Diprotin A

Names

[ Name ]:
Diprotin A

[Synonym ]:
MFCD00038707
H-ILE-PRO-ILE-OH
ILE-PRO-ILE H2O
Ile-Pro-Ile-OH
H-ILE-PRO-ILE-OH H2O
DIPEPTIDYLPEPTIDASE IV INHIBITOR I
L-Isoleucyl-L-prolyl-L-isoleucine
ILE-PRO-ILE
L-Ile-L-Pro-L-Ile-OH

Biological Activity

[Description]:

Diprotin A (Ile-Pro-Ile) is an inhibitor of dipeptidyl peptidase IV (DPP-IV)[1].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Dipeptidyl Peptidase

Research Areas >> Metabolic Disease

[Target]

IC50: DPP-IV[1]

[In Vitro]

Diprotin A (100 μM; 30 minutes after CXCR4-blocker or Src-inhibitor treatment) induces the phosphorylation of Src [Tyr 416] and VE-cadherin [Tyr731] in hECs in both normoxia and H/R conditions in human endothelial cells and disrupts endothelial cell-to-cell junctions, which are attenuated by CXCR4 (receptor of SDF-1α)-blocker or Src-inhibitor[1]. Western Blot Analysis[1] Cell Line: Human endothelial cells[1] Concentration: 100 μM Incubation Time: 30 minutes after CXCR4-blocker or Src-inhibitor treatment Result: Induced the phosphorylation of Src [Tyr 416] and VE-cadherin [Tyr731] in hECs.

[In Vivo]

Diprotin A (intraperitoneal injection; 70 μg/kg; twice daily; 7 days) increases the phosphorylation of Src and VE-cadherin and aggravates vascular leakage in the retinas. Collectively, Diprotin A induces vascular leakage by augmenting the SDF-1α/CXCR4/Src/VE-cadherin signaling pathway[1]. Animal Model: Streptozotocin-induced diabetic retinopathy model in wild-type C57/BL6 mice[1] Dosage: 70 μg/kg Administration: Intraperitoneal injection; twice daily; 7 days Result: Induced vascular leakage by augmenting the SDF-1α/CXCR4/Src/VE-cadherin signaling pathway.

[References]

[1]. Lee CS, et al. Dipeptidyl Peptidase-4 Inhibitor Increases Vascular Leakage in Retina through VE-cadherin Phosphorylation. Sci Rep. 2016 Jul 6;6:29393.

Chemical & Physical Properties

[ Density]:
1.14 g/cm3

[ Boiling Point ]:
583.1ºC at 760 mmHg

[ Molecular Formula ]:
C₁₇H₃₁N₃O₄

[ Molecular Weight ]:
341.44600

[ Flash Point ]:
306.5ºC

[ Exact Mass ]:
341.23100

[ PSA ]:
112.73000

[ LogP ]:
1.99540

[ Index of Refraction ]:
1.517

[ Storage condition ]:
−20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NR4737000

CHEMICAL NAME :: L-Isoleucine, N-(1-L-isoleucyl-L-prolyl)-

CAS REGISTRY NUMBER :: 90614-48-5

LAST UPDATED :: 199212

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C17-H31-N3-O4

MOLECULAR WEIGHT :: 341.51

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 37,422,1984

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
NR4737000

Articles

In vitro assessment of the multifunctional bioactive potential of Alaska pollock skin collagen following simulated gastrointestinal digestion.

J. Sci. Food Agric. 95(7) , 1514-20, (2015)

Dietary mineral deficiency, hypertension and diabetes have become serious human health problems. Dietary approaches are increasingly being investigated to address these issues. Identification of food-...

Antidiabetic property of Symplocos cochinchinensis is mediated by inhibition of alpha glucosidase and enhanced insulin sensitivity.

PLoS ONE 9(9) , e105829, (2014)

The study is designed to find out the biochemical basis of antidiabetic property of Symplocos cochinchinensis (SC), the main ingredient of 'Nisakathakadi' an Ayurvedic decoction for diabetes. Since di...

Utilisation of the isobole methodology to study dietary peptide-drug and peptide-peptide interactive effects on dipeptidyl peptidase IV (DPP-IV) inhibition.

Food Funct. 6(1) , 313-20, (2015)

Inhibition of dipeptidyl peptidase-IV (DPP-IV) is used as a means to regulate post-prandial serum glucose in type 2 diabetics. The effect of drug (Sitagliptin®)/peptide and binary peptide mixtures on ...

Related Compounds

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