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WO2006001430A1 - COMPOSE DE PORPHYRINE PRESENTANT UNE STRUCTURE DE SUBSTITUTION α3β , COMPLEXE METALLIQUE DE CE COMPOSE ET INFUSION D'OXYGENE CONTENANT CE COMPOSE - Google Patents

COMPOSE DE PORPHYRINE PRESENTANT UNE STRUCTURE DE SUBSTITUTION α3β , COMPLEXE METALLIQUE DE CE COMPOSE ET INFUSION D'OXYGENE CONTENANT CE COMPOSE Download PDF

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Publication number
WO2006001430A1
WO2006001430A1 PCT/JP2005/011760 JP2005011760W WO2006001430A1 WO 2006001430 A1 WO2006001430 A1 WO 2006001430A1 JP 2005011760 W JP2005011760 W JP 2005011760W WO 2006001430 A1 WO2006001430 A1 WO 2006001430A1
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group
metal complex
porphyrin
formula
albumin
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Japanese (ja)
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Eishun Tsuchida
Teruyuki Komatsu
Akito Nakagawa
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06—Antianaemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock

Definitions

  • the present invention relates to a borfilin compound or a metal complex thereof that can be used as an artificial oxygen carrier, and an inclusion compound containing the compound.
  • the FeTpivPP complex can be used in an organic solvent such as benzene, toluene, dichloromethane, tetrahydrofuran, N, N dimethylformamide at room temperature in the presence of an excess axial base such as 1 alkyl imidazole, 1 alkyl 2-methylimidazole, etc.
  • Oxygen molecules can be adsorbed and desorbed reversibly, and if this complex is embedded in a bilayer vesicle composed of phospholipids, the same applies even under physiological conditions (aqueous phase, pH 7.4, 37 ° C). Exerts its oxygen bond dissociation ability That (e.g., E.
  • the present inventors can supply a stable oxygen carrier without external addition of an axial base by covalently bonding an imidazole derivative as a side chain substituent into the porphyrin iron (II) complex molecule.
  • an imidazole derivative as a side chain substituent into the porphyrin iron (II) complex molecule.
  • a FeTpivPP analog having a substituent at the 2-position of the porphyrin ring, and prepared a clathrate compound containing this in human serum albumin in the phospholipid endoplasmic reticulum.
  • It is provided as an artificial oxygen carrier that can be adsorbed and desorbed (Japanese Patent Laid-Open No. 59-164791, Japanese Patent Laid-Open No. 59-162924, Japanese Patent Laid-Open No.
  • an imidazolylalkyl group as an axial base ligand was bonded to one of the amino groups of tetrakis-o-aminoporphyrin, and a hydrophobic substituent was bonded to the other three amino groups.
  • porphyrin metal complexes include JP Collman et al., J. Am. Chem. Soc, 10 02, 4182 (1980) and 5- (imidazolylalkylenamide phenol) 1, 10, 15, 20 tris (pivalamide phenol- Le) Borhu Irinato iron is described.
  • these vorphiline derivatives are obtained by first attaching three bivaloyl groups to tetrakis o-, a, a, ⁇ -aminophenol-porphyrin and then atropisomerizing the remaining one amino group. (Ie a ⁇ structure) and imidazolyl groups are synthesized in order, and the total yield is as low as 5% or less.
  • the hydrophobic substituent of this porphyrin metal complex is a bivaloyl group, it is not possible to sufficiently cover the vicinity of the oxygen coordination locus with only three, so that even if a small amount of water coexists, it is immediately oxidized and the oxygen complex is formed. Cannot be formed.
  • the present invention eliminates the above-mentioned problems of the prior art and efficiently produces a stable oxygen complex that effectively acts as an oxygen infusion solution with a smaller number of steps. Therefore, the tetrakis-amino-phenol is used.
  • the object is to provide a novel ⁇ 3 18-substituted porphyrin metal complex in which an axial base ligand is introduced into one amino group of porphyrin and a hydrophobic substituent is introduced into the remaining three amino groups.
  • R is an alicyclic hydrocarbon group which may have a substituent, and R is a group represented by the formula [II]: [Chemical 2] Formula [
  • R is an alkylene group, R is a coordinated transition metal ion M of the 4th to 5th periods of the periodic table
  • 5 6 is an axial base coordinating group represented by 0 or 1), or a porphyrin compound represented by
  • the metal complex coordinated with five periods of transition metal ions is provided.
  • porphyrin metal complex-albumin inclusion complex obtained by including the porphyrin metal complex of the present invention in albumin.
  • an artificial oxygen carrier comprising the porphyrin metal complex-albumin inclusion compound of the present invention as an active ingredient.
  • R represents an alicyclic hydrocarbon group which may have a substituent.
  • the preferred hydrocarbon group is preferably an alicyclic hydrocarbon group having a substituent at the 1-position, which can effectively bring the central part of the relatively bulky Borfilin compound into the hydrophobic atmosphere.
  • Examples of such an alicyclic hydrocarbon group having a substituent at the 1-position include 1-substituted cyclopropyl group, 1-substituted cyclopentyl group, 1-substituted cyclohexyl group, 1-methyl 2-cyclohexyl. Group, 2-substituted norbornyl group, 1-adamantyl group, 1
  • the position substituent include a methyl group, an alkylamide group (RCONH), an alkyl ester group (ROOC), and an alkyl ether group (RO).
  • the alkyl group represented by R is preferably a C to C alkyl group.
  • R is an axial base coordinating group represented by the above formula [II] or the above formula [III].
  • R is an alkylene group, preferably a C to C alkylene group.
  • R represents glycine, alanine, valine, leucine, isoleucine, serine,
  • the carboxyl group of amino acids such as leonine and phenylalanine
  • R is a hydrophobic group such as hydrogen, acetyl group, benzyl
  • the present invention also provides a porphyrin metal complex in which a transition metal ion M in the 4th to 5th periods of the periodic table is coordinated to the borfilin compound of the formula [I].
  • the transition metal ion M is preferably Fe or Co.
  • the valence of Fe can be +2 or +3, and the valence of Co can be +2.
  • This porphyrin metal complex can be represented by the formula [IV].
  • X— represents a halide ion such as a chloride ion or a bromide ion.
  • the number n of X— is the number obtained by subtracting 2 from the valence of the transition metal ion M.
  • the imidazole group bonded in the molecule coordinates to the porphyrin central metal M as a proximal base.
  • This state can be expressed by the following formula [V].
  • the imidazole group coordinated to the central metal M corresponds to the imidazole group in Formula [II] or Formula [III].
  • the R group in Formula [II] is excluded. It is. In addition, it was bonded to the ortho position of phenyl.
  • the wavy line connecting nitrogen and the imidazole group represents the residue in the formula [II] or [III] except the imidazole ring.
  • this imidazole group When this imidazole group is coordinated to the central metal M, the oxygen-binding ability can be exhibited only by the Borfilin complex molecule. Thereby, it is not necessary to add an imidazole derivative excessively as an axial base ligand. Furthermore, an imidazole group can be bonded into the molecule without introducing a substituent at the 2-position of the porphyrin.
  • This metal complex can form a stable oxygen complex in water when included in albumin such as ushi serum albumin, human serum albumin, recombinant human serum albumin, albumin multimer, etc.
  • albumin such as ushi serum albumin, human serum albumin, recombinant human serum albumin, albumin multimer, etc.
  • the function of Inclusion of the metal complex into albumin can be performed using, for example, the technique described in JP-A-2003-040893.
  • the porphyrin metal complex of the present invention includes an artificial oxygen carrier, a gas adsorbent, an acid It will also have features as a catalytic reduction catalyst, oxygen oxidation reaction catalyst, and oxygen addition reaction catalyst.
  • Artificial oxygen carriers can be used as a substitute for blood for transfusion, preoperative blood diluent, supplemental fluid for extracorporeal circuit such as artificial heart and lung, perfusion fluid for transplanted organ, oxygen to ischemic site Supply fluid, chronic anemia treatment agent, liquid ventilation perfusate, sensitizer for cancer treatment, culture solution of regenerative tissue cells, use for rare blood group patients, response to transfusion refusal patients for religious reasons, Application to animal medicine is expected.
  • the artificial oxygen carrier is obtained by dispersing the porphyrin metal complex albumin inclusion complex of the present invention in physiological saline.
  • concentration of the porphyrin metal complex albumin inclusion complex varies depending on the application, but a blood substitute of about 9.2 mmol ZL can be used as a blood substitute, and other concentrations can be used.
  • the method for producing the borfilin compound of the present invention is not particularly limited.
  • a mesotetrakis (a, a, a, ⁇ -o aminophenol) porphyrin represented by the following formula [VI] is used. It can be synthesized as a starting material.
  • meso-tetrakis (a, a, a, ⁇ -o aminophenol) porphyrin is dissolved in an appropriate organic solvent (for example, black form, tetrahydrofuran, etc.), and trityl bromide is dissolved therein.
  • an appropriate organic solvent for example, black form, tetrahydrofuran, etc.
  • trityl bromide is dissolved therein.
  • Triethylamine and stir for another 10 minutes to 1 hour, and then remove the solvent under reduced pressure.
  • Alumina is filtered off with a glass filter, and mesotri (a, a, ⁇ -o aminophenyl) porphyrin is fractionated and purified by a silica gel column (o- (N triphenylmethyl) aminophenyl) porphyrin. Obtained po A solution of rufilin and a suitable base (pyridine, 4-dimethylaminopyridine, triethylamine, etc.) in a suitable organic solvent (eg, chloroform, tetrahydrofuran, etc.)
  • a nitrogen atmosphere is added dropwise to the acid chloride represented by COC1 (where R is as defined above).
  • porphyrin metal complexes when they are in the form of iron (in) complexes, an appropriate reducing agent (sodium nithionite, ascorbic acid, etc.) is used, and the central metal is trivalent to divalent by a conventional method. If reduced to oxygen, oxygen binding activity can be imparted.
  • These porphyrin iron (II) complexes are systematically encapsulated in human serum albumin, system encapsulated in recombinant human serum albumin, system encapsulated in albumin polymer, and in any case, stable immediately when contacted with oxygen A simple oxygen complex. Further, these complexes can adsorb and desorb oxygen according to the oxygen partial pressure. This oxygen bond dissociation can be repeated reversibly and acts as an oxygen adsorption / desorption agent and oxygen carrier.
  • the porphyrin metal complex of the present invention is a free imidazole with high body toxicity that can be applied as a redox reaction catalyst and gas adsorbent in homogeneous and heterogeneous systems.
  • the iron (II) or cobalt (II) complex has characteristics as an artificial oxygen carrier because it can be easily synthesized by eliminating its existence.
  • 6-Bromohexanoic acid (1. Og, 5.35 mmol) and oxalyl chloride (0.7 mL) were added to a 50 mL three-necked flask, and the mixture was stirred at room temperature for 3 hours, and oxalyl chloride was removed under reduced pressure. Thereto was added dropwise a solution of biphenyl-carbinol (1.29 g, 7.02 mmol) and triethylamine (1 mL) in black mouth form (5 mL), and the mixture was stirred at 60 ° C. for 2 hours under a nitrogen atmosphere.
  • 6-bromohexanoic acid diphenylmethyl ester was obtained in a yield of 1.57 g (yield 80%).
  • Example 2 To the other 50 mL of triflasco, the mesotriol obtained in Example 2 (a, a, ⁇ — o— (1-methylcycloquinamide)) j8— o— (N triphenyl-methyl) aminophenol porphyrin ( 200 mg, 0.155 mmol) and 30 mL of chloroform were added and stirred for 15 minutes while blowing hydrogen chloride gas. At this time, the color of the solution changed from magenta to green. Pure water and sodium hydrogen carbonate were added to adjust the pH to 7, followed by extraction with black mouth form, washing with water, dehydration with anhydrous sodium sulfate, and removal of the solvent under reduced pressure to obtain a purple solid.
  • Example 6 the mesotriol obtained in Example 6 (a, a, a— o— 1 methylcyclohexaneamide phenol) (j8 —0— 6— (N— (2-methyl-1-imidazolyl)) hexaneamide 4 mL of a tetrahydrofuran solution of (phenol) porphyrin (34 mg ⁇ 0.03 mmol) and 2,6-lutidine (48 L, 0.41 mmol) was added dropwise, and the mixture was stirred at 60 ° C. for 2 hours under a nitrogen atmosphere. After confirming the disappearance of fluorescence (ex. 420 nm, em.
  • Example 1 1-methylcyclopentanoic acid was used instead of 1-methylcyclohexanoic acid, and in Example 6, 6- (2-methyl-1imidazolyl) hexanoic acid was used instead of 4
  • Example 6 2-methyl-1imidazolyl hexanoic acid was used instead of 4
  • 1 (1 imidazolyl) butanoic acid is used, and follow meso-tri (a, a, ⁇ - o- (1-methyl) cyclopentanamide phenol) 1 j8— o— 4— (N-1—imidazolyl) butanamide phenol-porphyrin iron was synthesized.
  • Example 1 1-adamantanic acid was used instead of 1-methylcyclohexanoic acid, and in Example 6, 10- (2-methyl-1 imidazolyl) decanoic acid was used instead of 6- (2-methyl-1 imidazolyl) hexanoic acid.
  • mesotriol a,, ⁇ — o adamantanamide phenol-nor
  • j8— o— 10— N— (2-methyl 1 —Imidazolyl)
  • Example 1! /, 1 Method using 3-noradamantanecarboxylic acid instead of methylcyclohexanoic acid, and further reacting with cobalt chloride in dry tetrahydrofuran containing 2,6-lutidine in Example 7 In Example 1 except that cobalt is introduced into the porphyrin center.
  • step 7 sort the messortry ( ⁇ , ⁇ , ⁇ — ⁇ — 3—noradamantanamide E) ⁇ -0-6- ( ⁇ - (2-Methyl-1 imidazolyl)) hexamide phenylporphyrin cobalt was synthesized.
  • mesotriol (a, a, a-o-l-methylcyclohex A toluene solution of sanamide phenol)-(j8—o—6— (N— (2-methyl-1-imidazolyl)) hexanamide phenol) porphyrin iron ( ⁇ ) complex was obtained.
  • the visible absorption spectrum of this solution is ⁇ : 427, 532, 559 nm, and the complex is 5-coordinated with one imidazole coordinated max
  • oxygenated complex was revealed.
  • nitrogen gas was blown into this oxygenated complex solution for 1 minute, the visible absorption spectrum reversibly changed from the oxygenated spectrum to the deoxy type spectrum, so that it is clear that oxygen adsorption / desorption occurs reversibly. Helped.
  • oxygen adsorption / desorption could be continuously performed.
  • Oxygenated complex formation was shown. When nitrogen gas is blown into this oxygenated complex solution for 1 minute, the visible absorption spectrum reversibly changes to the oxygenated spectral force deoxy type spectrum, and it is clear that the adsorption / desorption of oxygen occurs reversibly. It was. In addition, it was possible to continuously perform oxygen adsorption / desorption by repeating the operation of blowing oxygen and then nitrogen. The oxygen affinity P was 45 Torr. In addition, this oxygen coordination complex gradually deteriorates
  • the half-life was about 4 hours (37 ° C).
  • the porphyrin metal complex of the present invention is one in which an axial base group ligand is simply introduced into the porphyrin metal complex to provide an excellent oxygen transport capability.
  • the total yield was about 20%, and the target product could be obtained more efficiently than the conventionally reported axial base-bonded porphyrin metal complex with ⁇ 3 18 structure.
  • the porphyrin metal complex is The porphyrin metal complex-albumin inclusion complex encapsulated in serum albumin can be a useful material excellent in biocompatibility when considered for in vivo administration as an artificial oxygen carrier.
  • the porphyrin metal complex of the present invention is useful as a gas adsorbent, an oxygen adsorbing / desorbing agent, a redox catalyst, an oxygen oxidation reaction catalyst, and the like.

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Abstract

La présente invention concerne un composé de porphyrine représenté par la formule [I] ou un complexe métallique de ce composé. Dans la formule [I], R1 représente un groupe hydrocarbure alicyclique éventuellement substitué et R2 représente un groupe de coordination de base axial représenté par la formule [II] ou un groupe similaire.
PCT/JP2005/011760 2004-06-28 2005-06-27 COMPOSE DE PORPHYRINE PRESENTANT UNE STRUCTURE DE SUBSTITUTION α3β , COMPLEXE METALLIQUE DE CE COMPOSE ET INFUSION D'OXYGENE CONTENANT CE COMPOSE Ceased WO2006001430A1 (fr)

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JP2004190189A JP2006008622A (ja) 2004-06-28 2004-06-28 α３β置換構造のポルフィリン化合物もしくはその金属錯体、およびそれを含有する酸素輸液
JP2004-190189 2004-06-28

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1880721A4 (fr) * 2005-05-12 2009-05-27 Nipro Corp Agent ameliorant les troubles circulatoires

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CN111504994B (zh) * 2020-05-07 2022-02-18 山东省地质矿产勘查开发局第一地质大队 基于卟啉的多孔有机聚合物及其在硫离子比色检测中的应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08301873A (ja) * 1995-04-28 1996-11-19 Hidetoshi Tsuchida ポルフィリン金属錯体−アルブミン包接化合物及び酸素運搬体
JP2002128781A (ja) * 2000-10-19 2002-05-09 Japan Science & Technology Corp 塩基性軸配位子を有する置換テトラフェニルポルフィリン化合物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08301873A (ja) * 1995-04-28 1996-11-19 Hidetoshi Tsuchida ポルフィリン金属錯体−アルブミン包接化合物及び酸素運搬体
JP2002128781A (ja) * 2000-10-19 2002-05-09 Japan Science & Technology Corp 塩基性軸配位子を有する置換テトラフェニルポルフィリン化合物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
COLLMAN J. ET AL.: "Synthesis and Characterization of "Tailed Picket Fence" Porphyrins.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 102, no. 12, 4 June 1980 (1980-06-04), pages 4182 - 4192, XP002991508 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1880721A4 (fr) * 2005-05-12 2009-05-27 Nipro Corp Agent ameliorant les troubles circulatoires

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