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Ruthenium (II) porphyrin complex connected by flexible carbon chain and preparation method and application thereof

A technology of porphyrin complexes and complexes, applied in the field of ruthenium porphyrin complexes and their preparation, can solve the problems of strong toxicity and low activity

Inactive Publication Date: 2013-01-09
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The object of the present invention is to provide a kind of ruthenium (II) porphyrin complex connected with flexible carbon chain according to the problems of strong toxicity and low activity in existing anticancer drugs

Method used

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  • Ruthenium (II) porphyrin complex connected by flexible carbon chain and preparation method and application thereof
  • Ruthenium (II) porphyrin complex connected by flexible carbon chain and preparation method and application thereof
  • Ruthenium (II) porphyrin complex connected by flexible carbon chain and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1Ru(bpy) 2 Synthesis of (4-p)POTPP

[0042] cis-[Ru(bpy) 2 Cl 2 ].H 2 Synthesis of O: RuCl 3 .nH 2 O, bipyridyl and lithium chloride in a three-necked flask, add 15ml of DMF, and reflux for 8h under the protection of argon. Cool to room temperature, add 50ml of acetone, freeze overnight. Suction filtration, the precipitate was washed several times with ice water and cold acetone, and dried in vacuum to obtain black microcrystals.

[0043] Synthesis of o-phenanthroline 5,6-dione: 1,10-phenanthroline, potassium bromide in a three-necked flask, slowly drop concentrated H under ice bath 2 SO 4 / concentrated HNO 3 Mix the acid in a three-necked flask. After the dropwise addition, react in an oil bath for 3 hours. After the reaction, ice water was added, the pH of the system was adjusted to close to 7 with NaOH, extracted with chloroform, and the chloroform was spin-dried to obtain yellow o-phenanthroline-5,6-dione.

[0044] Synthesis of 4-hydroxy-imidazo[...

Embodiment 2

[0050] Example 2Ru(phen) 2 Synthesis of (4-p)POTPP

[0051] cis-[Ru(phen) 2 Cl 2 ].H 2 Synthesis of O: See Example 1. Just replace the bipyridine in method 1 with o-phenanthroline to participate in the reaction.

[0052] 4-Hydroxy-imidazo[4,5-f][1,10]o-phenanthroline-diphenanthroline ruthenium Ru(phen) 2 Synthesis of p-Hpip: See Example 1.

[0053] Synthesis of 5-[4-(3-bromopentyloxy)phenyl]-10,15,20-triphenylporphyrin (p-POBrTPP): See Example 1.

[0054] 5-{4-{4'-Hydroxyimidazolium[1,10]o-phenanthroline-diphenanthroline ruthenium-pentyloxy}phenyl}-10,15,20-triphenylporphyrin [Ru( phen) 2 Synthesis of (4-p)POTPP]:

[0055] p-POBrTPP, Ru(phen) 2 p-Hpip was heated to reflux in DMF, and after cooling to room temperature, the solution was poured into saturated saline, left to stand for a while, suction filtered, washed with water several times, and vacuum-dried to obtain a purple crude product, which was purified by column chromatography and rinsed with chloroform. Coll...

Embodiment 3

[0057] Embodiment 3Ru(4,4'-Me)(bpy) 2 Synthesis of (4-p)POTPP

[0058] cis-[Ru(4,4'-Me)(bpy) 2 Cl 2 ].H 2 Synthesis of O: See Example 1. Just replace the bipyridine in method 1 with 4,4'-dimethylbipyridine to participate in the reaction.

[0059] 4-Hydroxy-imidazo[4,5-f][1,10]phenanthroline-(4,4'-dimethyl)bipyridine Ru(4,4'-Me)(bpy) 2 Synthesis of p-Hpip: See Example 1.

[0060] Synthesis of 5-[4-(3-bromopentyloxy)phenyl]-10,15,20-triphenylporphyrin (p-POBrTPP): See Example 1.

[0061]5-{4-{4'-Hydroxyimidazolium[1,10]phenanthroline-(4,4'-dimethyl)bipyridine ruthenopentyloxy}phenyl}-10,15,20 -Triphenylporphyrin [Ru(4,4'-Me)(bpy) 2 Synthesis of (4-p)POTPP]:

[0062] p-POBrTPP, Ru(4,4'-Me)(bpy) 2 p-Hpip was heated to reflux in DMF, and after cooling to room temperature, the solution was poured into saturated saline, left to stand for a while, suction filtered, washed with water several times, and vacuum-dried to obtain a purple crude product, which was purified by colum...

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Abstract

The invention discloses a ruthenium (II) porphyrin by a flexible carbon chain and a preparation method and application thereof. A structural formula of the ruthenium (II) porphyrin complex is expressed as a formula (I), wherein R1 may be H, OCH3, NO2, COOH, CF3, OH, NH2, halogen, CH3, 3'-OCH3, 4'-OH, 3'-OH, 4'-OCH3, CH2H5, C3H7, C4H9, OC2H5, NOCH3, COOCH3 or CONH2; n is a natural number; X may beRu(bpy)2, Ru(dmbpy)2, Ru(phen)2, Ru(phendione)2, Ru(ip)2, Ru(arene)2 or is not any group; Ru is ruthenium metal; bpy is 2,2'-bipyridyl; dmbpy is 4,4'-dimethyl-2,2'-bipyridyl; phen is phenanthroline, phendione is phenanthroline 5,6-diketone, ip is 2-phenylimidazole[4,5-f] [1,10] phenanthroline, and arene is benzene ring; and M may be H2, Cu, Co, Ni, Mn or Zn. The complex is a series ruthenium porphyrin complex starting from the molecular level by connecting porphyrin and ruthenium through an ether bond and using DNA as an in vitro target point, and can be used for preparing anti-cancer medicaments with low toxic or side effect and high activity.

Description

technical field [0001] The invention relates to the field of preparation of ruthenium complexes, in particular to a ruthenium (II) porphyrin complex linked by a flexible carbon chain, a preparation method and application thereof. Background technique [0002] Porphyrin and its derivatives widely exist in organisms and in important organelles related to energy transfer. The vast majority of porphyrin compounds in nature exist in the form of metal porphyrins, mainly in heme (iron porphyrin) and hemocyanin (copper porphyrin) in animals, and mainly in vitamin B in plants 12 (cobalt porphyrin) and chlorophyll (magnesium porphyrin), are the key substances in animal blood cells carrying oxygen for respiration and plant cells for light and action. Therefore, people have paid more attention to the research of porphyrins, and many porphyrin compounds have been widely used in the field of medicine. At present, porphyrin compounds are mainly used as anticancer drugs clinically. [00...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00A61K31/555A61K41/00A61P35/00
Inventor 梅文杰蒋小磊
Owner GUANGDONG PHARMA UNIV