C9705

Concanamycin A

Name: Concanamycin A
Brand: SIGMA

≥70% (HPLC), crystals, vacuolar-type v-ATPase inhibitor

Synonym(s):

Folimycin

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About This Item

Empirical Formula (Hill Notation):

C₄₆H₇₅NO₁₄

CAS Number:

80890-47-7

Molecular Weight:

866.09

NACRES:

NA.77

PubChem Substance ID:

24893186

UNSPSC Code:

12352200

MDL number:

MFCD00210037

Beilstein/REAXYS Number:

3560277

Product Name

Concanamycin A, ≥70% (HPLC)

InChI

1S/C46H75NO14/c1-13-16-34-28(7)37(58-38-22-33(48)43(31(10)57-38)60-45(47)53)23-46(54,61-34)30(9)41(51)29(8)42-35(55-11)18-15-17-24(3)19-26(5)39(49)32(14-2)40(50)27(6)20-25(4)21-36(56-12)44(52)59-42/h13,15-18,20-21,26-35,37-43,48-51,54H,14,19,22-23H2,1-12H3,(H2,47,53)/b16-13+,18-15+,24-17+,25-20+,36-21-/t26?,27?,28-,29?,30?,31-,32?,33-,34?,35?,37-,38+,39?,40?,41?,42?,43-,46+/m1/s1

SMILES string

CCC1C(O)C(C)C\C(C)=C\C=C\C(OC)C(OC(=O)\C(OC)=C\C(C)=C\C(C)C1O)C(C)C(O)C(C)[C@]2(O)C[C@@H](O[C@H]3C[C@@H](O)[C@H](OC(N)=O)[C@@H](C)O3)[C@H](C)C(O2)\C=C\C

InChI key

DJZCTUVALDDONK-LWLXYWDNSA-N

assay

≥70% (HPLC)

form

solid film

antibiotic activity spectrum

viruses

mode of action

enzyme | inhibits

storage temp.

−20°C

Quality Level

200

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Related Categories

Antibiotics

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Biochemicals

Cell Culture Supplements & Reagents

Application

Concanamycin A has been used:

as a lysosomal inhibitor in young and old fibroblasts
as a vacuolar-type H⁺-ATPase inhibitor in presynaptic vesicles
as a lysosomal acidification blocker in HepG2 hepatocytes cells

Biochem/physiol Actions

Concanamycin A (ConA) inhibits acidification of organelles and perforin-mediated cytotoxicity. It is a vacuolar-type v-ATPase inhibitor. ConA possesses antiprotozoal and antineoplastic properties. It mediates inhibition of the negative factor (Nef) protein of the human immunodeficiency virus.

General description

Chemical structure: macrolide

Concanamycin A belongs to the plecomacrolide family and comprises an 18-membered tetraenic macrolide ring.

pictograms

GHS06

signalword

Danger

hcodes

H300 + H310 + H330,H319

pcodes

P262 - P280 - P301 + P310 + P330 - P302 + P352 + P310 - P304 + P340 + P310 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Eye Irrit. 2

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 P2 (EN 143) respirator cartridges

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Macroautophagy is impaired in old murine brain tissue as well as in senescent human fibroblasts.

Christiane Ott et al.

Redox biology, 10, 266-273 (2016-11-09)

The overall decrease in proteolytic activity in aging can promote and accelerate protein accumulation and metabolic disturbances. To specifically analyze changes in macroautophagy (MA) we quantified different autophagy-related proteins (ATGs) in young, adult and old murine tissue as well as

Perforin-dependent cytotoxic mechanism in killing by CD8 positive T cells in ginbuna crucian carp, Carassius auratus langsdorfii.

Hideaki Toda et al.

Developmental and comparative immunology, 35(1), 88-93 (2010-09-04)

T cell-mediated cytotoxicity occurs via pathways based on perforin or Fas mechanisms. Perforin is a protein present in the cytoplasmic granules of CD8(+) cytotoxic T lymphocytes and is secreted to form pores on target cell membranes. In fish, although the

Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449.

Stephen F Haydock et al.

Microbiology (Reading, England), 151(Pt 10), 3161-3169 (2005-10-07)

The macrolide antibiotic concanamycin A has been identified as an exceptionally potent inhibitor of the vacuolar (V-type) ATPase. Such compounds have been mooted as the basis of a potential drug treatment for osteoporosis, since the V-ATPase is involved in the

Concanamycin A counteracts HIV-1 Nef to enhance immune clearance of infected primary cells by cytotoxic T lymphocytes.

Mark M Painter et al.

Proceedings of the National Academy of Sciences of the United States of America, 117(38), 23835-23846 (2020-09-10)

Nef is an HIV-encoded accessory protein that enhances pathogenicity by down-regulating major histocompatibility class I (MHC-I) expression to evade killing by cytotoxic T lymphocytes (CTLs). A potent Nef inhibitor that restores MHC-I is needed to promote immune-mediated clearance of HIV-infected

Identification of autophagosome-associated proteins and regulators by quantitative proteomic analysis and genetic screens.

Jörn Dengjel et al.

Molecular & cellular proteomics : MCP, 11(3), M111-M111 (2012-02-09)

Autophagy is one of the major intracellular catabolic pathways, but little is known about the composition of autophagosomes. To study the associated proteins, we isolated autophagosomes from human breast cancer cells using two different biochemical methods and three stimulus types:

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