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Merck

K3394

Sigma-Aldrich

KH7

≥98% (HPLC)

Synonym(s):

(E)-2-(1H-Benzo[d]imidazol-2-ylthio)-N′-(5-bromo-2-hydroxybenzylidene)propanehydrazide

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About This Item

Empirical Formula (Hill Notation):
C17H15BrN4O2S
CAS Number:
330676-02-3
Molecular Weight:
419.30
MDL number:
MFCD01230899
UNSPSC Code:
41106305
PubChem Substance ID:
329817136
NACRES:
NA.77

Key Documents

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Quality Level

100

Assay

≥98% (HPLC)

form

powder

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

CC(Sc1nc2ccccc2[nH]1)C(=O)N\N=C\c3cc(Br)ccc3O

InChI

1S/C17H15BrN4O2S/c1-10(25-17-20-13-4-2-3-5-14(13)21-17)16(24)22-19-9-11-8-12(18)6-7-15(11)23/h2-10,23H,1H3,(H,20,21)(H,22,24)/b19-9+

InChI key

WILMXUAKQKGGCC-DJKKODMXSA-N

Related Categories

Application

KH7 has been used:
  • as a soluble adenyl cyclase (sAC) antagonist to study its effect on the signaling pathway mediated by the action of transient  receptor type 1 (TRPV1) in sperm cells.
  • as a selective sAC antagonist to study its effect on the signaling pathway of proton gated channels (HV1) induced action in sperm cells.
  • as a sAC inhibitor to study its effects on cAMP increase in monophosphorylated myosin light chain (pMLC).

KH7 is not active against sAC in the presence of detergents. When used in cellular experiments, KH7 exhibits non-specific membrane disruption effects at concentrations above 50 μM.

Biochem/physiol Actions

KH7 is a selective inhibitor of soluble adenylyl cyclase.
KH7 is a selective inhibitor of soluble adenylyl cyclase. Soluble adenylyl cyclase (sAC) is an ubiquitously expressed, essential component of cAMP-signaling.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Adenylyl cyclases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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

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Certificates of Analysis (COA)

Lot/Batch Number
057M4616V
054M4615V
089K46121
089K4612

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Carresse L Gerald et al.
Alcoholism, clinical and experimental research, 40(2), 273-283 (2016-02-05)
Farm workers in rural areas consume more alcohol than those who reside in urban areas. Occupational exposures such as agricultural work can pose hazards on the respiratory system. It is established that hog barn dust induces inflammation in the airway
Naveen Kumar et al.
Molecular and cellular biochemistry, 430(1-2), 115-125 (2017-02-18)
Despite the current progress in cancer research and therapy, breast cancer remains the leading cause of mortality among half a million women worldwide. Migration and invasion of cancer cells are associated with prevalent tumor metastasis as well as high mortality.
Frances Evans et al.
Journal of cellular physiology, 235(3), 2947-2962 (2019-09-20)
In previous work, we reported that plasma membrane potential depolarization (PMPD) provokes cortical F-actin remodeling in bovine corneal endothelial (BCE) cells in culture, which eventually leads to the appearance of intercellular gaps. In kidney epithelial cells it has been shown
Xiudan Wang et al.
Fish & shellfish immunology, 66, 140-147 (2017-05-10)
Ocean acidification (OA) has deleterious impacts on immune response and energy homeostasis status of Mollusca. In the present study, the apoptosis ratio of hemocytes and the adenosine triphosphate (ATP) allocation in gill tissues were determined after Pacific oysters Crassostrea gigas
Mandy Lo et al.
Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology, 191(1), 113-125 (2020-11-21)
We tested in six fish species [Pacific lamprey (Lampetra richardsoni), Pacific spiny dogfish (Squalus suckleyi), Asian swamp eel (Monopterus albus), white sturgeon (Acipenser transmontanus), zebrafish (Danio rerio), and starry flounder (Platichthys stellatus)] the hypothesis that elevated extracellular [HCO3-] protects spontaneous
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