スペルミン
概要
説明
スペルミンは、細胞代謝に関与し、すべての真核細胞に存在する天然のポリアミンです。 それはアミノ酸オルニチンから誘導され、特にウイルスにおける核酸のらせん構造の安定化に重要な役割を果たしています 。 スペルミンは、細胞内フリーラジカルスカベンジャーとしての役割も知られており、DNAを酸化損傷から保護しています .
2. 製法
合成経路および反応条件: スペルミンは、スペルミジンシンターゼ酵素の作用により、スペルミジンから合成されます。 このプロセスには、スペルミジンへのアミノプロピル基の転移が含まれます 。 反応条件は通常、補因子として脱炭酸S-アデノシルメチオニンの存在を必要とします .
工業生産方法: スペルミンの工業生産は、オルニチンの脱炭酸によるプトレッシンの生成から始まり、次にスペルミジンに変換されます。 最後に、スペルミジンはN-アルキル化反応によってスペルミンに変換されます 。 このプロセスは、温度、pH、反応物の濃度などの反応条件を制御することで、大規模生産向けに最適化されています .
科学的研究の応用
スペルミンは、科学研究で幅広い用途があります。
作用機序
スペルミンは、いくつかのメカニズムを通じてその効果を発揮します。
フリーラジカルスカベンジング: スペルミンは、フリーラジカルスカベンジャーとして働き、DNAを酸化損傷から保護します.
遺伝子調節: 遺伝子発現の調節とクロマチン安定化に関与しています.
分子標的との相互作用: スペルミンはDNAに結合し、エンドヌクレアーゼによるDNA断片化を防ぎ、らせん構造を安定化します.
6. 類似の化合物との比較
スペルミンは、スペルミジン、プトレッシン、カダベリンを含むポリアミンのファミリーの一部です .
スペルミジン: スペルミンに似ていますが、アミノプロピル基が1つ少ないです。
生化学分析
Biochemical Properties
Spermine interacts with various enzymes, proteins, and other biomolecules. The precursor for the synthesis of spermine is the amino acid ornithine . Spermine biosynthesis in animals starts with the decarboxylation of ornithine by the enzyme Ornithine decarboxylase in the presence of PLP . This decarboxylation gives putrescine, which is then converted to spermine .
Cellular Effects
Spermine has been shown to protect cells from a variety of environmental insults . It is associated with nucleic acids and is thought to stabilize helical structure, particularly in viruses . It functions as an intracellular free radical scavenger to protect DNA from free radical attack . Spermine also plays a role in enhancing antioxidant defense mechanisms, glyoxalase systems, methylglyoxal (MG) detoxification, and creating tolerance for drought-induced oxidative stress in plants .
Molecular Mechanism
Spermine exerts its effects at the molecular level through various mechanisms. It functions directly as a free radical scavenger, forming a variety of adducts that prevent oxidative damage to DNA . It also interferes with the binding and stabilization of certain DNA intercalators to DNA .
Temporal Effects in Laboratory Settings
Over time, spermine’s effects can change in laboratory settings. For instance, drought stress increases endogenous spermine in plants, and exogenous application of spermine improves the plants’ ability to tolerate drought stress .
Dosage Effects in Animal Models
The effects of spermine can vary with different dosages in animal models. For example, supplementation of cells with exogenous spermine decreases matrix mineralization in a dose-dependent manner .
Metabolic Pathways
Spermine is involved in several metabolic pathways. In one pathway, L-glutamine is the precursor to L-ornithine, after which the synthesis of spermine from L-ornithine follows the same pathway as in animals . Another pathway in plants starts with decarboxylation of L-arginine to produce agmatine .
Transport and Distribution
Spermine is transported into the mitochondrial matrix by an electrophoretic mechanism having the negative electrical membrane potential (ΔΨ) as the driving force . The presence of phosphate increases spermine uptake by reducing ΔpH and enhancing ΔΨ .
Subcellular Localization
Spermine is primarily found in the nucleus . Subcellular localization studies indicate that spermine is a cytosolic protein undergoing proteasomal control .
準備方法
Synthetic Routes and Reaction Conditions: Spermine is synthesized from spermidine through the action of the enzyme spermine synthase. The process involves the transfer of an aminopropyl group to spermidine . The reaction conditions typically require the presence of decarboxylated S-adenosyl methionine as a cofactor .
Industrial Production Methods: Industrial production of spermine involves the decarboxylation of ornithine to produce putrescine, which is then converted to spermidine. Finally, spermidine is transformed into spermine through N-alkylation reactions . The process is optimized for large-scale production by controlling reaction conditions such as temperature, pH, and the concentration of reactants .
化学反応の分析
反応の種類: スペルミンは、酸化、還元、置換など、さまざまな化学反応を起こします .
一般的な試薬と条件:
酸化: スペルミンは、スペルミンオキシダーゼなどの酵素によって酸化され、過酸化水素とアミノアルデヒドを生成します.
還元: スペルミンを伴う還元反応はあまり一般的ではありませんが、特定の条件下で還元剤の存在下で起こりえます。
主要な生成物: これらの反応から生成される主要な生成物には、過酸化水素、アミノアルデヒド、およびさまざまな置換スペルミン誘導体があります .
類似化合物との比較
Spermine is part of a family of polyamines that includes spermidine, putrescine, and cadaverine .
Spermidine: Similar to spermine but with one less aminopropyl group.
Putrescine: A precursor to both spermidine and spermine, it plays a role in cell growth and differentiation.
Cadaverine: Structurally similar but with different biological functions, primarily involved in bacterial metabolism.
Spermine is unique due to its higher number of amino groups, which enhances its ability to stabilize nucleic acids and protect against oxidative damage .
特性
IUPAC Name |
N,N'-bis(3-aminopropyl)butane-1,4-diamine |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
PFNFFQXMRSDOHW-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C(CCNCCCN)CNCCCN |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C10H26N4 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Related CAS |
71052-31-8 |
Source
|
| Record name | 1,4-Butanediamine, N1,N4-bis(3-aminopropyl)-, homopolymer | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=71052-31-8 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
DSSTOX Substance ID |
DTXSID9058781 |
Source
|
| Record name | N1,N4-Bis(3-aminopropyl)-1,4-butanediamine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID9058781 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
202.34 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid; Absorbs carbon dioxide from air; [Merck Index] Colorless solidified mass or fragments; mp = 28-30 deg C; [Sigma-Aldrich MSDS], Solid |
Source
|
| Record name | Spermine | |
| Source | Haz-Map, Information on Hazardous Chemicals and Occupational Diseases | |
| URL | https://haz-map.com/Agents/21744 | |
| Description | Haz-Map® is an occupational health database designed for health and safety professionals and for consumers seeking information about the adverse effects of workplace exposures to chemical and biological agents. | |
| Explanation | Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission. | |
| Record name | Spermine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001256 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Boiling Point |
150-150 °C |
Source
|
| Record name | Spermine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00127 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
Solubility |
> 100 mg/mL |
Source
|
| Record name | Spermine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00127 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
Mechanism of Action |
Spermine is derived from spermidine by spermine synthase. Spermine is a polyamine, a small organic cations that is absolutely required for eukaryotic cell growth. Spermine, is normally found in millimolar concentrations in the nucleus. Spermine functions directly as a free radical scavenger, and forms a variety of adducts that prevent oxidative damage to DNA. Oxidative damage to DNA by reactive oxygen species is a continual problem that cells must guard against to survive. Hence, spermine is a major natural intracellular compound capable of protecting DNA from free radical attack. Spermine is also implicated in the regulation of gene expression, the stabilization of chromatin, and the prevention of endonuclease-mediated DNA fragmentation. |
Source
|
| Record name | Spermine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00127 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
CAS No. |
71-44-3, 68956-56-9 |
Source
|
| Record name | Spermine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=71-44-3 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Spermine | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000071443 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Hydrocarbons, terpene processing by-products | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0068956569 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Spermine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00127 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | spermine | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=268508 | |
| Description | The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. | |
| Explanation | Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. | |
| Record name | 1,4-Butanediamine, N1,N4-bis(3-aminopropyl)- | |
| Source | EPA Chemicals under the TSCA | |
| URL | https://www.epa.gov/chemicals-under-tsca | |
| Description | EPA Chemicals under the Toxic Substances Control Act (TSCA) collection contains information on chemicals and their regulations under TSCA, including non-confidential content from the TSCA Chemical Substance Inventory and Chemical Data Reporting. | |
| Record name | N1,N4-Bis(3-aminopropyl)-1,4-butanediamine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID9058781 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | 4,9-diazadodecamethylenediamine | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.000.686 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | SPERMINE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/2FZ7Y3VOQX | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
| Record name | Spermine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001256 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
29 °C |
Source
|
| Record name | Spermine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00127 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Spermine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001256 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Synthesis routes and methods I
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Synthesis routes and methods II
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Synthesis routes and methods III
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Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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