22006-68-4Relevant academic research and scientific papers
A new cyclic thioanhydride derived from chlorophyll a and its aurophilic properties
Grin, Mikhail,Kirin, Nikita,Mironov, Andrey,Pogorilyy, Viktor
, (2021)
The need to modify the chlorine macrocycle by additional exocycles is dictated by the desire to increase the stability of the pigment, improve its spectral characteristics, including the shift of the main absorption band to the long-wavelength region, as well as the introduction of chemically active groups for the introduction of other bioactive molecules. Replacing the oxygen atom in the purpurin-18 anhydride exocycle with a sulfur atom can be considered as a bioisosteric substitution, which should not strongly affect the spectral and biological properties of the photosensitizer, but may allow the implementation of new chemical modifications at the periphery of the macrocycle. In this paper, we propose a synthesis pathway for a derivative of naturally occurring chlorin that contains an additional thioanhydride cycle attached to the main macrocycle. We report the spectral characteristics of the compound and demonstrate the possibility of immobilization of chlorin p6 thioanhydride on gold nanoparticles (Au-NP).
Conversion of purpurin 18 to chlorin P6 in the presence of silica, liposome and polymeric nanoparticles: A spectroscopic study
Jain, Beena,Uppal, Abha,Das, Kaustuv,Dube, Alok,Gupta, Pradeep Kumar
, p. 24 - 29 (2014)
Effect of nanoparticle (NP) environment on the conversion of entrapped photosensitizer purpurin 18 (Pp18) to chlorin p6 (Cp6) was studied spectroscopically. This was investigated by monitoring the time dependent absorption and emission kinetics of the Pp18 entrapped in four different NPs suspended in buffer at physiological pH in the presence and absence of serum up to 24 h. These were organically modified silica NP (SiNP) having vinyl and/or amino propyl groups, poly-lactic-co-glycolic acid (PLGA) NP and liposome. The results of the spectroscopic studies reveal that Pp18 is least converted to Cp6 (i.e., most stable) in the SiNP having vinyl groups whereas its conversion is fastest in PC liposome. In the presence of serum proteins, although the conversion is enhanced, the trend remains similar. Our investigation suggests that SiNP having vinyl functional groups might be a better carrier of Pp18 at physiological pH.
Design and synthesis of novel water-soluble amino acid derivatives of chlorin p6 ethers as photosensitizer
Zhang, Xingjie,Meng, Zhi,Ma, Zhiqiang,Liu, Junhong,Han, Guiyan,Ma, Fujia,Jia, Ningyang,Miao, Zhenyuan,Zhang, Wannian,Sheng, Chunquan,Yao, Jianzhong
, p. 247 - 249 (2018/05/23)
Eight new water-soluble amino acid conjugates 6a-h of chlorin p6 ethers (5a-d) were synthesized and preliminarily investigated for their in vitro PDT antitumor activity and structure-activity relationship (SAR). The results showed that all compounds exhibited much higher phototoxicity against tumor cells than talaporfin. SAR analysis indicated that PDT antitumor effect enhanced with the increase of carbon chain length of alkoxyl ether bonds at 31-position, and L-aspartic acid was superior to L-glutamic acid. In particular, the IC50 values of most phototoxic compound 6d were 0.20 μmol/L against A549 cell and 0.41 μmol/L against B16-F10 cell, which individually represented 31- and 24-fold increase of antitumor potency compared to talaporfin, suggesting that it was a promising candidate photosensitizer (PS) for PDT applications due to its strong absorption at long wavelength, high phototoxicity, low dark cytotoxicity and good water-solubility.
PHOTOSENSITISER AND METHOD FOR PRODUCTION THEREOF
-
Page/Page column 7; 14-15; 22-24, (2008/06/13)
The invention relates to medicine and concerns a photosensitiser for detecting and curing tumors. The inventive photosensitiser is embodied in the form of a composition containing chlorine in the form of salt and alkali metals. 80-90% of chlorine e6, 5-20% of purpurin 5 and the rest being purpurin 18 are used as chlorine. Said photosensitiser is produced by extracting Spirulina biomass with the aid of aceton. Afterwards said biomass is exposed to acid treatment, neutralisation, hydrolysis, extraction of feoforbide α, dissolution in aceton, addition of a strong base, neutralisation and reprecipitation of chlorine 6.
Synthesis of Model Ether-Linked Porphyrin-Chlorin Dimers
Levinson, E. G.,Mironov, A. F.
, p. 199 - 203 (2007/10/02)
Synthesis of model porphyrin-chlorin dimers with ether bond between the porphyrin rings was performed.The new heterodimers have intense absorption maxima in the range of 665-700 nm.Octaethylporphyrin was chosen as the hydrophobic moiety, and a chlorophyll derivative,purpurin 18, was used as the hydrophilic component.Opening of the anhydrine ring of purpurin 18 lead to chlorin p6 and its trimethyl ester.Dimeric derivatives with a different degree of chlorin carboxyls esterification were obtained to study regularities of the penetration of photosensitizer into tumors and its accumulation in them, in dependence on derivative amphiphilicity. Key words: photosensitizer, dimeric porphyrins, heterodimer, octaethylporphylin, purpurin 18, chlorin p6, amphiphilicity.
Synthesis and Study of Chlorin and Porphyrin Dimers with Ether Linkage
Brandis, Alexander S.,Kozyrev, Andrey N.,Mironov, Andrey F.
, p. 6485 - 6494 (2007/10/02)
Novel dimers of chlorophyll compounds (pheophorbide a, chlorin p6) and model porphyrin with ether linkage were synthesized and separated into components A and B (less and more polar).The ratio of these components was the same for all dimers and irrespective of reaction conditions.Method of dimerization through trifluoroacetoxyethylderivative gave higher yields. Key words: porphyrin dimer; chlorin dimer, pheophorbide; purpurin; stereoisomers
