≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
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
| Sourires canoniques | 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 |
| Isomères 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 |
| Termes d'entrée MeSH | (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 |
| Poids moléculaire | 909.08 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Classe | 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 |
| Description | 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 |
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| Solubilité | DMSO : 33.33 mg/mL (36.66 mM; ultrasonic and warming and heat to 60°C) H2O : <0.1 mg/mL (ultrasonic) (insoluble) |
|---|---|
| Poids moléculaire | 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 |
