4alpha-PDD

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 561549

CAS#: 27536-56-7

Description: 4alpha-PDD is a negative control for Phorbol-12,13-didecanoate (PDD) and Phorbol-12-myristate-13-acetate (PMA). Though it is inactive for signaling through PKC, 4alpha-PDD has been shown to activate transient receptor potential vanilloid 4 (TRPV4) channels.


Price and Availability

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4alpha-PDD is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 561549
Name: 4alpha-PDD
CAS#: 27536-56-7
Chemical Formula: C40H64O8
Exact Mass: 672.4601
Molecular Weight: 672.94
Elemental Analysis: C, 71.39; H, 9.59; O, 19.02


Synonym: 4alpha-PDD; 4alpha PDD; 4alphaPDD; 4α-Phorbol 12,13-didecanoate;

IUPAC/Chemical Name: 4alpha-Phorbol 12,13-Didecanoate

InChi Key: DGOSGFYDFDYMCW-MWRBZVGOSA-N

InChi Code: InChI=1S/C40H64O8/c1-7-9-11-13-15-17-19-21-32(42)47-36-28(4)39(46)30(24-29(26-41)25-38(45)31(39)23-27(3)35(38)44)34-37(5,6)40(34,36)48-33(43)22-20-18-16-14-12-10-8-2/h23-24,28,30-31,34,36,41,45-46H,7-22,25-26H2,1-6H3/t28-,30+,31-,34-,36-,38-,39-,40-/m1/s1

SMILES Code: OCC1=C[C@@]2([H])[C@H](C3(C)C)[C@@]3(OC(CCCCCCCCC)=O)[C@H](OC(CCCCCCCCC)=O)[C@@H](C)[C@@]2([C@@]([H])([C@@]4(C1)O)C=C(C4=O)C)O


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

1: Chen CK, Hsu PY, Wang TM, Miao ZF, Lin RT, Juo SH. TRPV4 Activation Contributes Functional Recovery from Ischemic Stroke via Angiogenesis and Neurogenesis. Mol Neurobiol. 2017 Jun 9. doi: 10.1007/s12035-017-0625-0. [Epub ahead of print] PubMed PMID: 28597396.

2: Kamakura T, Kondo M, Koyama Y, Hanada Y, Ishida Y, Nakamura Y, Yamada T, Takimoto Y, Kitahara T, Ozono Y, Horii A, Imai T, Inohara H, Shimada S. Functional Expression of an Osmosensitive Cation Channel, Transient Receptor Potential Vanilloid 4, in Rat Vestibular Ganglia. Audiol Neurootol. 2016;21(4):268-274. Epub 2016 Oct 6. PubMed PMID: 27705979.

3: Hong Z, Tian Y, Qi M, Li Y, Du Y, Chen L, Liu W, Chen L. Transient Receptor Potential Vanilloid 4 Inhibits γ-Aminobutyric Acid-Activated Current in Hippocampal Pyramidal Neurons. Front Mol Neurosci. 2016 Aug 26;9:77. doi: 10.3389/fnmol.2016.00077. eCollection 2016. PubMed PMID: 27616980; PubMed Central PMCID: PMC4999446.

4: Qu YJ, Zhang X, Fan ZZ, Huai J, Teng YB, Zhang Y, Yue SW. Effect of TRPV4-p38 MAPK Pathway on Neuropathic Pain in Rats with Chronic Compression of the Dorsal Root Ganglion. Biomed Res Int. 2016;2016:6978923. doi: 10.1155/2016/6978923. Epub 2016 Jun 5. PubMed PMID: 27366753; PubMed Central PMCID: PMC4913001.

5: Gu QD, Moss CR 2nd, Kettelhut KL, Gilbert CA, Hu H. Activation of TRPV4 Regulates Respiration through Indirect Activation of Bronchopulmonary Sensory Neurons. Front Physiol. 2016 Feb 29;7:65. doi: 10.3389/fphys.2016.00065. eCollection 2016. PubMed PMID: 26973533; PubMed Central PMCID: PMC4770051.

6: Du J, Wang X, Li J, Guo J, Liu L, Yan D, Yang Y, Li Z, Zhu J, Shen B. Increasing TRPV4 expression restores flow-induced dilation impaired in mesenteric arteries with aging. Sci Rep. 2016 Mar 7;6:22780. doi: 10.1038/srep22780. PubMed PMID: 26947561; PubMed Central PMCID: PMC4780030.

7: Ishikura T, Suzuki H, Shoguchi K, Koreeda Y, Aritomi T, Matsuura T, Yoshimura M, Ohkubo J, Maruyama T, Kawasaki M, Ohnishi H, Sakai A, Mizuno A, Suzuki M, Ueta Y. Possible involvement of TRPV1 and TRPV4 in nociceptive stimulation- induced nocifensive behavior and neuroendocrine response in mice. Brain Res Bull. 2015 Sep;118:7-16. doi: 10.1016/j.brainresbull.2015.08.004. Epub 2015 Aug 24. PubMed PMID: 26314785.

8: Qi Y, Li Z, Kong CW, Tang NL, Huang Y, Li RA, Yao X. Uniaxial cyclic stretch stimulates TRPV4 to induce realignment of human embryonic stem cell-derived cardiomyocytes. J Mol Cell Cardiol. 2015 Oct;87:65-73. doi: 10.1016/j.yjmcc.2015.08.005. Epub 2015 Aug 7. PubMed PMID: 26259779.

9: Son GY, Yang YM, Park WS, Chang I, Shin DM. Hypotonic stress induces RANKL via transient receptor potential melastatin 3 (TRPM3) and vaniloid 4 (TRPV4) in human PDL cells. J Dent Res. 2015 Mar;94(3):473-81. doi: 10.1177/0022034514567196. Epub 2015 Jan 16. PubMed PMID: 25595364; PubMed Central PMCID: PMC4814022.

10: Wang J, Wang XW, Zhang Y, Yin CP, Yue SW. Ca(2+) influx mediates the TRPV4-NO pathway in neuropathic hyperalgesia following chronic compression of the dorsal root ganglion. Neurosci Lett. 2015 Feb 19;588:159-65. doi: 10.1016/j.neulet.2015.01.010. Epub 2015 Jan 6. PubMed PMID: 25575793.

11: Hong Z, Jie P, Tian Y, Chen T, Chen L, Chen L. Transient Receptor Potential Vanilloid 4-Induced Modulation of Voltage-Gated Sodium Channels in Hippocampal Neurons. Mol Neurobiol. 2016 Jan;53(1):759-768. doi: 10.1007/s12035-014-9038-5. Epub 2014 Dec 15. PubMed PMID: 25502461.

12: Klausen TK, Janssens A, Prenen J, Owsianik G, Hoffmann EK, Pedersen SF, Nilius B. Single point mutations of aromatic residues in transmembrane helices 5 and -6 differentially affect TRPV4 activation by 4α-PDD and hypotonicity: implications for the role of the pore region in regulating TRPV4 activity. Cell Calcium. 2014 Jan;55(1):38-47. doi: 10.1016/j.ceca.2013.11.001. Epub 2013 Nov 21. PubMed PMID: 24342753.

13: Sukumaran SV, Singh TU, Parida S, Narasimha Reddy ChE, Thangamalai R, Kandasamy K, Singh V, Mishra SK. TRPV4 channel activation leads to endothelium-dependent relaxation mediated by nitric oxide and endothelium-derived hyperpolarizing factor in rat pulmonary artery. Pharmacol Res. 2013 Dec;78:18-27. doi: 10.1016/j.phrs.2013.09.005. Epub 2013 Sep 25. PubMed PMID: 24075884.

14: Ning L, Wang C, Fan X, Ding X, Wang Y, Zhang Y, Wang J, Yue S. Role of colchicine-induced microtubule depolymerization in hyperalgesia via TRPV4 in rats with chronic compression of the dorsal root ganglion. Neurol Res. 2014 Jan;36(1):70-8. doi: 10.1179/1743132813Y.0000000261. Epub 2013 Dec 6. PubMed PMID: 24074178.

15: Skrzypski M, Kakkassery M, Mergler S, Grötzinger C, Khajavi N, Sassek M, Szczepankiewicz D, Wiedenmann B, Nowak KW, Strowski MZ. Activation of TRPV4 channel in pancreatic INS-1E beta cells enhances glucose-stimulated insulin secretion via calcium-dependent mechanisms. FEBS Lett. 2013 Oct 1;587(19):3281-7. doi: 10.1016/j.febslet.2013.08.025. Epub 2013 Aug 30. PubMed PMID: 23999312.

16: Li L, Yin J, Jie PH, Lu ZH, Zhou LB, Chen L, Chen L. Transient receptor potential vanilloid 4 mediates hypotonicity-induced enhancement of synaptic transmission in hippocampal slices. CNS Neurosci Ther. 2013 Nov;19(11):854-62. doi: 10.1111/cns.12143. Epub 2013 Jul 4. PubMed PMID: 23826708.

17: Ma X, Du J, Zhang P, Deng J, Liu J, Lam FF, Li RA, Huang Y, Jin J, Yao X. Functional role of TRPV4-KCa2.3 signaling in vascular endothelial cells in normal and streptozotocin-induced diabetic rats. Hypertension. 2013 Jul;62(1):134-9. doi: 10.1161/HYPERTENSIONAHA.113.01500. Epub 2013 May 6. PubMed PMID: 23648706.

18: Wang Y, Ding M, Chaudhari S, Ding Y, Yuan J, Stankowska D, He S, Krishnamoorthy R, Cunningham JT, Ma R. Nuclear factor κB mediates suppression of canonical transient receptor potential 6 expression by reactive oxygen species and protein kinase C in kidney cells. J Biol Chem. 2013 May 3;288(18):12852-65. doi: 10.1074/jbc.M112.410357. Epub 2013 Mar 22. PubMed PMID: 23525112; PubMed Central PMCID: PMC3642329.

19: Li L, Qu W, Zhou L, Lu Z, Jie P, Chen L, Chen L. Activation of Transient Receptor Potential Vanilloid 4 Increases NMDA-Activated Current in Hippocampal Pyramidal Neurons. Front Cell Neurosci. 2013 Mar 4;7:17. doi: 10.3389/fncel.2013.00017. eCollection 2013. Erratum in: Front Cell Neurosci. 2014;8:130. Dosage error in published abstract; MEDLINE/PubMed abstract corrected. PubMed PMID: 23459987; PubMed Central PMCID: PMC3586694.

20: O'Mullane LM, Keast JR, Osborne PB. Co-cultures provide a new tool to probe communication between adult sensory neurons and urothelium. J Urol. 2013 Aug;190(2):737-45. doi: 10.1016/j.juro.2013.01.048. Epub 2013 Jan 23. PubMed PMID: 23353045; PubMed Central PMCID: PMC4630218.