Dauricine

Dauricine
Names
IUPAC name
4-{[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-2-(4-{[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenoxy)phenol
Identifiers
524-17-4
3D model (Jmol) Interactive image
ChEBI CHEBI:4331
ChEMBL ChEMBL442717
ChemSpider 66117
ECHA InfoCard 100.208.622
PubChem 73400
Properties
C38H44N2O6
Molar mass 624.76576
Density 1.186 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dauricine is a plant metabolite, chemically classified as a phenol, an aromatic ether, and an isoquinoline alkaloid.[1] It has been isolated from the Asian vine Menispermum dauricum, commonly known as Asian moonseed, and the North American vine Menispermum canadense, commonly known as Canadian moonseed.[2] Scientists Tetsuji Kametani and Keiichiro Fukumoto of Japan are credited with being the first to synthesize dauricine in 1964, using both the Arndt-Eistert reaction and Bischler-Napieralski reaction to do so.[3] Dauricine has been show to play a variety of biological roles in the human body, from inhibiting cancer cell growth[4][5][6][7] to blocking cardiac transmembrane Na+, K+, and Ca2+ ion currents.[8]

Dauricine and Cancer

Dauricine and Colon Cancer:

Dauricine has been shown to have anti-tumor effects in colon cancer.[9] There is evidence to suggest that dauricine suppresses colon cancer cell growth and invasion in a dose-dependent manner.[10] Dauricine has also been shown to induce apoptosis in colon cancer cells by facilitating the cleavage of caspase3 and poly ADP ribose polymerase (PARP).[11] Furthermore, it is thought that dauricine suppresses tumor necrosis factor-induced (TNF-induced) nuclear factor-kappa B (NF-κB) activation by inhibiting the p65 nuclear translocation in colon cancer cells.[12] Together, these discoveries help scientists better understand the link between dauricine and the suppression of colon cancer tumor cells.

Dauricine and Lung Cancer:

Dauricine has been shown to cause cytotoxicity in human lung cell lines, including BEAS-2B, WI-38, and A5449, which have been implicated in lung bronchus, lung fibroblast, and lung cancer, respectively.[13] One study found that after 24-hour exposure to 40 µM dauricine, there was more than 60% cell death in the aforementioned human lung cell lines.[14] Moreover, CYP3A, a class of human recombinant P450 enzymes, have been found to activate dauricine in human lung cells, resulting in the formation of quinone methide metabolite whose role in lung cytotoxicity needs to be further studied.[15] Overall, dauricine-induced cytotoxicity in human lung cells raises concerns about the use of dauricine and its analogues in pharmaceuticals.[16]

Dauricine and Breast Cancer:

Dauricine has been shown to inhibit human breast cancer angiogenesis.[17] Dauricine inhibits insulin-like growth factor-I-induced (IGF-I-induced) hypoxia-inducible factor I-alpha (HIF-Iα) protein accumulation and vascular endothelial growth factor (VEGF) protein secretion in MCF-7, human breast cancer cells.[18] It is thought that dauricine inhibits IGF-1-induced HIF-1α protein accumulation and VEGF protein secretion by blocking the activation of the PI-3K/AKT/mTOR signaling pathway.[19] Both HIF-1α and VEGF play an important role in human breast cancer angiogenesis.[20] Thus, dauricine’s inhibitory effect on these molecules is a promising point of study for human breast cancer treatment.[21]

Dauricine and Urinary Cancer:

Dauricine has been shown to have anti-tumor effects in various urinary cancers, including bladder cancer and prostate cancer.[22] It has been found that dauricine has a minimum drug sensitivity concentration between 3.81-5.15 µg/mL in bladder cancer EJ cells and prostate cancer PC-3M cells.[23] In addition, there is evidence to suggest that cytotoxicity in urinary cancer cells depends upon drug concentration.[24] The exact anti-tumor mechanism present in these urinary cancer cells has yet to be determined.[25]

References

  1. ↑ "CHEBI:4331 - dauricine". ChEBI. Retrieved 30 May 2015.
  2. ↑ Kametani, Tetsuji; Fukumoto, Keiichiro (1964). "Total synthesis of (±)-dauricine". Tetrahedron Letters. 5 (38): 2771–2775. doi:10.1016/S0040-4039(00)71728-X.
  3. ↑ Manske, R.H.F. (1967). The Alkaloids: Chemistry and Physiology V9. New York: Academic Press. p. 141. ISBN 9780080865331. Retrieved 30 May 2015.
  4. ↑ Yang, Zhengfeng; Li, Chenghai; Wang, Xiu; Zhai, Chunyan; Yi, Zhengfang; Wang, Lei; Liu, Bisheng; Du, Bing; Wu, Huihui; Guo, Xizhi; Liu, Mingyao; Li, Dali; Luo, Jian (2010). "Dauricine induces apoptosis, inhibits proliferation and invasion through inhibiting NF-kappaB signaling pathway in colon cancer cells". J. Cell. Physiol. 225 (1): 266–75. doi:10.1002/jcp.22261. PMID 20509140.
  5. ↑ Jin, Hua; Dai, Jieyu; Chen, Xiaoyan; Liu, Jia; Zhong, Dafang; Gu, Yansong; Zheng, Jiang (2009). "Pulmonary Toxicity and Metabolic Activation of Dauricine in CD-1 Mice". The Journal of Pharmacology and Experimental Therapeutics. 332 (3): 738–46. doi:10.1124/jpet.109.162297. Retrieved 30 May 2015.
  6. ↑ Tang, Xu-dong; Zhou, Xin; Zhou, Ke-yuan (2009). "Dauricine inhibits insulin-like growth factor-I-induced hypoxia inducible factor 1alpha protein accumulation and vascular endothelial growth factor expression in human breast cancer cells". Acta Pharmacol Sin. 30 (5): 605–16. doi:10.1038/aps.2009.8. PMC 4002832Freely accessible. PMID 19349962.
  7. ↑ Wang, Jun; Li, Yuan; Zu, Xiong-Bing; Chen, Min-Feng; Qi, Li (2012). "Dauricine can inhibit the activity of proliferation of urinary tract tumor cells". Asian Pac J Trop Med. 5 (12): 973–76. doi:10.1016/S1995-7645(12)60185-0. PMID 23199717.
  8. ↑ Qian, JQ (2002). "Cardiovascular pharmacological effects of bisbenzylisoquinoline alkaloid derivatives". Acta Pharmacol Sin. 23 (12): 1086–92. PMID 12466045.
  9. ↑ Yang, Zhengfeng; Li, Chenghai; Wang, Xiu; Zhai, Chunyan; Yi, Zhengfang; Wang, Lei; Liu, Bisheng; Du, Bing; Wu, Huihui; Guo, Xizhi; Liu, Mingyao; Li, Dali; Luo, Jian (2010). "Dauricine induces apoptosis, inhibits proliferation and invasion through inhibiting NF-kappaB signaling pathway in colon cancer cells". J. Cell. Physiol. 225 (1): 266–75. doi:10.1002/jcp.22261. PMID 20509140.
  10. ↑ Yang, Zhengfeng; Li, Chenghai; Wang, Xiu; Zhai, Chunyan; Yi, Zhengfang; Wang, Lei; Liu, Bisheng; Du, Bing; Wu, Huihui; Guo, Xizhi; Liu, Mingyao; Li, Dali; Luo, Jian (2010). "Dauricine induces apoptosis, inhibits proliferation and invasion through inhibiting NF-kappaB signaling pathway in colon cancer cells". J. Cell. Physiol. 225 (1): 266–75. doi:10.1002/jcp.22261. PMID 20509140.
  11. ↑ Yang, Zhengfeng; Li, Chenghai; Wang, Xiu; Zhai, Chunyan; Yi, Zhengfang; Wang, Lei; Liu, Bisheng; Du, Bing; Wu, Huihui; Guo, Xizhi; Liu, Mingyao; Li, Dali; Luo, Jian (2010). "Dauricine induces apoptosis, inhibits proliferation and invasion through inhibiting NF-kappaB signaling pathway in colon cancer cells". J. Cell. Physiol. 225 (1): 266–75. doi:10.1002/jcp.22261. PMID 20509140.
  12. ↑ Yang, Zhengfeng; Li, Chenghai; Wang, Xiu; Zhai, Chunyan; Yi, Zhengfang; Wang, Lei; Liu, Bisheng; Du, Bing; Wu, Huihui; Guo, Xizhi; Liu, Mingyao; Li, Dali; Luo, Jian (2010). "Dauricine induces apoptosis, inhibits proliferation and invasion through inhibiting NF-kappaB signaling pathway in colon cancer cells". J. Cell. Physiol. 225 (1): 266–75. doi:10.1002/jcp.22261. PMID 20509140.
  13. ↑ Jin, Hua; Dai, Jieyu; Chen, Xiaoyan; Liu, Jia; Zhong, Dafang; Gu, Yansong; Zheng, Jiang (2009). "Pulmonary Toxicity and Metabolic Activation of Dauricine in CD-1 Mice". The Journal of Pharmacology and Experimental Therapeutics. 332 (3): 738–46. doi:10.1124/jpet.109.162297. Retrieved 30 May 2015.
  14. ↑ Jin, Hua; Dai, Jieyu; Chen, Xiaoyan; Liu, Jia; Zhong, Dafang; Gu, Yansong; Zheng, Jiang (2009). "Pulmonary Toxicity and Metabolic Activation of Dauricine in CD-1 Mice". The Journal of Pharmacology and Experimental Therapeutics. 332 (3): 738–46. doi:10.1124/jpet.109.162297. Retrieved 30 May 2015.
  15. ↑ Jin, Hua; Dai, Jieyu; Chen, Xiaoyan; Liu, Jia; Zhong, Dafang; Gu, Yansong; Zheng, Jiang (2009). "Pulmonary Toxicity and Metabolic Activation of Dauricine in CD-1 Mice". The Journal of Pharmacology and Experimental Therapeutics. 332 (3): 738–46. doi:10.1124/jpet.109.162297. Retrieved 30 May 2015.
  16. ↑ Jin, Hua; Dai, Jieyu; Chen, Xiaoyan; Liu, Jia; Zhong, Dafang; Gu, Yansong; Zheng, Jiang (2009). "Pulmonary Toxicity and Metabolic Activation of Dauricine in CD-1 Mice". The Journal of Pharmacology and Experimental Therapeutics. 332 (3): 738–46. doi:10.1124/jpet.109.162297. Retrieved 30 May 2015.
  17. ↑ Tang, Xu-dong; Zhou, Xin; Zhou, Ke-yuan (2009). "Dauricine inhibits insulin-like growth factor-I-induced hypoxia inducible factor 1alpha protein accumulation and vascular endothelial growth factor expression in human breast cancer cells". Acta Pharmacol Sin. 30 (5): 605–16. doi:10.1038/aps.2009.8. PMC 4002832Freely accessible. PMID 19349962.
  18. ↑ Tang, Xu-dong; Zhou, Xin; Zhou, Ke-yuan (2009). "Dauricine inhibits insulin-like growth factor-I-induced hypoxia inducible factor 1alpha protein accumulation and vascular endothelial growth factor expression in human breast cancer cells". Acta Pharmacol Sin. 30 (5): 605–16. doi:10.1038/aps.2009.8. PMC 4002832Freely accessible. PMID 19349962.
  19. ↑ Tang, Xu-dong; Zhou, Xin; Zhou, Ke-yuan (2009). "Dauricine inhibits insulin-like growth factor-I-induced hypoxia inducible factor 1alpha protein accumulation and vascular endothelial growth factor expression in human breast cancer cells". Acta Pharmacol Sin. 30 (5): 605–16. doi:10.1038/aps.2009.8. PMC 4002832Freely accessible. PMID 19349962.
  20. ↑ Tang, Xu-dong; Zhou, Xin; Zhou, Ke-yuan (2009). "Dauricine inhibits insulin-like growth factor-I-induced hypoxia inducible factor 1alpha protein accumulation and vascular endothelial growth factor expression in human breast cancer cells". Acta Pharmacol Sin. 30 (5): 605–16. doi:10.1038/aps.2009.8. PMC 4002832Freely accessible. PMID 19349962.
  21. ↑ Tang, Xu-dong; Zhou, Xin; Zhou, Ke-yuan (2009). "Dauricine inhibits insulin-like growth factor-I-induced hypoxia inducible factor 1alpha protein accumulation and vascular endothelial growth factor expression in human breast cancer cells". Acta Pharmacol Sin. 30 (5): 605–16. doi:10.1038/aps.2009.8. PMC 4002832Freely accessible. PMID 19349962.
  22. ↑ Wang, Jun; Li, Yuan; Zu, Xiong-Bing; Chen, Min-Feng; Qi, Li (2012). "Dauricine can inhibit the activity of proliferation of urinary tract tumor cells". Asian Pac J Trop Med. 5 (12): 973–76. doi:10.1016/S1995-7645(12)60185-0. PMID 23199717.
  23. ↑ Wang, Jun; Li, Yuan; Zu, Xiong-Bing; Chen, Min-Feng; Qi, Li (2012). "Dauricine can inhibit the activity of proliferation of urinary tract tumor cells". Asian Pac J Trop Med. 5 (12): 973–76. doi:10.1016/S1995-7645(12)60185-0. PMID 23199717.
  24. ↑ Wang, Jun; Li, Yuan; Zu, Xiong-Bing; Chen, Min-Feng; Qi, Li (2012). "Dauricine can inhibit the activity of proliferation of urinary tract tumor cells". Asian Pac J Trop Med. 5 (12): 973–76. doi:10.1016/S1995-7645(12)60185-0. PMID 23199717.
  25. ↑ Wang, Jun; Li, Yuan; Zu, Xiong-Bing; Chen, Min-Feng; Qi, Li (2012). "Dauricine can inhibit the activity of proliferation of urinary tract tumor cells". Asian Pac J Trop Med. 5 (12): 973–76. doi:10.1016/S1995-7645(12)60185-0. PMID 23199717.
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