Plicamycin
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| Systematic (IUPAC) name | |
|---|---|
|
(1S)-5-deoxy-1-C-((2S,3S)-7-{[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl]oxy}-3-{[2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy}-5,10-dihydroxy-6-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-2-yl)-1-O-methyl-D-xylulose | |
| Clinical data | |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| Pregnancy category |
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| Legal status |
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| Routes of administration | Intravenous |
| Identifiers | |
| CAS Number |
18378-89-7  |
| ATC code | L01DC02 |
| PubChem | CID 5284610 |
| DrugBank |
DB06810 |
| ChemSpider |
4447655 |
| UNII |
NIJ123W41V |
| KEGG |
D00468  |
| ChEMBL |
CHEMBL509846 |
| Synonyms | Aureolic acid; Mithracin; Antibiotic LA 7017; Mithramycin A; Mitramycin; Plicatomycin |
| Chemical data | |
| Formula | C52H76O24 |
| Molar mass | 1085.15 g/mol |
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| (what is this?) (verify) | |
Plicamycin (INN, also known as mithramycin; trade name Mithracin) is an antineoplastic antibiotic produced by Streptomyces plicatus. It is an RNA synthesis inhibitor.[1] The manufacturer discontinued production in 2000. Several different structures are currently reported in different places all with the same chromomycin core, but with different stereochemistry in the glycoside chain, a 1999 study has re-investigated the compound and proposed a revised structure. [2]
Uses
Plicamycin has been used in the treatment of testicular cancer,[3][4] Paget's disease of bone,[5][6] and, rarely, the management of hypercalcemia.
Plicamycin has been tested in chronic myeloid leukemia.[7]
Plicamycin is currently used in multiple areas of research, including cancer cell apoptosis[8] and as a metastasis inhibitor.[9]
One elucidated pathway shows it interacts by cross-binding chromatin GC-rich promoter motifs, thereby inhibiting gene transcription.[10]
References
- ↑ "Mithramycin A". Fermentek.
- ↑ Wohlert, S. E.; Künzel, E.; Machinek, R.; Méndez, C.; Salas, J. A.; Rohr, J. "The Structure of Mithramycin Reinvestigated". Journal of Natural Products 62 (1): 119–121. doi:10.1021/np980355k.
- ↑ Kennedy BJ, Torkelson JL (May 1995). "Long-term follow-up of stage III testicular carcinoma treated with mithramycin (plicamycin)". Med. Pediatr. Oncol. 24 (5): 327–8. doi:10.1002/mpo.2950240511. PMID 7700186.
- ↑ Brown, John H.; Kennedy, B. J. (1965). "Mithramycin in the Treatment of Disseminated Testicular Neoplasms". New England Journal of Medicine 272 (3): 111–8. doi:10.1056/NEJM196501212720301. PMID 14224214.
- ↑ Hall, T; Schaeublin, M; Chambers, TJ (1993). "The Majority of Osteoclasts Require mRNA and Protein Synthesis for Bone Resorption in Vitro". Biochemical and Biophysical Research Communications 195 (3): 1245–53. doi:10.1006/bbrc.1993.2178. PMID 8216256.
- ↑ Remsing, Lily L.; Bahadori, Hamid R.; Carbone, Giuseppina M.; McGuffie, Eileen M.; Catapano, Carlo V.; Rohr, Jürgen (2003). "Inhibition of c-src Transcription by Mithramycin: Structure−Activity Relationships of Biosynthetically Produced Mithramycin Analogues Using the c-src Promoter as Target". Biochemistry 42 (27): 8313–24. doi:10.1021/bi034091z. PMID 12846580.
- ↑ Dutcher JP, Coletti D, Paietta E, Wiernik PH (May 1997). "A pilot study of alpha-interferon and plicamycin for accelerated phase of chronic myeloid leukemia". Leuk. Res. 21 (5): 375–80. doi:10.1016/S0145-2126(96)00108-7. PMID 9225062.
- ↑ Lee, Tae-Jin; Jung, Eun Mi; Lee, Jung Tae; Kim, Shin; Park, Jong-Wook; Choi, Kyeong Sook; Kwon, Taeg Kyu (2006). "Mithramycin a sensitizes cancer cells to TRAIL-mediated apoptosis by down-regulation of XIAP gene promoter through Sp1 sites". Molecular Cancer Therapeutics 5 (11): 2737–46. doi:10.1158/1535-7163.MCT-06-0426. PMID 17121920.
- ↑ Lin, Ruo-Kai; Hsu, Chun-Hua; Wang, Yi-Ching (2007). "Mithramycin a inhibits DNA methyltransferase and metastasis potential of lung cancer cells". Anti-Cancer Drugs 18 (10): 1157–64. doi:10.1097/CAD.0b013e3282a215e9. PMID 17893516.
- ↑ Majee, Sangita; Chakrabarti, Abhijit (1999). "Membrane interaction of an antitumor antibiotic, mithramycin, with anionic phospholipid vesicles". Biochemical Pharmacology 57 (9): 981–7. doi:10.1016/S0006-2952(98)00374-8. PMID 10796068.
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