, C ₆₀- and C ₇₀[> M(C ₃N ₆ ⁺C ₃) ₂], were synthesized, characterized, and applied as photosensitizers and potential nano-PDT agents against pathogenic bacteria and cancer cells. A high number of cationic charges per fullerene cage and H-bonding moieties were designed for rapid binding to the anionic residues displayed on the outer parts of bacterial cell walls. In the presence of a high number of electron-donating iodide anions as parts of quaternary ammonium salts in the arm region, we found that C ₇₀[>M(C ₃N ₆ ⁺C ₃) ₂] produced more HO ^"¢ than C ₆₀[> M(C ₃N ₆ ⁺C ₃) ₂], in addition to ¹O ₂. This finding offers an explanation of the preferential killing of Gram-positive and Gram-negative bacteria by C ₆₀[>M(C ₃N ₆ ⁺C ₃) ₂] and C ₇₀[>M(C ₃N ₆ ⁺C ₃) ₂], respectively. The hypothesis is that ¹O ₂ can diffuse more easily into porous cell walls of Gram-positive bacteria to reach sensitive sites, while the less permeable Gram-negative bacterial cell wall needs the more reactive HO ^"¢ to cause real damage.

Original language	English
Pages (from-to)	4274-4285
Number of pages	12
Journal	Journal of Medicinal Chemistry
Volume	55
Issue number	9
DOIs	https://doi.org/10.1021/jm3000664
Publication status	Published - 10 May 2012
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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10.1021/jm3000664

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Wang, M., Huang, L., Sharma, S. K., Jeon, S., Thota, S., Sperandio, F. F., Nayka, S., Chang, J., Hamblin, M. R., & Chiang, L. Y. (2012). Synthesis and photodynamic effect of new highly photostable decacationically armed [60]- and [70]fullerene decaiodide monoadducts to target pathogenic bacteria and cancer cells. Journal of Medicinal Chemistry, 55(9), 4274-4285. https://doi.org/10.1021/jm3000664

@article{126c3ce041854c56b36f5cc3eda46f74,

title = "Synthesis and photodynamic effect of new highly photostable decacationically armed [60]- and [70]fullerene decaiodide monoadducts to target pathogenic bacteria and cancer cells",

abstract = "Novel water-soluble decacationically armed C 60 and C 70 decaiodide monoadducts, C 60- and C 70[> M(C 3N 6 +C 3) 2], were synthesized, characterized, and applied as photosensitizers and potential nano-PDT agents against pathogenic bacteria and cancer cells. A high number of cationic charges per fullerene cage and H-bonding moieties were designed for rapid binding to the anionic residues displayed on the outer parts of bacterial cell walls. In the presence of a high number of electron-donating iodide anions as parts of quaternary ammonium salts in the arm region, we found that C 70[>M(C 3N 6 +C 3) 2] produced more HO {"}¢ than C 60[> M(C 3N 6 +C 3) 2], in addition to 1O 2. This finding offers an explanation of the preferential killing of Gram-positive and Gram-negative bacteria by C 60[>M(C 3N 6 +C 3) 2] and C 70[>M(C 3N 6 +C 3) 2], respectively. The hypothesis is that 1O 2 can diffuse more easily into porous cell walls of Gram-positive bacteria to reach sensitive sites, while the less permeable Gram-negative bacterial cell wall needs the more reactive HO {"}¢ to cause real damage.",

author = "Min Wang and Liyi Huang and Sharma, {Sulbha K.} and Seaho Jeon and Sammaiah Thota and Sperandio, {Felipe F.} and Suhasini Nayka and Julie Chang and Hamblin, {Michael R.} and Chiang, {Long Y.}",

year = "2012",

month = may,

day = "10",

doi = "10.1021/jm3000664",

language = "English",

volume = "55",

pages = "4274--4285",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

number = "9",

}

Wang, M, Huang, L, Sharma, SK, Jeon, S, Thota, S, Sperandio, FF, Nayka, S, Chang, J, Hamblin, MR & Chiang, LY 2012, 'Synthesis and photodynamic effect of new highly photostable decacationically armed [60]- and [70]fullerene decaiodide monoadducts to target pathogenic bacteria and cancer cells', Journal of Medicinal Chemistry, vol. 55, no. 9, pp. 4274-4285. https://doi.org/10.1021/jm3000664

Synthesis and photodynamic effect of new highly photostable decacationically armed [60]- and [70]fullerene decaiodide monoadducts to target pathogenic bacteria and cancer cells. / Wang, Min; Huang, Liyi; Sharma, Sulbha K. et al.
In: Journal of Medicinal Chemistry, Vol. 55, No. 9, 10.05.2012, p. 4274-4285.

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

TY - JOUR

T1 - Synthesis and photodynamic effect of new highly photostable decacationically armed [60]- and [70]fullerene decaiodide monoadducts to target pathogenic bacteria and cancer cells

AU - Wang, Min

AU - Huang, Liyi

AU - Sharma, Sulbha K.

AU - Jeon, Seaho

AU - Thota, Sammaiah

AU - Sperandio, Felipe F.

AU - Nayka, Suhasini

AU - Chang, Julie

AU - Hamblin, Michael R.

AU - Chiang, Long Y.

PY - 2012/5/10

Y1 - 2012/5/10

N2 - Novel water-soluble decacationically armed C 60 and C 70 decaiodide monoadducts, C 60- and C 70[> M(C 3N 6 +C 3) 2], were synthesized, characterized, and applied as photosensitizers and potential nano-PDT agents against pathogenic bacteria and cancer cells. A high number of cationic charges per fullerene cage and H-bonding moieties were designed for rapid binding to the anionic residues displayed on the outer parts of bacterial cell walls. In the presence of a high number of electron-donating iodide anions as parts of quaternary ammonium salts in the arm region, we found that C 70[>M(C 3N 6 +C 3) 2] produced more HO "¢ than C 60[> M(C 3N 6 +C 3) 2], in addition to 1O 2. This finding offers an explanation of the preferential killing of Gram-positive and Gram-negative bacteria by C 60[>M(C 3N 6 +C 3) 2] and C 70[>M(C 3N 6 +C 3) 2], respectively. The hypothesis is that 1O 2 can diffuse more easily into porous cell walls of Gram-positive bacteria to reach sensitive sites, while the less permeable Gram-negative bacterial cell wall needs the more reactive HO "¢ to cause real damage.

AB - Novel water-soluble decacationically armed C 60 and C 70 decaiodide monoadducts, C 60- and C 70[> M(C 3N 6 +C 3) 2], were synthesized, characterized, and applied as photosensitizers and potential nano-PDT agents against pathogenic bacteria and cancer cells. A high number of cationic charges per fullerene cage and H-bonding moieties were designed for rapid binding to the anionic residues displayed on the outer parts of bacterial cell walls. In the presence of a high number of electron-donating iodide anions as parts of quaternary ammonium salts in the arm region, we found that C 70[>M(C 3N 6 +C 3) 2] produced more HO "¢ than C 60[> M(C 3N 6 +C 3) 2], in addition to 1O 2. This finding offers an explanation of the preferential killing of Gram-positive and Gram-negative bacteria by C 60[>M(C 3N 6 +C 3) 2] and C 70[>M(C 3N 6 +C 3) 2], respectively. The hypothesis is that 1O 2 can diffuse more easily into porous cell walls of Gram-positive bacteria to reach sensitive sites, while the less permeable Gram-negative bacterial cell wall needs the more reactive HO "¢ to cause real damage.

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U2 - 10.1021/jm3000664

DO - 10.1021/jm3000664

M3 - Article

C2 - 22512669

AN - SCOPUS:84861026336

SN - 0022-2623

VL - 55

SP - 4274

EP - 4285

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 9

ER -

Synthesis and photodynamic effect of new highly photostable decacationically armed [60]- and [70]fullerene decaiodide monoadducts to target pathogenic bacteria and cancer cells

Abstract

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