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Merck

A9400

7-Aminoactinomycin D

~97% (HPLC), powder, fluorescent DNA stain

Synonym(s):

7-AAD

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About This Item

Empirical Formula (Hill Notation):
C62H87N13O16
CAS Number:
7240-37-1
Molecular Weight:
1270.43
NACRES:
NA.77
PubChem Substance ID:
24891445
UNSPSC Code:
41106305
MDL number:
MFCD00077295
Beilstein/REAXYS Number:
5915844

Key Documents

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Product Name

7-Aminoactinomycin D, ~97% (HPLC), powder

InChI

1S/C62H87N13O16/c1-26(2)42-59(85)74-21-17-19-36(74)57(83)70(13)24-38(76)72(15)48(28(5)6)61(87)89-32(11)44(55(81)66-42)68-53(79)34-23-35(63)30(9)51-46(34)65-47-40(41(64)50(78)31(10)52(47)91-51)54(80)69-45-33(12)90-62(88)49(29(7)8)73(16)39(77)25-71(14)58(84)37-20-18-22-75(37)60(86)43(27(3)4)67-56(45)82/h23,26-29,32-33,36-37,42-45,48-49H,17-22,24-25,63-64H2,1-16H3,(H,66,81)(H,67,82)(H,68,79)(H,69,80)/t32-,33-,36+,37+,42-,43-,44+,45+,48+,49?/m1/s1

SMILES string

CC(C)[C@H]1NC(=O)[C@@H](NC(=O)c2cc(N)c(C)c3OC4=C(C)C(=O)C(N)=C(C(=O)N[C@H]5[C@@H](C)OC(=O)[C@@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]6CCCN6C(=O)[C@H](NC5=O)C(C)C)C4=Nc23)[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]7CCCN7C1=O

InChI key

YXHLJMWYDTXDHS-SGILFZQNSA-N

assay

~97% (HPLC)

form

powder

color

red to very dark purple

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes

storage temp.

2-8°C

Quality Level

300

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Application

7-Aminoactinomycin D has been used:
  • for nuclei visualization in mouse tail skin
  • as a nuclear stain in imaging flow cytometry for nucleus-protein colocalization
  • in flow cytometry to determine the level of CD16 (Fc gamma III receptor) and CD32 (Fc gamma II receptor) in epidermal cells

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

General description

7-Aminoactinomycin D (7-ADD), an analog of actinomycin D (AD) is a membrane-impermeable red fluorescent DNA dye. It can selectively bind GC regions of DNA. 7-ADD is used in flow cytometry to differentiate between viable, apoptotic, and late apoptotic/dead cells. This DNA stain finds its application in chromosome analysis, cell cycle studies, and quantification of apoptosis.
Chemical structure: peptide

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
049M4099V
126M4105V
039M4116V
039M4017V
059M4030V

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Changchun Du et al.
Journal for immunotherapy of cancer, 7(1), 207-207 (2019-08-08)
One of the mechanisms by which tumors evade immune surveillance is through shedding of the major histocompatibility complex (MHC) class I chain-related protein A and B (MICA/B) from their cell surface. MICA/B are ligands for the activating receptor NKG2D on
Anna Chipont et al.
Arteriosclerosis, thrombosis, and vascular biology, 39(2), 170-177 (2018-12-28)
Objective- To determine the role of microRNA-21 (miR-21) on the homeostasis of monocyte subsets and on atherosclerosis development in ApoE-/- (apolipoprotein E) mice. Approach and Results- In ApoE-/- mice, miR-21 expression was increased in circulating Ly-6Clo nonclassical monocytes in comparison
Yi Wei Bryan Teo et al.
Immunobiology, 224(4), 526-531 (2019-05-11)
Simulated Infective Protocol (SIP) is an ex-vivo culture system modeled after the temporal changes of essential cytokines in an acute infection, and previously proven successful in converting T lymphocytes harvested and activated from peripheral blood of normal donors, to revertant
Sabrina H L Hoffmann et al.
Theranostics, 9(20), 5869-5885 (2019-09-20)
Myeloid-derived suppressor cells (MDSCs) are immunosuppressive cells of the myeloid compartment and major players in the tumor microenvironment (TME). With increasing numbers of studies describing MDSC involvement in cancer immune escape, cancer metastasis and the dampening of immunotherapy responses, MDSCs
F S Peters et al.
Clinical and experimental immunology, 197(3), 341-351 (2019-05-07)
Cutaneous squamous cell carcinoma (cSCC) is a serious complication after organ transplantation and patients benefit from an early risk assessment. We hypothesized that functional differences in circulating T cells may represent risk factors for post-transplant cSCC development. Here, we analysed
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Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

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