Basic Description

Synonyms	MITHRAMYCIN \| plicamycin \| Mithracin \| mithramycin a \| Aureolic acid \| 18378-89-7 \| Mithramycinum \| Mithramycine \| Plicamycine \| Plicamycinum \| Mitramycin \| Aurelic acid \| CHEBI:31856 \| Antibiotic LA 7017 \| CHEMBL257619 \| NIJ123W41V \| Mitramycine \| Mitramycinum \| Aurlelic acid \| A-2371 \| Plicam
Specifications & Purity	Moligand™, ≥95%
Biochemical and Physiological Mechanisms	Anticancer 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 Temp	Store at -20°C,Argon charged
Shipped In	Ice chest + Ice pads
Grade	Moligand™
Note	Wherever 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)

FLI1 Tbio Friend leukemia integration 1 transcription factor (0 Activities)

Discover Target: FLI1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ASPH Tchem Aspartyl/asparaginyl beta-hydroxylase (0 Activities)

Discover Target: ASPH

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

A673 (619 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DU-145 (51482 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PANC-1 (6144 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PC-3 (62116 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A549 (127892 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HCT-116 (91556 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Prostatic carcinoma cell (85 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LNCaP (8286 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HeLa (62764 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DMS-114 (15429 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

U-118-MG (352 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ES8 (149 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ES7 (149 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EWSR1 Tbio Friend leukemia integration 1 transcription factor (Proto-oncogene Fli-1)/RNA-binding protein EWS (19 Activities)

Discover Target: EWSR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TC-32 (111 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

VCaP (1078 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ASPH Tchem Aspartyl/asparaginyl beta-hydroxylase (62 Activities)

Discover Target: ASPH

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Database links

PubChem CID	163659
DrugBank Ligand	DB06810
Wikipedia	Plicamycin
CAS Registry No.	18378-89-7
ChEBI	CHEBI:31856
RCSB PDB Ligand	QWP
DrugCentral Ligand	2223

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

To view the certificate results,please click on a Lot number.For Lot numbers from past orders,please use our order status section

5 results found

Lot Number	Certificate Type	Date	Item
E2225243	Certificate of Analysis	Feb 23, 2024	P113149
E2225244	Certificate of Analysis	Feb 23, 2024	P113149
E2225253	Certificate of Analysis	Feb 23, 2024	P113149
L2109072	Certificate of Analysis	Sep 21, 2023	P113149
L2109073	Certificate of Analysis	Sep 21, 2023	P113149

Chemical and Physical Properties

Solubility	Soluble in phosphate buffered saline (1 mg/ml), ethanol, ethyl acetate, lower alcohols, and acetone. Insoluble in water.
Sensitivity	light 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

Citations of This Product

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:]

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]
18. Mary Zhang,Aarti Mathur,Yuwei Zhang,Sichuan Xi,Scott Atay,Julie A Hong,Nicole Datrice,Trevor Upham,Clinton D Kemp,R Taylor Ripley,Gordon Wiegand,Itzak Avital,Patricia Fetsch,Haresh Mani,Daniel Zlott,Robert Robey,Susan E Bates,Xinmin Li,Mahadev Rao,David S Schrump. (2012-07-04) Mithramycin represses basal and cigarette smoke-induced expression of ABCG2 and inhibits stem cell signaling in lung and esophageal cancer cells.. Cancer research, 72 ((16)): (4178-4192). [PMID:22751465]
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:]

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SKU	Size	Availability	Price
P113149-1mg	1mg	In stock	$167.90
P113149-5mg	5mg	In stock	$513.90
P113149-25mg	25mg	In stock	$1,761.90

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