- Acid response water-soluble near-infrared BODIPY light-sensitive agent and preparation method thereof
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The invention relates to an acid response water-soluble near-infrared BODIPY light-sensitive agent and a preparation method thereof. The novel BODIPY light-sensitive agent is soluble in water, has absorption performance in a near-infrared area, and has the advantages of being good in water solubility and high in light absorption in the near-infrared area. Meanwhile, the invention further provides the preparation method of the BODIPY light-sensitive agent. Synthesis is quick, and purification is easy. According to the preparation method, by reasonably designing feeding equivalence ratio, the target product can be obtained only through extraction, washing and other simple processing in triglycol monomethyl ether and p-toluenesulfonic acid sulfonylation; by means of the ethyl alcohol re-crystallization method, high-purity BODIPY is obtained; target molecules are synthesized at a high yield through reasonable temperature control. The method has the advantages of being easy to operate, convenient and safe to use and the like. The prepared light-sensitive agent can be soluble in water, the maximum absorption peak is 655 nm, the maximum emission peak is 710 nm, and the light emitting intensity of the light-sensitive agent is gradually improved along with addition of trifluoroacetic acid.
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Paragraph 0015
(2017/04/21)
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- Synthesis and structure-activity relationship studies of cytotoxic cinnamic alcohol derivatives
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Three series of di- and trisubstituted derivatives of cinnamic alcohol and its conjugated dienol analogues were designed and synthesised. The derivatives were screened for cytotoxicity against nine tumour cell lines: KB, A549, Hela, CNE, PC-3, BEL-7404, HL-60, BGC823 and P388D1. Most of the cinnamic alcohol derivatives showed cytotoxic activity. The compound 7-(4',5'-dichlorobenzyloxy)- 6,8-dihydroxycinnamic alcohol (55) exhibited significant cytotoxicity to seven human tumour cell lines on a micromolar range, especially with regard to the KB and P388D1 cell lines, showing IC50 values of 0.4 and 0.5μ M, respectively. The structure-activity relationships of the derivatives are discussed.
- Zou, Hong-Bin,Zhang, Liang,Yang, Lei-Xiang,Yang, Liu-Qing,Zhao, Yu,Yu, Yong-Ping,Stoeckigt, Joachim
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scheme or table
p. 203 - 221
(2011/04/15)
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- Bisdemethylcurcumin and structurally related hispolon analogues of curcumin exhibit enhanced prooxidant, anti-proliferative and anti-inflammatory activities in vitro
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Curcumin, a component of turmeric (Curcuma longa), exhibits anti-inflammatory and anti-proliferative activities through the generation of reactive oxygen species (ROS). Curcumin (diferuloylmethane) contains two hydroxyl, two methoxy and two phenyl groups but how these groups contribute to its activity is poorly understood. We synthesized analogues that varied in inclusion of these groups and compared their activity. We found that bisdemethylcurcumin (BDC) was more potent than curcumin as an anti-inflammatory agent as indicated by suppression of TNF-induced NF-κB activation, more potent as an anti-proliferative agent, and more potent in inducing ROS. Hispolon, which lacks one aromatic unit in relation to curcumin, also exhibited enhanced anti-inflammatory and anti-proliferative activities. When synthetic curcumin (Cur-S) was compared with bisdemethylcurcumin (BDC), hispolon, hispolon methyl ether (HME), dehydroxy hispolon (DH), hydroxy hispolon (HH), methoxy hispolon methyl ether (MHME), and methoxy hispolon (MH), we found that following order of anti-inflammatory activity: BDC=Hispolon>HME>HH>Cur-S>MHME>MH>DH; for anti-proliferative: Hispolon>BDC>MHME>Cur-S>MH>HME=HH>DH; and for prooxidant: BDC>Cur-S=MHME>HH>MH+HME>DH (254-1414 mean fluorescence intensity). Thus, dehydroxy hispolon was least potent for all three activities. Overall the results indicate that the substitution of a hydroxyl group for a methoxy group at the meta positions of the phenyl rings in curcumin significantly enhanced the anti-inflammatory activity, and the removal of phenyl ring at the 7th position of the heptadiene back bone and addition of hydroxyl group significantly increased the anti-proliferative activity of curcumin.
- Ravindran, Jayaraj,Subbaraju, Gottumukkala V.,Ramani, Modukuri V.,Sung, Bokyung,Aggarwal, Bharat B.
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experimental part
p. 1658 - 1666
(2011/11/29)
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- Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives
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Five series totalling 51 of sinapyl alcohol derivatives were designed and synthesized. Their cytotoxicity analyses were performed on six human tumor cell lines such as PC-3, CNE, KB, A549, BEL-7404, and HeLa. Certain sinapyl alcohol derivatives showed significant cytotoxic activities. Compound 14d exhibited especially potent cytotoxicity against the BEL-7404 cell line with an IC 50 value of 0.7 μM, which showed more cytotoxic activity than the positive control, cisplatin. The structure-cytotoxicity relationships were discussed and the CoMFA analysis was performed using the cytotoxic data against HeLa cells as a template.
- Zou, Hong Bin,Dong, Sheng Yi,Zhou, Chang Xin,Hu, Li Hong,Wu, Yi Hang,Li, Hai Bo,Gong, Jing Xu,Sun, Lian Li,Wu, Xiu Mei,Bai, Hua,Fan, Bo Tao,Hao, Xiao Jiang,Stoeckigt, Joachim,Zhao, Yu
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p. 2060 - 2071
(2007/10/03)
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