Tetraphenylporphyrin-cobalt(III) Bis(1,2-dicarbollide) Conjugates: From the Solution Characteristics to Inhibition of HIV Protease

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• 作者：Pavel Kubá ; t ; Kamil Lang ; Petr C&iacute ; gler ; Milan Ko//pubs.acs.org/images/entities/zcaron.gif" border="0">&iacute ; //pubs.acs.org/images/entities/scaron.gif" borde
• 刊名：Journal of Physical Chemistry B
• 出版年：2007
• 出版时间：May 3, 2007
• 年：2007
• 卷：111
• 期：17
• 页码：4539 - 4546
• 全文大小：369K
• 年卷期：v.111,no.17(May 3, 2007)
• ISSN：1520-5207

文摘

Tetraphenylporphyrin conjugates with one (PB1) and four (PB4) cobalt(III) bis(1,2-dicarbollide) substituentswere synthesized and the physicochemical and photophysical properties as well as inhibition of HIV-1 proteasewere described. In methanol, both PB1 and PB4 were monomeric producing the triplet states and singletoxygen after excitation. The triplet states of PB4 were quickly protonated. Porphyrins exhibited a small decreaseof the quantum yields of the singlet oxygen formation (17% for PB4 and 13% for PB1) as compared with5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin. On the contrary, no singlet oxygen was detected in aqueoussolutions because of strong aggregation. Light scattering and atomic force microscopy (AFM) measurementsdocumented that the behavior of aggregates in aqueous solutions is fairly complex and depends on pH,concentration, and aging. The aggregation started from spherical particles in neutral solutions. In acidic solutions,extended aggregation occurred because of slow protonation of the porphyrin pyrrole nitrogen atoms. BothPB1 and PB4 are new representatives of nonpeptide HIV-1 protease inhibitors. Their activity increased withthe increasing number of the cobalt(III) bis(1,2-dicarbollide) substituents and was characterized with the IC₅₀values of 290 ± 44 nM for PB1 and 77 ± 13 nM for PB4.