5-(N,N-Hexamethylene)amiloride - Moligand™, ≥98% , Allosteric modulator of α 2A-adrenoceptor;Allosteric modulator of GnRH 1 receptor, CAS No.1428-95-1, Allosteric modulator of α 2A-adrenoceptor;Allosteric modulator of GnRH 1 receptor

CAS: 1428-95-1 Cat. No.: N341740 Molecular Weight: 311.77 EC Number: 634-319-7

GRADE & PURITY Moligand™, ≥98%

Synonyms

3-amino-5-(azepan-1-yl)-N-carbamimidoyl-6-chloropyrazine-2-carboxamide | NCGC00015108-06 | Spectrum2_001669 | Spectrum3_001662 | CHEBI:76400 | NCGC00015108-09 | NCGC00015108-03 | NCGC00093601-02 | SCHEMBL9852488 | 3-amino-5-(azepan-1-yl)-6-chloro-N-(diami

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

3-amino-5-(azepan-1-yl)-N-carbamimidoyl-6-chloropyrazine-2-carboxamide | NCGC00015108-06 | Spectrum2_001669 | Spectrum3_001662 | CHEBI:76400 | NCGC00015108-09 | NCGC00015108-03 | NCGC00093601-02 | SCHEMBL9852488 | 3-amino-5-(azepan-1-yl)-6-chloro-N-(diami

Specifications & Purity

Moligand™, ≥98%

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ALLOSTERIC MODULATOR

Mechanism of action

Allosteric modulator of α 2A-adrenoceptor;Allosteric modulator of GnRH 1 receptor

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1CCCN(CC1)C2=NC(=C(N=C2Cl)C(=O)N=C(N)N)N
• IUPAC Name: 3-amino-5-(azepan-1-yl)-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide
• InChIKey: RQQJJXVETXFINY-UHFFFAOYSA-N
• INCHI: 1S/C12H18ClN7O/c13-8-10(20-5-3-1-2-4-6-20)18-9(14)7(17-8)11(21)19-12(15)16/h1-6H2,(H2,14,18)(H4,15,16,19,21)
• Isomeric SMILES: C1CCCN(CC1)C2=NC(=C(N=C2Cl)C(=O)N=C(N)N)N
• WGK Germany: 3
• Alternate CAS: 1428-95-1
• MeSH Entry Terms: 3-amino-6-chloro-5-(1-homopiperidyl)-N-(diaminomethylene)pyrazinecarboxamide;5-(N,N-hexamethylene)amiloride;5-HMA;hexamethylene amiloride;hexamethyleneamiloride;HMA-5
• Molecular Weight: 311.77
• Reaxy-Rn: 8579364
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8579364&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazines
      • Subclass Pyrazines
        • Level5 Pyrazine carboxylic acids and derivatives
          • Level6 Pyrazinecarboxamides

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazines
• Subclass: Pyrazines
• Intermediate Tree Nodes: Pyrazine carboxylic acids and derivatives
• Direct Parent: Pyrazinecarboxamides
• Alternative Parents: Dialkylarylamines Acylguanidines Aminopyrazines Azepanes Aryl chlorides Imidolactams Vinylogous amides Heteroaromatic compounds Amino acids and derivatives Propargyl-type 1,3-dipolar organic compounds Azacyclic compounds Carboximidamides Hydrocarbon derivatives Organic oxides Organochlorides Organooxygen compounds Organopnictogen compounds Primary amines
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyrazinecarboxamide - Dialkylarylamine - Acylguanidine - Aminopyrazine - Azepane - Aryl chloride - Aryl halide - Imidolactam - Heteroaromatic compound - Vinylogous amide - Amino acid or derivatives - Guanidine - Azacycle - Organic 1,3-dipolar compound - Carboxylic acid derivative - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Organochloride - Organohalogen compound - Amine - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Primary amine - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrazinecarboxamides. These are compounds containing a pyrazine ring which bears a carboxamide.
• External Descriptors: pyrazines - monocarboxylic acid amide - organochlorine compound - guanidines - aromatic amine - azepanes

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CYP1A2 Tchem Cytochrome P450 1A2 (1 Activities)

Discover Target: CYP1A2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC9A5 Tchem Sodium/hydrogen exchanger 5 (4 Activities)

Discover Target: SLC9A5

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ADRA2A Tclin Alpha-2A adrenergic receptor (1 Activities)

Discover Target: ADRA2A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

KCNH2 Tclin Potassium voltage-gated channel subfamily H member 2 (1 Activities)

Discover Target: KCNH2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GNRHR Tclin Gonadotropin-releasing hormone receptor (1 Activities)

Discover Target: GNRHR

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

F2 Tclin Thrombin (11687 Activities)

Discover Target: F2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PLG Tclin Plasminogen (2339 Activities)

Discover Target: PLG

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KLKB1 Tclin Plasma kallikrein (2047 Activities)

Discover Target: KLKB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SCNN1A Tclin Amiloride-sensitive sodium channel alpha-subunit (48 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

F10 Tclin Coagulation factor X (9693 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TRPV1 Tclin Vanilloid receptor (8273 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ARSA Tbio Cerebroside-sulfatase (655 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

F11 Tchem Coagulation factor XI (1733 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PLAT Tclin Tissue-type plasminogen activator (1057 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SCN5A Tclin Sodium channel protein type V alpha subunit (3462 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SMPD1 Tchem Sphingomyelin phosphodiesterase (13561 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PLAU Tchem Urokinase-type plasminogen activator (2016 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC9A3 Tclin Sodium/hydrogen exchanger 3 (483 Activities)

Discover Target: SLC9A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC9A5 Tchem Sodium/hydrogen exchanger 5 (22 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PROC Tchem Vitamin K-dependent protein C (491 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HT-1080 (3966 Activities)

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SH-SY5Y (11521 Activities)

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HEK293 (82097 Activities)

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HepG2 (196354 Activities)

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MDA-MB-231 (73002 Activities)

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FEN1 Tchem Flap endonuclease 1 (12055 Activities)

Discover Target: FEN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ASIC3 Tchem Amiloride-sensitive cation channel 3 (217 Activities)

Discover Target: ASIC3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

Discover Target: KDM4A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LMNA Tbio Prelamin-A/C (36751 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

THPO Tbio Thrombopoietin (834 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NPC1 Tchem Niemann-Pick C1 protein (18985 Activities)

Discover Target: NPC1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RAB9A Tbio Ras-related protein Rab-9A (22488 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MBNL1 Tbio Muscleblind-like protein 1 (34431 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SCNN1B Tclin Amiloride-sensitive sodium channel subunit beta (6 Activities)

Discover Target: SCNN1B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SCNN1G Tclin Amiloride-sensitive sodium channel subunit gamma (6 Activities)

Discover Target: SCNN1G

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

Discover Target: ampC

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trypsin (394 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC9A1 Sodium/hydrogen exchanger 1 (3 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Plasmodium falciparum (966862 Activities)

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Rattus norvegicus (775804 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PYK Pyruvate kinase (6726 Activities)

Discover Target: PYK

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pfk 6-phospho-1-fructokinase (7870 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FTL Ferritin light chain (43324 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

nfo Endonuclease 4 (425 Activities)

Discover Target: nfo

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Adora2b Adenosine A2 receptor (1828 Activities)

Discover Target: Adora2b

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in 0.1N Hydrochloric Acid: 20 mg/ml
• Molecular Weight: 311.770 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 311.126 Da
• Monoisotopic Mass: 311.126 Da
• Topological Polar Surface Area: 137.000 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 393.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yang Gao, Kunming Li, Xiuyan Ren, Guanghui Gao.  (2023)  Thermochromic Hydrogels with Opaque-Transparent Gradient Transition for Switchable Window and Temperature Monitor.  CHEMISTRY-A EUROPEAN JOURNAL,      [PMID:37584162] [10.1002/chem.202302147]

2. Xiuhua Sun, Shanshan Pan, Zhiren Guo, Yingxin Cui, Liang Ma, Xiaosong Yu, Taijiang Gui, Shougang Chen, Yan Liu, Changlu Gao.  (2023)  Synergy effect of bactericidal and antifouling with structure reversion and hydrolysis of cationic amphiphilic copolymer PHMA-b-PCBMAE to zwitterionic copolymer.  PROGRESS IN ORGANIC COATINGS,      [PMID:] [10.1016/j.porgcoat.2023.107508]

3. Liang YaoYao, Luo Juan, Yang Chenhao, Guo Shuning, Zhang Bowen, Chen Fengqianrui, Su Kairui, Zhang Yulong, Dong Yi, Wang Zhihao, Fu Hongda, Sui Guangchao, Wang Pengchao.  (2022)  Directed evolution of the PobR allosteric transcription factor to generate a biosensor for 4-hydroxymandelic acid.  WORLD JOURNAL OF MICROBIOLOGY & BIOTECHNOLOGY,  38  (6): (1-10).  [PMID:35501522] [10.1007/s11274-022-03286-5]

4. Haiquan Zhang, Zijing Liu, Junping Mai, Ning Wang, Jie Zhong, Xianmin Mai, Nan Zhang.  (2021)  Super-elastic smart phase change material (SPCM) for thermal energy storage.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2021.128482]

5. Kunming Li, Shengfei Meng, Shan Xia, Xiuyan Ren, Guanghui Gao.  (2020)  Durable and Controllable Smart Windows Based on Thermochromic Hydrogels.  ACS Applied Materials & Interfaces,      [PMID:32820627] [10.1021/acsami.0c12710]

6. Yaxin Hu, Xiaoqin Liang, Dongliang Wu, Bang Yu, Yijia Wang, Yifang Mi, Zhihai Cao, Zujin Zhao.  (2019)  Towards white-light emission of fluorescent polymeric nanoparticles with a single luminogen possessing AIE and TICT properties.  Journal of Materials Chemistry C,  8  (2): (734-741).  [PMID:] [10.1039/C9TC05690D]

7. Li Liu, Guangchao Lv, Xiuyan Ren, Xinhe Li, Te Wang, Jingwen Dong, Zeyu Wang, Guangfeng Wu.  (2019)  Effect of size of latex particles on the mechanical properties of hydrogels reinforced by latex particles.  RSC Advances,  9  (26): (14701-14707).  [PMID:35516310] [10.1039/C9RA01688K]

8. Zheng Li, Jianding Chen, Guijin Zou, Tongyuan Zhang, Dafu Wei, Xiang Xu, Yong Guan, Anna Zheng.  (2019)  Anionic living polymerization of alkyl methacrylate at ambient temperature and its mechanism research.  JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY,  57  (10): (1130-1139).  [PMID:] [10.1002/pola.29368]

9. Mingfu Li, Pingjun Zhang, Shuanglan Hu, Douyong Min, Jingjie Tang, Yingchuan Zhang, Liqun Jiang.  (2025)  Efficient synthesis of 5-hydroxylmethxylfufrual from fructose in a phenolic acid-derived ternary deep eutectic solvent.  FUEL,      [PMID:] [10.1016/j.fuel.2025.134548]

10. Li Liu, Xinhe Li, Xiuyan Ren, Guang feng Wu.  (2020)  Flexible strain sensors with rapid self-healing by multiple hydrogen bonds.  POLYMER,      [PMID:] [10.1016/j.polymer.2020.122657]