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Plicamycin - ≥95%, high purity , CAS No.18378-89-7

2 Citations
Item Number
P113149
Grouped product items
SKUSizeAvailabilityPrice Qty
P113149-1mg
1mg
In stock
$167.90
P113149-5mg
5mg
In stock
$513.90
P113149-25mg
25mg
In stock
$1,761.90
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DNA and RNA polymerase inhibitor. DNA binding transciptional inhibitor.

Basic Description

SynonymsMithramycin A | Aurlelic acid | DB06810 | PA-144 | MITHRAMYCINA | MITHRAMYCIN | BDBM50547623 | Plicamycin [USAN:USP:INN:BAN] | PLICAMYCIN [USAN] | D00468 | Antibiotic LA 7017 | Mithramycinum | Mitramycine | plicamycin | Aureolic acid | CCRIS 5629 | NJWSNN
Specifications & PurityMoligand™, ≥95%
Biochemical and Physiological MechanismsAnticancer antibiotic. Inhibits transcription and protein synthesis. Binds to DNA in native chromatin. Substrate of Pgp in MDR phenotypes.DNA and RNA polymerase inhibitor, DNA binding transcriptional inhibitor (Sp1 and Sp3). Shows antineoplastic activity.
Storage TempStore at -20°C,Argon charged
Shipped InIce chest + Ice pads
GradeMoligand™
NoteWherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
Product Description

Mithramycin A is an antibiotic DNA/RNA polymerase and DNA binding transcriptional inhibitor observed to facilitate TNF-α and Fas-ligand induced apoptosis. As a DNA binding transcriptional inhibitor, mithramycin A binds to GC rich sequences located in the minor groove of DNA and is noted to be reversible and Mg2+ dependent. Additionally reported to a block transcriptional activation of the SV40 promoter via competitive binding against Sp1 transcription factor to GC rich areas in the early promoter. Mithramycin A is noted to supress TNF-α induced expression of fractalkine (CX3CL1) mRNA in a dose-dependent manner and to act as an effective differentiation agent of HL60 promyelocytic leukemia cells
A polymerase inhibitor that binds to GC rich sequences located in the minor groove of DNA;DNA binding fluorescent dye. Until 2000 it was used to reduce high levels of plasma calcium; Used as an antineoplastic agent

Associated Targets(Human)

A673 (619 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PANC-1 (6144 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Prostatic carcinoma cell (85 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LNCaP (8286 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DMS-114 (15429 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-118-MG (352 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ES8 (149 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ES7 (149 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EWSR1 Tbio Friend leukemia integration 1 transcription factor (Proto-oncogene Fli-1)/RNA-binding protein EWS (19 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TC-32 (111 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
VCaP (1078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Names and Identifiers

IUPAC Name (2S,3S)-2-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4-[(2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-6-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-8,9-dihydroxy-7-methyl-3,4-dihydro-2H-anthracen-1-one
INCHI 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
InChi Key CFCUWKMKBJTWLW-BKHRDMLASA-N
Canonical SMILES CC1C(C(CC(O1)OC2CC(OC(C2O)C)OC3=CC4=CC5=C(C(=O)C(C(C5)C(C(=O)C(C(C)O)O)OC)OC6CC(C(C(O6)C)O)OC7CC(C(C(O7)C)O)OC8CC(C(C(O8)C)O)(C)O)C(=C4C(=C3C)O)O)O)O
Isomeric SMILES C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2C[C@@H](O[C@@H]([C@H]2O)C)OC3=CC4=CC5=C(C(=O)[C@H]([C@@H](C5)[C@@H](C(=O)[C@H]([C@@H](C)O)O)OC)O[C@H]6C[C@H]([C@@H]([C@H](O6)C)O)O[C@H]7C[C@H]([C@H]([C@H](O7)C)O)O[C@H]8C[C@]([C@@H]([C@H](O8)C)O)(C)O)C(=C4C(=C3C)O)O)O)O
WGK Germany 3
RTECS PZ2800000
PubChem CID 163659
UN Number 2811
Molecular Weight 1085.15
Beilstein 5236667

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

Find and download the COA for your product by matching the lot number on the packaging.

6 results found

Lot NumberCertificate TypeDateItem
I2419126Certificate of AnalysisSep 28, 2024 P113149
E2225243Certificate of AnalysisFeb 23, 2024 P113149
E2225244Certificate of AnalysisFeb 23, 2024 P113149
E2225253Certificate of AnalysisFeb 23, 2024 P113149
L2109072Certificate of AnalysisSep 21, 2023 P113149
L2109073Certificate of AnalysisSep 21, 2023 P113149

Chemical and Physical Properties

SolubilitySoluble in phosphate buffered saline (1 mg/ml), ethanol, ethyl acetate, lower alcohols, and acetone. Insoluble in water.
Sensitivitylight sensitive & Moisture sensitive
Melt Point(°C)170-175°C

Safety and Hazards(GHS)

Pictogram(s) GHS07
Signal Warning
Hazard Statements

H302:Harmful if swallowed

Precautionary Statements

P501:Dispose of contents/container to ...

P264:Wash hands [and …] thoroughly after handling.

P270:Do not eat, drink or smoke when using this product.

P330:Rinse mouth.

P301+P317:IF SWALLOWED: Get medical help.

WGK Germany 3
RTECS PZ2800000

Related Documents

 SDS

 Specification Sheet

Citations of This Product

How to Cite Aladdin Scientific Products?
1. Danfeng Wang, Min Liu, Yushu Wu, Tianxin Weng, Lu Wang, Yongfang Zhang, Yanna Zhao, Jun Han.  (2022)  Idarubicin/mithramycin-acridine orange combination drugs co-loaded by DNA nanostructures: Different effects of intercalation and groove binding on drug release and cytotoxicity.  JOURNAL OF MOLECULAR LIQUIDS,  355  (118947).  [PMID:] [10.1016/j.molliq.2022.118947]
2. Danfeng Wang, Min Liu, Yushu Wu, Yanna Zhao, Qingpeng Wang, Tianxin Weng, Lu Wang, He Liu, Yongfang Ren, Jun Han.  (2021)  Self-assembled DNA nanotrains for targeted delivery of mithramycin dimers coordinated by different metal ions: Effect of binding affinity on drug loading, release and cytotoxicity.  JOURNAL OF MOLECULAR LIQUIDS,  339  (116722).  [PMID:] [10.1016/j.molliq.2021.116722]

References

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17. Wei-feng Zhao,Hong-bo Wang,Bo Xie,Li-juan Hu,Li-hua Xu,Bo-hua Kuang,Man-zhi Li,Xing Zhang.  (2012-06-12)  Sp1 and Sp3 are involved in the full transcriptional activity of centromere protein H in human nasopharyngeal carcinoma cells..  The FEBS journal,  279  ((15)): (2714-2726).  [PMID:22682030]
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19. Jiansheng Lu,Yihua Ma,Jianjia Liang,Yingying Xing,Tao Xi,Yuanyuan Lu.  (2012-07-14)  Aureolic acids from a marine-derived Streptomyces sp. WBF16..  Microbiological research,  167  ((10)): (590-595).  [PMID:22789867]
20. G Gopisetty,J Xu,D Sampath,H Colman,V K Puduvalli.  (2012-09-05)  Epigenetic regulation of CD133/PROM1 expression in glioma stem cells by Sp1/myc and promoter methylation..  Oncogene,  32  ((26)): (3119-3129).  [PMID:22945648]
21. Tsung-I Hsu,Mei-Chun Wang,Szu-Yu Chen,Shih-Ting Huang,Yu-Min Yeh,Wu-Chou Su,Wen-Chang Chang,Jan-Jong Hung.  (2012-09-08)  Betulinic acid decreases specificity protein 1 (Sp1) level via increasing the sumoylation of sp1 to inhibit lung cancer growth..  Molecular pharmacology,  82  ((6)): (1115-1128).  [PMID:22956772]
22. Carolina Vizcaíno,Sylvia Mansilla,Luz-Elena Núñez,Carmen Méndez,José A Salas,Francisco Morís,José Portugal.  (2012-09-18)  Novel mithramycins abrogate the involvement of protein factors in the transcription of cell cycle control genes..  Biochemical pharmacology,  84  ((9)): (1133-1142).  [PMID:22981341]
23. Guojun Wang,Pallab Pahari,Madan K Kharel,Jing Chen,Haining Zhu,Steven G Van Lanen,Jürgen Rohr.  (2012-09-22)  Cooperation of two bifunctional enzymes in the biosynthesis and attachment of deoxysugars of the antitumor antibiotic mithramycin..  Angewandte Chemie (International ed. in English),  51  ((42)): (10638-10642).  [PMID:22997042]
24. S Min,L Li,M Zhang,Y Zhang,X Liang,Y Xie,Q He,Y Li,J Sun,Q Liu,X Jiang,Y Zhang,Y Che,R Yang.  (2012-10-05)  TGF-β-associated miR-27a inhibits dendritic cell-mediated differentiation of Th1 and Th17 cells by TAB3, p38 MAPK, MAP2K4 and MAP2K7..  Genes and immunity,  13  ((8)): (621-631).  [PMID:23034448]
25. Chun-Wei Hsu,Chia-Feng Kuo,Show-Mei Chuang,Ming-Hon Hou.  (2012-10-26)  Elucidation of the DNA-interacting properties and anticancer activity of a Ni(II)-coordinated mithramycin dimer complex..  Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine,  26  ((1)): (1-12).  [PMID:23097078]
26. Marina Isshiki,Haruka Ohta,Hiroomi Tamura.  (2013-02-02)  Coffee reduces SULT1E1 expression in human colon carcinoma Caco-2 cells..  Biological & pharmaceutical bulletin,  36  ((2)): (299-304).  [PMID:23370358]
27. M Jin,A Ande,A Kumar,S Kumar.  (2013-03-23)  Regulation of cytochrome P450 2e1 expression by ethanol: role of oxidative stress-mediated pkc/jnk/sp1 pathway..  Cell death & disease,  4  (e554-e554).  [PMID:23519123]
28. Bhavana Chhunchha,Eri Kubo,Prerna Singh,Dhirendra P Singh.  (2018-09-15)  Sumoylation-deficient Prdx6 repairs aberrant Sumoylation-mediated Sp1 dysregulation-dependent Prdx6 repression and cell injury in aging and oxidative stress..  Aging,  10  ((9)): (2284-2315).  [PMID:30215601]
29. Valentina Sica,Jose Manuel Bravo-San Pedro,Valentina Izzo,Jonathan Pol,Sandra Pierredon,David Enot,Sylvère Durand,Noélie Bossut,Alexis Chery,Sylvie Souquere,Gerard Pierron,Evangelia Vartholomaiou,Naoufal Zamzami,Thierry Soussi,Allan Sauvat,Laura Mondragón,Oliver Kepp,Lorenzo Galluzzi,Jean-Claude Martinou,Holger Hess-Stumpp,Karl Ziegelbauer,Guido Kroemer,Maria Chiara Maiuri.  (2019-04-18)  Lethal Poisoning of Cancer Cells by Respiratory Chain Inhibition plus Dimethyl α-Ketoglutarate..  Cell reports,  27  ((3)): (820-834).  [PMID:30995479]
30. Han Cai,Bingying Liu,Huarong Wang,Guanghong Sun,Lizhao Feng,Ziqi Chen,Jiaqi Zhou,Jiawei Zhang,Tuo Zhang,Meina He,Tingting Yang,Qirui Guo,Zhen Teng,Qiliang Xin,Bo Zhou,Hua Zhang,Guoliang Xia,Chao Wang.  (2019-07-10)  SP1 governs primordial folliculogenesis by regulating pregranulosa cell development in mice..  Journal of molecular cell biology,  12  ((3)): (230-244).  [PMID:31282930]
31. Waise Quarni,Rinku Dutta,Ryan Green,Sandhyabanu Katiri,Bhaumik Patel,Shyam S Mohapatra,Subhra Mohapatra.  (2019-10-28)  Mithramycin A Inhibits Colorectal Cancer Growth by Targeting Cancer Stem Cells..  Scientific reports,  9  ((1)): (15202-15202).  [PMID:31645574]
32. Yang Zhou,Yunjiang Zhou,Keke Wang,Tao Li,Minda Zhang,Yunjia Yang,Rui Wang,Rong Hu.  (2019-12-01)  ROCK2 Confers Acquired Gemcitabine Resistance in Pancreatic Cancer Cells by Upregulating Transcription Factor ZEB1..  Cancers,  11  ((12)):   [PMID:31783584]
33. Ushasree Mrudulakumari Vasudevan,Eun Yeol Lee.  (2020-05-04)  Flavonoids, terpenoids, and polyketide antibiotics: Role of glycosylation and biocatalytic tactics in engineering glycosylation..  Biotechnology advances,  41  (107550-107550).  [PMID:32360984]
34. Takashi Furuta,Tsuyoshi Shuto,Shogo Shimasaki,Yuko Ohira,Mary Ann Suico,Dieter C Gruenert,Hirofumi Kai.  (2008-04-22)  DNA demethylation-dependent enhancement of toll-like receptor-2 gene expression in cystic fibrosis epithelial cells involves SP1-activated transcription..  BMC molecular biology,  9  (39-39).  [PMID:18423053]
35. Wangsheng Wang,Jianneng Li,Yuchun Ge,Wenjiao Li,Qun Shu,Haiyan Guan,Kaiping Yang,Leslie Myatt,Kang Sun.  (2012-02-09)  Cortisol induces aromatase expression in human placental syncytiotrophoblasts through the cAMP/Sp1 pathway..  Endocrinology,  153  ((4)): (2012-2022).  [PMID:22315456]
36. Anastasia Malek,Luz-Elena Núñez,Marco Magistri,Lara Brambilla,Sandra Jovic,Giuseppina M Carbone,Francisco Morís,Carlo V Catapano.  (2012-05-01)  Modulation of the activity of Sp transcription factors by mithramycin analogues as a new strategy for treatment of metastatic prostate cancer..  PloS one,  7  ((4)): (e35130-e35130).  [PMID:22545098]
37. Y Peter Di,Jinming Zhao,Richart Harper.  (2012-06-16)  Cigarette smoke induces MUC5AC protein expression through the activation of Sp1..  The Journal of biological chemistry,  287  ((33)): (27948-27958).  [PMID:22700966]
38. Paula C M Sales,Bryan R G Williams,Aristóbolo M Silva.  (2012-08-10)  Regulation of double-stranded RNA dependent protein kinase expression and attenuation of protein synthesis induced by bacterial toll-like receptors agonists in the absence of interferon..  Journal of interferon & cytokine research : the official journal of the International Society for Interferon and Cytokine Research,  32  ((10)): (495-504).  [PMID:22873641]
39. Eun-Sun Choi,Ji-Youn Jung,Jin-Seok Lee,Jong-Hwan Park,Nam-Pyo Cho,Sung-Dae Cho.  (2012-09-25)  Myeloid cell leukemia-1 is a key molecular target for mithramycin A-induced apoptosis in androgen-independent prostate cancer cells and a tumor xenograft animal model..  Cancer letters,  328  ((1)): (65-72).  [PMID:23000424]
40. Ji-Ae Shin,Ji-Youn Jung,Mi Heon Ryu,Stephen Safe,Sung-Dae Cho.  (2012-09-29)  Mithramycin A inhibits myeloid cell leukemia-1 to induce apoptosis in oral squamous cell carcinomas and tumor xenograft through activation of Bax and oligomerization..  Molecular pharmacology,  83  ((1)): (33-41).  [PMID:23019217]
41. Pham Thi Thu Huong,Nak Kyun Soung,Jae Hyuk Jang,Hyun Joo Cha-Molstad,Krisada Sakchaisri,Sun Ok Kim,Jun Min Jang,Kyoon Eon Kim,Kyung Sang Lee,Yong Tae Kwon,Raymond Leo Erikson,Jong Seog Ahn,Bo Yeon Kim.  (2012-11-10)  Regulation of CEP131 gene expression by SP1..  Gene,  513  ((1)): (75-81).  [PMID:23137637]
42. Alexa Klettner,Daniel Westhues,Jens Lassen,Sofia Bartsch,Johann Roider.  (2013-02-13)  Regulation of constitutive vascular endothelial growth factor secretion in retinal pigment epithelium/choroid organ cultures: p38, nuclear factor κB, and the vascular endothelial growth factor receptor-2/phosphatidylinositol 3 kinase pathway..  Molecular vision,  19  (281-291).  [PMID:23401656]
43. Robert J Vanner,Marc Remke,Marco Gallo,Hayden J Selvadurai,Fiona Coutinho,Lilian Lee,Michelle Kushida,Renee Head,Sorana Morrissy,Xueming Zhu,Tzvi Aviv,Veronique Voisin,Ian D Clarke,Yisu Li,Andrew J Mungall,Richard A Moore,Yussanne Ma,Steven J M Jones,Marco A Marra,David Malkin,Paul A Northcott,Marcel Kool,Stefan M Pfister,Gary Bader,Konrad Hochedlinger,Andrey Korshunov,Michael D Taylor,Peter B Dirks.  (2014-06-24)  Quiescent sox2(+) cells drive hierarchical growth and relapse in sonic hedgehog subgroup medulloblastoma..  Cancer cell,  26  ((1)): (33-47).  [PMID:24954133]
44. Keizo Takenaga,Takahiro Ochiya,Hideya Endo.  (2021-03-03)  Inhibition of the invasion and metastasis of mammary carcinoma cells by NBD peptide targeting S100A4 via the suppression of the Sp1/MMP‑14 axis..  International journal of oncology,  58  ((3)): (397-408).  [PMID:33650647]
45. Annapaola Angrisani,Annamaria Di Fiore,Claudia Augusta Di Trani,Simone Fonte,Marialaura Petroni,Ludovica Lospinoso Severini,Fabio Bordin,Laura Belloni,Elisabetta Ferretti,Gianluca Canettieri,Marta Moretti,Enrico De Smaele.  (2021-04-27)  Specific Protein 1 and p53 Interplay Modulates the Expression of the KCTD-Containing Cullin3 Adaptor Suppressor of Hedgehog 2..  Frontiers in cell and developmental biology,  9  (638508-638508).  [PMID:33898425]
46. Danfeng Wang, Min Liu, Yushu Wu, Tianxin Weng, Lu Wang, Yongfang Zhang, Yanna Zhao, Jun Han.  (2022)  Idarubicin/mithramycin-acridine orange combination drugs co-loaded by DNA nanostructures: Different effects of intercalation and groove binding on drug release and cytotoxicity.  JOURNAL OF MOLECULAR LIQUIDS,  355  (118947).  [PMID:] [10.1016/j.molliq.2022.118947]
47. Danfeng Wang, Min Liu, Yushu Wu, Yanna Zhao, Qingpeng Wang, Tianxin Weng, Lu Wang, He Liu, Yongfang Ren, Jun Han.  (2021)  Self-assembled DNA nanotrains for targeted delivery of mithramycin dimers coordinated by different metal ions: Effect of binding affinity on drug loading, release and cytotoxicity.  JOURNAL OF MOLECULAR LIQUIDS,  339  (116722).  [PMID:] [10.1016/j.molliq.2021.116722]

Solution Calculators

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