WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H565266
CAS#: 33281-81-1
Description: Peridinin is an exceptionally potent and membrane-embedded inhibitor of bilayer lipid peroxidation.
Hodoodo Cat#: H565266
Name: Peridinin
CAS#: 33281-81-1
Chemical Formula: C39H50O7
Exact Mass: 630.36
Molecular Weight: 630.820
Elemental Analysis: C, 74.26; H, 7.99; O, 17.75
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Synonym: Peridinin; NSC-679586; NSC 679586; NSC679586
IUPAC/Chemical Name: [(1S,3R)-3-Hydroxy-4-[(3E,5E,7E,9E,11Z)-11-[4-[(E)-2-[(1R,3S,6S)-3-hydroxy-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl]ethenyl]-5-oxofuran-2-ylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaenylidene]-3,5,5-trimethylcyclohexyl] acetate
InChi Key: UYRDHEJRPVSJFM-VSWVFQEASA-N
InChi Code: InChI=1S/C39H50O7/c1-26(16-17-33-35(4,5)24-32(44-28(3)40)25-37(33,8)43)14-12-10-11-13-15-27(2)20-31-21-29(34(42)45-31)18-19-39-36(6,7)22-30(41)23-38(39,9)46-39/h10-16,18-21,30,32,41,43H,22-25H2,1-9H3/b12-10+,13-11+,19-18+,26-14+,27-15+,31-20-/t17?,30-,32-,37+,38+,39-/m0/s1
SMILES Code: CC(O[C@@H]1C[C@@](C)(O)C(C(C)(C)C1)=C=C/C(C)=C/C=C/C=C/C=C(C)/C=C(C=C2/C=C/[C@]34C(C)(C)C[C@H](O)C[C@@]3(C)O4)\OC2=O)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 630.82 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Ueba Y, Aratake T, Onodera KI, Higashi Y, Hamada T, Shimizu T, Shimizu S, Yawata T, Nakamura R, Akizawa T, Ueba T, Saito M. Attenuation of zinc-enhanced inflammatory M1 phenotype of microglia by peridinin protects against short-term spatial-memory impairment following cerebral ischemia in mice. Biochem Biophys Res Commun. 2018 Dec 9;507(1-4):476-483. doi: 10.1016/j.bbrc.2018.11.067. Epub 2018 Nov 19. PubMed PMID: 30466781.
2: Haley HMS, Hill AG, Greenwood AI, Woerly EM, Rienstra CM, Burke MD. Peridinin Is an Exceptionally Potent and Membrane-Embedded Inhibitor of Bilayer Lipid Peroxidation. J Am Chem Soc. 2018 Nov 14;140(45):15227-15240. doi: 10.1021/jacs.8b06933. Epub 2018 Nov 2. PubMed PMID: 30388000; PubMed Central PMCID: PMC6452872.
3: Agostini A, Niklas J, Schulte T, Di Valentin M, Bortolus M, Hofmann E, Lubitz W, Carbonera D. Changing the site energy of per-614 in the Peridinin-chlorophyll a-protein does not alter its capability of chlorophyll triplet quenching. Biochim Biophys Acta Bioenerg. 2018 Aug;1859(8):612-618. doi: 10.1016/j.bbabio.2018.05.008. Epub 2018 May 19. PubMed PMID: 29782823.
4: Taffet EJ, Scholes GD. Peridinin Torsional Distortion and Bond-Length Alternation Introduce Intramolecular Charge-Transfer and Correlated Triplet Pair Intermediate Excited States. J Phys Chem B. 2018 Jun 7;122(22):5835-5844. doi: 10.1021/acs.jpcb.8b02504. Epub 2018 May 24. PubMed PMID: 29757643.
5: Niedzwiedzki DM, Blankenship RE. Excited-state properties of the central-cis isomer of the carotenoid peridinin. Arch Biochem Biophys. 2018 Jul 1;649:29-36. doi: 10.1016/j.abb.2018.05.004. Epub 2018 May 6. PubMed PMID: 29742456.
6: Kaminska I, Bohlen J, Mackowski S, Tinnefeld P, Acuna GP. Strong Plasmonic Enhancement of a Single Peridinin-Chlorophyll a-Protein Complex on DNA Origami-Based Optical Antennas. ACS Nano. 2018 Feb 27;12(2):1650-1655. doi: 10.1021/acsnano.7b08233. Epub 2018 Jan 29. PubMed PMID: 29353479.
7: Greco JA, Wagner NL, Frank HA, Birge RR. The Forbidden 1(1)B(u)(-) Excited Singlet State in Peridinin and Peridinin Analogues. J Phys Chem A. 2018 Jan 11;122(1):130-139. doi: 10.1021/acs.jpca.7b10001. Epub 2017 Dec 19. PubMed PMID: 29202230.
8: Redeckas K, Voiciuk V, Zigmantas D, Hiller RG, Vengris M. Unveiling the excited state energy transfer pathways in peridinin-chlorophyll a-protein by ultrafast multi-pulse transient absorption spectroscopy. Biochim Biophys Acta Bioenerg. 2017 Apr;1858(4):297-307. doi: 10.1016/j.bbabio.2017.01.014. Epub 2017 Feb 2. PubMed PMID: 28161327.
9: Ghosh S, Bishop MM, Roscioli JD, LaFountain AM, Frank HA, Beck WF. Excitation Energy Transfer by Coherent and Incoherent Mechanisms in the Peridinin-Chlorophyll a Protein. J Phys Chem Lett. 2017 Jan 19;8(2):463-469. doi: 10.1021/acs.jpclett.6b02881. Epub 2017 Jan 9. PubMed PMID: 28042923.
10: Dorrell RG, Klinger CM, Newby RJ, Butterfield ER, Richardson E, Dacks JB, Howe CJ, Nisbet ER, Bowler C. Progressive and Biased Divergent Evolution Underpins the Origin and Diversification of Peridinin Dinoflagellate Plastids. Mol Biol Evol. 2017 Feb 1;34(2):361-379. doi: 10.1093/molbev/msw235. PubMed PMID: 27816910.
11: Ghosh S, Roscioli JD, Bishop MM, Gurchiek JK, LaFountain AM, Frank HA, Beck WF. Correction to "Torsional Dynamics and Intramolecular Charge Transfer in the S(2) (1(1)B(u)(+)) Excited State of Peridinin: A Mechanism for Enhanced Mid-Visible Light Harvesting". J Phys Chem Lett. 2016 Nov 17;7(22):4596. Epub 2016 Nov 2. PubMed PMID: 27804301.
12: Di Valentin M, Dal Farra MG, Galazzo L, Albertini M, Schulte T, Hofmann E, Carbonera D. Distance measurements in peridinin-chlorophyll a-protein by light-induced PELDOR spectroscopy. Analysis of triplet state localization. Biochim Biophys Acta. 2016 Dec;1857(12):1909-1916. doi: 10.1016/j.bbabio.2016.09.008. Epub 2016 Sep 20. PubMed PMID: 27659505.
13: Ghosh S, Roscioli JD, Bishop MM, Gurchiek JK, LaFountain AM, Frank HA, Beck WF. Torsional Dynamics and Intramolecular Charge Transfer in the S2 (1(1)Bu(+)) Excited State of Peridinin: A Mechanism for Enhanced Mid-Visible Light Harvesting. J Phys Chem Lett. 2016 Sep 15;7(18):3621-6. doi: 10.1021/acs.jpclett.6b01642. Epub 2016 Sep 1. PubMed PMID: 27571487.
14: Ishikawa C, Jomori T, Tanaka J, Senba M, Mori N. Peridinin, a carotenoid, inhibits proliferation and survival of HTLV-1-infected T-cell lines. Int J Oncol. 2016 Oct;49(4):1713-21. doi: 10.3892/ijo.2016.3648. Epub 2016 Aug 4. PubMed PMID: 27499015.
15: Ghosh S, Bishop MM, Roscioli JD, LaFountain AM, Frank HA, Beck WF. Femtosecond Heterodyne Transient Grating Studies of Nonradiative Deactivation of the S2 (1(1)Bu(+)) State of Peridinin: Detection and Spectroscopic Assignment of an Intermediate in the Decay Pathway. J Phys Chem B. 2016 Apr 21;120(15):3601-14. doi: 10.1021/acs.jpcb.5b12753. Epub 2016 Apr 11. PubMed PMID: 27018823.
16: Jiang J, Zhang H, Lu X, Lu Y, Cuneo MJ, O'Neill HM, Urban V, Lo CS, Blankenship RE. Oligomerization state and pigment binding strength of the peridinin-Chl a-protein. FEBS Lett. 2015 Sep 14;589(19 Pt B):2713-9. doi: 10.1016/j.febslet.2015.07.039. Epub 2015 Aug 1. PubMed PMID: 26241331.
17: Götze JP, Karasulu B, Patil M, Thiel W. Vibrational relaxation as the driving force for wavelength conversion in the peridinin-chlorophyll a-protein. Biochim Biophys Acta. 2015 Dec;1847(12):1509-17. doi: 10.1016/j.bbabio.2015.07.011. Epub 2015 Jul 29. PubMed PMID: 26231454.
18: Di Donato M, Ragnoni E, Lapini A, Foggi P, Hiller RG, Righini R. Femtosecond transient infrared and stimulated Raman spectroscopy shed light on the relaxation mechanisms of photo-excited peridinin. J Chem Phys. 2015 Jun 7;142(21):212409. doi: 10.1063/1.4915072. PubMed PMID: 26049429.
19: Bricker WP, Lo CS. Efficient pathways of excitation energy transfer from delocalized S2 excitons in the peridinin-chlorophyll a-protein complex. J Phys Chem B. 2015 May 7;119(18):5755-64. doi: 10.1021/jp511766j. Epub 2015 Apr 22. PubMed PMID: 25866867.
20: PLOS ONE Staff. Correction: Separate Introns Gained within Short and Long Soluble Peridinin-Chlorophyll a-Protein Genes during Radiation of Symbiodinium (Dinophyceae) Clade A and B Lineages. PLoS One. 2015 Jan 21;10(1):e0117735. doi: 10.1371/journal.pone.0117735. eCollection 2015. PubMed PMID: 25608022; PubMed Central PMCID: PMC4301918.
