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

62 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

UN SDGs

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

SDG 3 Good Health and Well-being

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

Access to Document

10.1021/jm3000664

Cite this

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.

UR - https://www.scopus.com/pages/publications/84861026336

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

UN SDGs

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this