From Wikipedia, the free encyclopedia
Phenylacetylrinvanil
Identifiers
  • [(Z,7R)-18-[(4-Hydroxy-3-methoxyphenyl)methylamino]-18-oxooctadec-9-en-7-yl] 2-phenylacetate
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC34H49NO5
Molar mass551.768 g·mol−1
3D model ( JSmol)
  • CCCCCC[C@H](C/C=C\CCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC)OC(=O)CC2=CC=CC=C2
  • InChI=1S/C34H49NO5/c1-3-4-5-15-20-30(40-34(38)26-28-18-13-12-14-19-28)21-16-10-8-6-7-9-11-17-22-33(37)35-27-29-23-24-31(36)32(25-29)39-2/h10,12-14,16,18-19,23-25,30,36H,3-9,11,15,17,20-22,26-27H2,1-2H3,(H,35,37)/b16-10-/t30-/m1/s1
  • Key:LXLBUUJANYSIKU-DJVRBGHSSA-N

Phenylacetylrinvanil (IDN-5890) is a synthetic analogue of capsaicin which acts as a potent and selective agonist for the TRPV1 receptor, with slightly lower potency than resiniferatoxin, though still around 300 times the potency of capsaicin. It is an amide of vanillylamine and ricinoleic acid, with the hydroxyl group on ricinoleic acid esterified with phenylacetic acid. It is used to study the function of the TRPV1 receptor and its downstream actions, and has also shown anti-cancer effects in vitro. [1] [2] [3]

References

  1. ^ Appendino G, De Petrocellis L, Trevisani M, Minassi A, Daddario N, Moriello AS, et al. (February 2005). "Development of the first ultra-potent "capsaicinoid" agonist at transient receptor potential vanilloid type 1 (TRPV1) channels and its therapeutic potential". The Journal of Pharmacology and Experimental Therapeutics. 312 (2): 561–70. doi: 10.1124/jpet.104.074864. PMID  15356216. S2CID  816699.
  2. ^ Luviano A, Aguiñiga-Sánchez I, Demare P, Tiburcio R, Ledesma-Martínez E, Santiago-Osorio E, Regla I (May 2014). "Antineoplastic activity of rinvanil and phenylacetylrinvanil in leukaemia cell lines". Oncology Letters. 7 (5): 1651–1656. doi: 10.3892/ol.2014.1958. PMC  3997731. PMID  24765194.
  3. ^ Sánchez-Sánchez L, Alvarado-Sansininea JJ, Escobar ML, López-Muñoz H, Hernández-Vázquez JM, Monsalvo-Montiel I, et al. (July 2015). "Evaluation of the antitumour activity of Rinvanil and Phenylacetylrinvanil on the cervical cancer tumour cell lines HeLa, CaSKi and ViBo". European Journal of Pharmacology. 758: 129–36. doi: 10.1016/j.ejphar.2015.04.003. PMID  25864613.


From Wikipedia, the free encyclopedia
Phenylacetylrinvanil
Identifiers
  • [(Z,7R)-18-[(4-Hydroxy-3-methoxyphenyl)methylamino]-18-oxooctadec-9-en-7-yl] 2-phenylacetate
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC34H49NO5
Molar mass551.768 g·mol−1
3D model ( JSmol)
  • CCCCCC[C@H](C/C=C\CCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC)OC(=O)CC2=CC=CC=C2
  • InChI=1S/C34H49NO5/c1-3-4-5-15-20-30(40-34(38)26-28-18-13-12-14-19-28)21-16-10-8-6-7-9-11-17-22-33(37)35-27-29-23-24-31(36)32(25-29)39-2/h10,12-14,16,18-19,23-25,30,36H,3-9,11,15,17,20-22,26-27H2,1-2H3,(H,35,37)/b16-10-/t30-/m1/s1
  • Key:LXLBUUJANYSIKU-DJVRBGHSSA-N

Phenylacetylrinvanil (IDN-5890) is a synthetic analogue of capsaicin which acts as a potent and selective agonist for the TRPV1 receptor, with slightly lower potency than resiniferatoxin, though still around 300 times the potency of capsaicin. It is an amide of vanillylamine and ricinoleic acid, with the hydroxyl group on ricinoleic acid esterified with phenylacetic acid. It is used to study the function of the TRPV1 receptor and its downstream actions, and has also shown anti-cancer effects in vitro. [1] [2] [3]

References

  1. ^ Appendino G, De Petrocellis L, Trevisani M, Minassi A, Daddario N, Moriello AS, et al. (February 2005). "Development of the first ultra-potent "capsaicinoid" agonist at transient receptor potential vanilloid type 1 (TRPV1) channels and its therapeutic potential". The Journal of Pharmacology and Experimental Therapeutics. 312 (2): 561–70. doi: 10.1124/jpet.104.074864. PMID  15356216. S2CID  816699.
  2. ^ Luviano A, Aguiñiga-Sánchez I, Demare P, Tiburcio R, Ledesma-Martínez E, Santiago-Osorio E, Regla I (May 2014). "Antineoplastic activity of rinvanil and phenylacetylrinvanil in leukaemia cell lines". Oncology Letters. 7 (5): 1651–1656. doi: 10.3892/ol.2014.1958. PMC  3997731. PMID  24765194.
  3. ^ Sánchez-Sánchez L, Alvarado-Sansininea JJ, Escobar ML, López-Muñoz H, Hernández-Vázquez JM, Monsalvo-Montiel I, et al. (July 2015). "Evaluation of the antitumour activity of Rinvanil and Phenylacetylrinvanil on the cervical cancer tumour cell lines HeLa, CaSKi and ViBo". European Journal of Pharmacology. 758: 129–36. doi: 10.1016/j.ejphar.2015.04.003. PMID  25864613.



Videos

Youtube | Vimeo | Bing

Websites

Google | Yahoo | Bing

Encyclopedia

Google | Yahoo | Bing

Facebook