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SML0508

Sigma-Aldrich

Pentostatin

≥95% (HPLC)

Synonym(s):

(8R)-3-(2-Deoxy-β-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol, 2′-dCF, DCF, Deoxycoformycin

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About This Item

Empirical Formula (Hill Notation):
C11H16N4O4
CAS Number:
53910-25-1
Molecular Weight:
268.27
UNSPSC Code:
12352200
PubChem Substance ID:
329825517
NACRES:
NA.77

Assay

≥95% (HPLC)

form

powder

optical activity

[α]/D +70 to +80°, c = 1 in H2O

storage condition

desiccated

color

white to beige

solubility

H2O: 10 mg/mL, clear

shipped in

wet ice

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@H](C[C@@H]1O)n2cnc3[C@H](O)CN=CNc23

InChI

1S/C11H16N4O4/c16-3-8-6(17)1-9(19-8)15-5-14-10-7(18)2-12-4-13-11(10)15/h4-9,16-18H,1-3H2,(H,12,13)/t6-,7+,8+,9+/m0/s1

InChI key

FPVKHBSQESCIEP-JQCXWYLXSA-N

Gene Information

human ... ADA(100)

Application

Pentostatin has been used in in vivo anti-tumor studies. It has also been used along with cyclophosphamide as a selective B-cell immune suppression regimen to explore solid tumor therapy by selectively targeting stromal endothelial cells.

Biochem/physiol Actions

Pentostatin is a ring-expanded nucleoside (REN) that potently inhibits adenosine deaminase, which leads to lymphocyte toxicity. Pentostatin is used as anticancer agent to treat leukemia (hairy cell leukemia and chronic lymphocytic leukemia) and is investigated as an agent to treat graft-versus-host disease (GVHD).
Pentostatin/2′-deoxycoformycin is used to treat patients with Waldenström′s macroglobulinemia.

Features and Benefits

This compound is featured on the Adenosine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Air sensitve; hygroscopic.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Behrouz Elahi et al.
Colloids and surfaces. B, Biointerfaces, 181, 830-836 (2019-06-30)
Bio-based synthesis of Nano-Ceria (NC) was performed in Linum usitatissimum L. (Lu) seeds extract as capping agent. Obtained gel was calcined at 400, 500, and 600 °C to investigate the effect of temperature on the size and morphology of the particles.
Youliang Zhao et al.
Environmental toxicology and pharmacology, 70, 103201-103201 (2019-06-16)
Early and accurate evaluation of immunotoxicity is crucial. However, there are few in vitro models for immunosuppressive evaluation. THP-1 cells has long been used for in vitro sensitivity evaluation. Whether it can be used for immunosuppressive evaluation remains unclear. In
Da-Tong Ju et al.
Nutrients, 11(7) (2019-07-25)
Vasicinone is a quinazoline alkaloid isolated from the Adhatoda vasica plant. In this study, we explored the neuroprotective effect and underlying molecular mechanism of vasicinone against paraquat-induced cellular apoptosis in SH-SY5Y cells. Vasicinone reduced the paraquat-induced loss of cell viability
Solid tumor therapy by selectively targeting stromal endothelial cells
Liu S, et al.
Proceedings of the National Academy of Sciences of the USA, 113(28), E4079-E4087 (2016)
Hairy-cell leukemia: induction of complete remission with pentostatin (2'-deoxycoformycin).
Spiers AS, et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 2(12), 1336-1342 (1984)
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