Diprovocim - ≥98% , CAS No.2170867-89-5

CAS: 2170867-89-5 Cat. No.: D647537 Summenformel: C₅₆H₅₆N₆O₆ Molekulargewicht: 909.08 PubChem CID: 137553173

GRADE & PURITY ≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

Diprovocim is a potent TLR1/TLR2 agonist. Diprovocim elicits full agonist activity in human THP-1 cells (EC 50 =110 pM). Diprovocim stimulates the release of TNF-α from mouse macrophages (EC 50 =1.3 nM). Diprovocim activates downstream MAPK and NF-κB signaling pathway. Diprovocim displays strong adjuvant activity in mice, particularly abetting cellular immune responses

In Vitro

Diprovocim (5 nM in THP-1 and 500 nM in mouse peritoneal macrophage; 15-120 mins) induces phosphorylation of IKKα, IKKβ, p38, JNK, and ERK, as well as degradation of IκBα in THP-1 cells and mouse peritoneal macrophages. Diprovocim (0.01-10000 nM; 4 hours) induces dose-dependent TNF production by THP-1 cells (EC 50 =110 pM) and human peripheral blood mononuclear cells (PBMC) (EC 50 =875 pM) and by mouse peritoneal macrophages (EC 50 =1.3 nM) and bone marrow-derived dendritic cells (BMDC) (EC 50 =6.7 nM). In addition to TNF, Diprovocim induced IL-6 production by mouse BMDC. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Western Blot AnalysisCell Line: THP-1 cells and mouse peritoneal macrophages Concentration: 5 nM in THP-1 and 500 nM in mouse peritoneal macrophages Incubation Time: 15, 30, 60, 120 mins Result: Induced phosphorylation of IKKα, IKKβ, p38, JNK, and ERK, as well as degradation of IκBα.

In Vivo

Diprovocim (10 mg/kg) uses as an adjuvant and mixed with ovalbumin (OVA; 100 μg) by i.m. induces similar levels of serum OVA-specific IgG after 14 days. Diprovocim (10 mg/kg; i.m.) mixed with ovalbumin (OVA; 100 μg) before inoculation with B16-OVA cells immunizes significantly slows tumor growth rate but failed to prolong survival relative to OVA alone after 7 days. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: WT or Tlr2 −/− C57BL/6J miceDosage: 10 mg/kg Administration: IM Result: Induced similar levels of serum OVA-specific IgG, which were highly elevated compared with levels induced by immunization with OVA plus vehicle by i.m. with 100 μg OVA mixed with this drug.

Form:Solid

IC50& Target:TLR1|TLR2|p38 MAPK|NF-κB

Specifications

Spezifikationen & Reinheit

≥98%

Biochemische und physiologische Mechanismen

Diprovocim is a potent TLR1/TLR2 agonist. Diprovocim elicits full agonist activity in human THP-1 cells (EC 50 =110 pM). Diprovocim stimulates the release of TNF-α from mouse macrophages (EC 50 =1.3 nM). Diprovocim activates downstream MAPK and NF-κB sign

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Aktionsart

AGONIST

Reinheit

≥98%

Namen und Kennungen

• Kanonisches Lächeln: C1C(C1NC(=O)C2CN(CC2C(=O)NC3CC3C4=CC=CC=C4)C(=O)C5=CC=C(C=C5)C(=O)N6CC(C(C6)C(=O)NC7CC7C8=CC=CC=C8)C(=O)NC9CC9C1=CC=CC=C1)C1=CC=CC=C1
• IUPAC Name: (3S,4S)-1-[4-[(3S,4S)-3,4-bis[[(1S,2R)-2-phenylcyclopropyl]carbamoyl]pyrrolidine-1-carbonyl]benzoyl]-3-N,4-N-bis[(1S,2R)-2-phenylcyclopropyl]pyrrolidine-3,4-dicarboxamide
• InChIKey: ABZBNXFGYUSVCJ-UYMKNZQYSA-N
• INCHI: 1S/C56H56N6O6/c63-51(57-47-25-39(47)33-13-5-1-6-14-33)43-29-61(30-44(43)52(64)58-48-26-40(48)34-15-7-2-8-16-34)55(67)37-21-23-38(24-22-37)56(68)62-31-45(53(65)59-49-27-41(49)35-17-9-3-10-18-35)46(32-62)54(66)60-50-28-42(50)36-19-11-4-12-20-36/h1-24,39-50H,25-32H2,(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t39-,40-,41-,42-,43-,44-,45-,46-,47+,48+,49+,50+/m1/s1
• Isomere SMILES: C1[C@@H]([C@H]1NC(=O)[C@@H]2CN(C[C@H]2C(=O)N[C@H]3C[C@@H]3C4=CC=CC=C4)C(=O)C5=CC=C(C=C5)C(=O)N6C[C@H]([C@@H](C6)C(=O)N[C@H]7C[C@@H]7C8=CC=CC=C8)C(=O)N[C@H]9C[C@@H]9C1=CC=CC=C1)C1=CC=CC=C1
• PubChem CID: 137553173
• MeSH-Eintrag: (3R,4R)-1-(4-((3R,4R)-3,4-bis(((1R,2S)-2-phenylcyclopropyl)carbamoyl)pyrrolidine-1-carbonyl)benzoyl)-3-N,4-N-bis((1R,2S)-2-phenylcyclopropyl)pyrrolidine-3,4-dicarboxamide;diprovocim
• Molekulargewicht: 909.08

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzamides
• Alternative Parents: Pyrrolidinecarboxamides N-acylpyrrolidines Benzoyl derivatives Tertiary carboxylic acid amides Secondary carboxylic acid amides Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Benzamide - Pyrrolidine-3-carboxamide - Pyrrolidine carboxylic acid or derivatives - N-acylpyrrolidine - Benzoyl - Tertiary carboxylic acid amide - Pyrrolidine - Secondary carboxylic acid amide - Carboxamide group - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic heteromonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.
• External Descriptors: Not available

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

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TLR2 Tchem Toll-like receptor 2 (1 Activities)

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

TLR2 Tchem Toll-like receptor 2 (975 Activities)

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

TLR2 Tchem Toll-like receptor 1/2 (401 Activities)

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Mus musculus (284745 Activities)

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Splenocyte (1641 Activities)

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Tlr1 Toll-like receptor 1 (1 Activities)

Discover Target: Tlr1

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Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Löslichkeit: DMSO : 33.33 mg/mL (36.66 mM; ultrasonic and warming and heat to 60°C) H2O : <0.1 mg/mL (ultrasonic) (insoluble)
• Molekulargewicht: 909.100 g/mol
• XLogP3: 5.300
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 14
• Exact Mass: 908.426 Da
• Monoisotopic Mass: 908.426 Da
• Topological Polar Surface Area: 157.000 Ų
• Heavy Atom Count: 68
• Formal Charge: 0
• Complexity: 1620.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 12
• 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