Plicamycin: Difference between revisions

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| verifiedrevid = 400856269
| verifiedrevid = 400856269
| IUPAC_name = (1''S'')-5-deoxy-1-''C''-((2''S'',3''S'')-7-{[2,6-dideoxy-3-''O''-(2,6-dideoxy-β-<small>D</small>-''arabino''-hexopyranosyl)-β-<small>D</small>-''arabino''-hexopyranosyl]oxy}-3-{[2,6-dideoxy-3-''C''-methyl-β-<small>D</small>-''ribo''-hexopyranosyl-(1&rarr;3)-2,6-dideoxy-β-<small>D</small>-''arabino''-hexopyranosyl-(1&rarr;3)-2,6-dideoxy-β-<small>D</small>-''arabino''-hexopyranosyl]oxy}-5,10-dihydroxy-6-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-2-yl)-1-''O''-methyl-<small>D</small>-xylulose
| IUPAC_name = (1''S'')-5-deoxy-1-''C''-((2''S'',3''S'')-7-{[2,6-dideoxy-3-''O''-(2,6-dideoxy-β-<small>D</small>-''arabino''-hexopyranosyl)-β-<small>D</small>-''arabino''-hexopyranosyl]oxy}-3-{[2,6-dideoxy-3-''C''-methyl-β-<small>D</small>-''ribo''-hexopyranosyl-(1&rarr;3)-2,6-dideoxy-β-<small>D</small>-''arabino''-hexopyranosyl-(1&rarr;3)-2,6-dideoxy-β-<small>D</small>-''arabino''-hexopyranosyl]oxy}-5,10-dihydroxy-6-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-2-yl)-1-''O''-methyl-<small>D</small>-xylulose
| synonyms = Aureolic acid; Mithracin; Antibiotic LA 7017; Mithramycin A; Mitramycin; Plicatomycin
| image = Plicamycin.svg
| image = Plicamycin.svg
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| routes_of_administration = [[Intravenous therapy|Intravenous]]
| routes_of_administration = [[Intravenous therapy|Intravenous]]
}}
}}

'''Plicamycin''' ([[International Nonproprietary Name|INN]], also known as '''mithramycin'''; trade name '''Mithracin''') is an [[antineoplastic]] [[antibiotic]] produced by ''[[Streptomyces|Streptomyces plicatus]]''.
'''Plicamycin''' ([[International Nonproprietary Name|INN]], also known as '''mithramycin'''; trade name '''Mithracin''') is an [[antineoplastic]] [[antibiotic]] produced by ''[[Streptomyces|Streptomyces plicatus]]''. It is an RNA synthesis inhibitor.<ref>{{cite web |url=http://www.fermentek.co.il/mithramycin_A.htm |title=Mithramycin A |publisher=[[Fermentek]]}}</ref>


==Uses==
==Uses==
It has been used in the treatment of [[testicular cancer]],<ref name="pmid7700186">{{cite journal |author=Kennedy BJ, Torkelson JL |title=Long-term follow-up of stage III testicular carcinoma treated with mithramycin (plicamycin) |journal=Med. Pediatr. Oncol. |volume=24 |issue=5 |pages=327–8 |year=1995 |month=May |pmid=7700186 |doi= 10.1002/mpo.2950240511|url=}}</ref> [[Paget's disease of bone]], and, rarely, the management of [[hypercalcemia]].
Plicamycin has been used in the treatment of [[testicular cancer]],<ref name="pmid7700186">{{cite journal |author=Kennedy BJ, Torkelson JL |title=Long-term follow-up of stage III testicular carcinoma treated with mithramycin (plicamycin) |journal=Med. Pediatr. Oncol. |volume=24 |issue=5 |pages=327–8 |year=1995 |month=May |pmid=7700186 |doi= 10.1002/mpo.2950240511|url=}}</ref><ref>{{cite journal |last1=Brown |first1=John H. |last2=Kennedy |first2=B. J. |title=Mithramycin in the Treatment of Disseminated Testicular Neoplasms |journal=New England Journal of Medicine |volume=272 |pages=111–8 |year=1965 |pmid=14224214 |doi=10.1056/NEJM196501212720301}}</ref> [[Paget's disease of bone]],<ref>{{cite journal |last1=Hall |first1=T |last2=Schaeublin |first2=M |last3=Chambers |first3=TJ |title=The Majority of Osteoclasts Require mRNA and Protein Synthesis for Bone Resorption in Vitro |journal=Biochemical and Biophysical Research Communications |volume=195 |issue=3 |pages=1245–53 |year=1993 |pmid=8216256 |doi=10.1006/bbrc.1993.2178}}</ref><ref>{{cite journal |last1=Remsing |first1=Lily L. |last2=Bahadori |first2=Hamid R. |last3=Carbone |first3=Giuseppina M. |last4=McGuffie |first4=Eileen M. |last5=Catapano |first5=Carlo V. |last6=Rohr |first6=Jürgen |title=Inhibition of ''c-src'' Transcription by Mithramycin: Structure−Activity Relationships of Biosynthetically Produced Mithramycin Analogues Using the ''c-src'' Promoter as Target |journal=Biochemistry |volume=42 |issue=27 |pages=8313–24 |year=2003 |pmid=12846580 |doi=10.1021/bi034091z}}</ref> and, rarely, the management of [[hypercalcemia]].


It has been tested in [[chronic myeloid leukemia]].<ref name="pmid9225062">{{cite journal |author=Dutcher JP, Coletti D, Paietta E, Wiernik PH |title=A pilot study of alpha-interferon and plicamycin for accelerated phase of chronic myeloid leukemia |journal=Leuk. Res. |volume=21 |issue=5 |pages=375–80 |year=1997 |month=May |pmid=9225062 |doi= 10.1016/S0145-2126(96)00108-7|url=http://linkinghub.elsevier.com/retrieve/pii/S0145212696001087}}</ref>
Plicamycin has been tested in [[chronic myeloid leukemia]].<ref name="pmid9225062">{{cite journal |author=Dutcher JP, Coletti D, Paietta E, Wiernik PH |title=A pilot study of alpha-interferon and plicamycin for accelerated phase of chronic myeloid leukemia |journal=Leuk. Res. |volume=21 |issue=5 |pages=375–80 |year=1997 |month=May |pmid=9225062 |doi= 10.1016/S0145-2126(96)00108-7|url=http://linkinghub.elsevier.com/retrieve/pii/S0145212696001087}}</ref>

Plicamycin is currently used in multiple areas of research, including cancer cell apoptosis<ref>{{cite journal |last1=Lee |first1=Tae-Jin |last2=Jung |first2=Eun Mi |last3=Lee |first3=Jung Tae |last4=Kim |first4=Shin |last5=Park |first5=Jong-Wook |last6=Choi |first6=Kyeong Sook |last7=Kwon |first7=Taeg Kyu |title=Mithramycin a sensitizes cancer cells to TRAIL-mediated apoptosis by down-regulation of XIAP gene promoter through Sp1 sites |journal=Molecular Cancer Therapeutics |volume=5 |issue=11 |pages=2737 |year=2006 |pmid=17121920 |doi=10.1158/1535-7163.MCT-06-0426}}</ref> and as a metastasis inhibitor.<ref>{{cite journal |last1=Lin |first1=Ruo-Kai |last2=Hsu |first2=Chun-Hua |last3=Wang |first3=Yi-Ching |title=Mithramycin a inhibits DNA methyltransferase and metastasis potential of lung cancer cells |journal=Anti-Cancer Drugs |volume=18 |issue=10 |pages=1157–64 |year=2007 |pmid=17893516 |doi=10.1097/CAD.0b013e3282a215e9}}</ref>

One elucidated pathway shows it interacts by cross-binding [[chromatin]] GC-rich promoter motifs, thereby inhibiting [[gene transcription]].<ref>{{cite journal |last1=Majee |first1=Sangita |last2=Chakrabarti |first2=Abhijit |title=Membrane interaction of an antitumor antibiotic, mithramycin, with anionic phospholipid vesicles |journal=Biochemical Pharmacology |volume=57 |issue=9 |pages=981–7 |year=1999 |pmid=10796068 |doi=10.1016/S0006-2952(98)00374-8}}</ref>


==References==
==References==
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{{Chemotherapeutic agents}}
{{Chemotherapeutic agents}}



[[Category:Antineoplastic drugs]]
[[Category:Antineoplastic drugs]]

Revision as of 18:42, 21 March 2011

Plicamycin
Clinical data
Other namesAureolic acid; Mithracin; Antibiotic LA 7017; Mithramycin A; Mitramycin; Plicatomycin
Routes of
administration		Intravenous
ATC code
Identifiers
  • (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
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.162.065 Edit this at Wikidata
Chemical and physical data
FormulaC52H76O24
Molar mass1085.15 g/mol g·mol−1
  • InChI=1S/C52H76O24/c1-18-29(72-34-14-30(43(58)21(4)68-34)73-33-13-28(54)42(57)20(3)67-33)12-26-10-25-11-27(49(66-9)48(63)41(56)19(2)53)50(47(62)39(25)46(61)38(26)40(18)55)76-36-16-31(44(59)23(6)70-36)74-35-15-32(45(60)22(5)69-35)75-37-17-52(8,65)51(64)24(7)71-37/h10,12,19-24,27-28,30-37,41-45,49-51,53-61,64-65H,11,13-17H2,1-9H3/t19-,20-,21-,22-,23-,24-,27?,28-,30-,31-,32-,33+,34+,35+,36+,37+,41+,42-,43+,44-,45-,49+,50+,51-,52+/m1/s1 checkY
  • Key:CFCUWKMKBJTWLW-GWRQQDNDSA-N checkY
  (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]

Uses

Plicamycin has been used in the treatment of testicular cancer,[2][3] Paget's disease of bone,[4][5] and, rarely, the management of hypercalcemia.

Plicamycin has been tested in chronic myeloid leukemia.[6]

Plicamycin is currently used in multiple areas of research, including cancer cell apoptosis[7] and as a metastasis inhibitor.[8]

One elucidated pathway shows it interacts by cross-binding chromatin GC-rich promoter motifs, thereby inhibiting gene transcription.[9]

References

  1. ^ "Mithramycin A". Fermentek.
  2. ^ Kennedy BJ, Torkelson JL (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. {{cite journal}}: Unknown parameter |month= ignored (help)
  3. ^ Brown, John H.; Kennedy, B. J. (1965). "Mithramycin in the Treatment of Disseminated Testicular Neoplasms". New England Journal of Medicine. 272: 111–8. doi:10.1056/NEJM196501212720301. PMID 14224214.
  4. ^ 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.
  5. ^ 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.
  6. ^ Dutcher JP, Coletti D, Paietta E, Wiernik PH (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  7. ^ 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. doi:10.1158/1535-7163.MCT-06-0426. PMID 17121920.
  8. ^ 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.
  9. ^ 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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