Diprotin A | CAS#90614-48-5 | Dipeptidyl Aminopeptidase IV Antagonist

MedKoo Cat#: 597383 | Name: Diprotin A

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Diprotin A is a dipeptidyl aminopeptidase IV antagonist from Bacillus cereus BMF673-RF1.

Chemical Structure

Diprotin A

CAS#90614-48-5

Theoretical Analysis

MedKoo Cat#: 597383

Name: Diprotin A

CAS#: 90614-48-5

Chemical Formula: C17H31N3O4

Exact Mass: 341.2315

Molecular Weight: 341.45

Elemental Analysis: C, 59.80; H, 9.15; N, 12.31; O, 18.74

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 585.00	2 Weeks
100mg	USD 950.00	2 Weeks

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Synonym

Diprotin A; Ile-Pro-Ile; H-Ile-Pro-Ile-OH; isoleucylprolylisoleucine; isoleucyl-prolyl-isoleucine; L-Isoleucyl-L-prolyl-L-isoleucine

IUPAC/Chemical Name

(2S,3S)-2-[[(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-3-methylpentanoic acid

InChi Key

JNTMAZFVYNDPLB-PEDHHIEDSA-N

InChi Code

InChI=1S/C17H31N3O4/c1-5-10(3)13(18)16(22)20-9-7-8-12(20)15(21)19-14(17(23)24)11(4)6-2/h10-14H,5-9,18H2,1-4H3,(H,19,21)(H,23,24)/t10-,11-,12-,13-,14-/m0/s1

SMILES Code

CC[C@H](C)[C@@H](C(O)=O)NC([C@H]1N(C([C@H]([C@@H](C)CC)N)=O)CCC1)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

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

In vitro activity:

To test whether DPP4-inhibitors would increase vascular permeability, this study treated hECs with diprotin A (DipA; a chemical inhibitor of DPP4) and assessed the phosphorylation of Src and VE-cadherin. H/R on hECs induced the phosphorylation of Src [Tyr 416] and VE-cadherin [Tyr731] (Fig. 3a–c). The phosphorylation of Src [Tyr416] and VE-cadherin [Tyr731] was further increased by DPP4-inhibitor. Reference: Sci Rep. 2016 Jul 6;6:29393. https://pubmed.ncbi.nlm.nih.gov/27381080/

In vivo activity:

Statistical analysis of staining images in the five groups showed that vascular area and length were increased in the DA (diprotin A)-treated group compared with the control group, but decreased in the group that received both DA and XAV-939, indicating that DA did affect the peripheral vessels of the cerebral infarct, thereby reducing the degree of vascular injury and improving vascular remodeling (Figures 4B,C). Reference: Front Neurosci. 2022 May 9;16:861059. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9125038/

	Solvent	mg/mL	mM
Solubility
	DMSO	250.0	732.17
	Water	67.1	196.44

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 341.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Lee CS, Kim YG, Cho HJ, Park J, Jeong H, Lee SE, Lee SP, Kang HJ, Kim HS. Dipeptidyl Peptidase-4 Inhibitor Increases Vascular Leakage in Retina through VE-cadherin Phosphorylation. Sci Rep. 2016 Jul 6;6:29393. doi: 10.1038/srep29393. PMID: 27381080; PMCID: PMC4933943. 2. Zhou MY, Zhang YJ, Ding HM, Wu WF, Cai WW, Wang YQ, Geng DQ. Diprotin A TFA Exerts Neurovascular Protection in Ischemic Cerebral Stroke. Front Neurosci. 2022 May 9;16:861059. doi: 10.3389/fnins.2022.861059. PMID: 35615279; PMCID: PMC9125038. 3. Robinson MV, Mel'nikova EV, Trufakin VA. Effect of Diprotin A, an Inhibitor of Dipeptidyl Peptidase IV, on Immunological Parameters of Lymphocytes in Intact Animals and Animals with Experimental Autoimmune Process. Bull Exp Biol Med. 2015 Apr;158(6):769-71. doi: 10.1007/s10517-015-2858-0. Epub 2015 Apr 21. PMID: 25894775.

In vitro protocol:

In vivo protocol:

1. Zhou MY, Zhang YJ, Ding HM, Wu WF, Cai WW, Wang YQ, Geng DQ. Diprotin A TFA Exerts Neurovascular Protection in Ischemic Cerebral Stroke. Front Neurosci. 2022 May 9;16:861059. doi: 10.3389/fnins.2022.861059. PMID: 35615279; PMCID: PMC9125038. 2. Robinson MV, Mel'nikova EV, Trufakin VA. Effect of Diprotin A, an Inhibitor of Dipeptidyl Peptidase IV, on Immunological Parameters of Lymphocytes in Intact Animals and Animals with Experimental Autoimmune Process. Bull Exp Biol Med. 2015 Apr;158(6):769-71. doi: 10.1007/s10517-015-2858-0. Epub 2015 Apr 21. PMID: 25894775.

1: Zhou MY, Zhang YJ, Ding HM, Wu WF, Cai WW, Wang YQ, Geng DQ. Diprotin A TFA Exerts Neurovascular Protection in Ischemic Cerebral Stroke. Front Neurosci. 2022 May 9;16:861059. doi: 10.3389/fnins.2022.861059. PMID: 35615279; PMCID: PMC9125038. 2: Rahfeld J, Schierhorn M, Hartrodt B, Neubert K, Heins J. Are diprotin A (Ile- Pro-Ile) and diprotin B (Val-Pro-Leu) inhibitors or substrates of dipeptidyl peptidase IV? Biochim Biophys Acta. 1991 Jan 29;1076(2):314-6. doi: 10.1016/0167-4838(91)90284-7. PMID: 1671823. 3: Rónai AZ, Timár J, Makó E, Erdö F, Gyarmati Z, Tóth G, Orosz G, Fürst S, Székely JI. Diprotin A, an inhibitor of dipeptidyl aminopeptidase IV(EC 3.4.14.5) produces naloxone-reversible analgesia in rats. Life Sci. 1999;64(2):145-52. doi: 10.1016/s0024-3205(98)00544-x. PMID: 10069492. 4: Khlebnikova NN, Orshanskaya EV, Narkevich VB, Kudrin VS, Krupina NA. Dipeptidyl Peptidase 4 Inhibitors Diprotin A and Sitagliptin Administered on Weeks 2-3 of Postnatal Development Modulate Monoamine Metabolism in the Striatum of Adult Rats. Bull Exp Biol Med. 2017 Jun;163(2):190-194. doi: 10.1007/s10517-017-3763-5. Epub 2017 Jul 18. PMID: 28726205. 5: Balogh M, Varga BK, Karádi DÁ, Riba P, Puskár Z, Kozsurek M, Al-Khrasani M, Király K. Similarity and dissimilarity in antinociceptive effects of dipeptidyl- peptidase 4 inhibitors, Diprotin A and vildagliptin in rat inflammatory pain models following spinal administration. Brain Res Bull. 2019 Apr;147:78-85. doi: 10.1016/j.brainresbull.2019.02.001. Epub 2019 Feb 7. PMID: 30738866. 6: Robinson MV, Mel'nikova EV, Trufakin VA. Effect of Diprotin A, an Inhibitor of Dipeptidyl Peptidase IV, on Immunological Parameters of Lymphocytes in Intact Animals and Animals with Experimental Autoimmune Process. Bull Exp Biol Med. 2015 Apr;158(6):769-71. doi: 10.1007/s10517-015-2858-0. Epub 2015 Apr 21. PMID: 25894775. 7: Kawai T, Choi U, Liu PC, Whiting-Theobald NL, Linton GF, Malech HL. Diprotin A infusion into nonobese diabetic/severe combined immunodeficiency mice markedly enhances engraftment of human mobilized CD34+ peripheral blood cells. Stem Cells Dev. 2007 Jun;16(3):361-70. doi: 10.1089/scd.2007.9997. PMID: 17610366. 8: Hiramatsu H, Yamamoto A, Kyono K, Higashiyama Y, Fukushima C, Shima H, Sugiyama S, Inaka K, Shimizu R. The crystal structure of human dipeptidyl peptidase IV (DPPIV) complex with diprotin A. Biol Chem. 2004 Jun;385(6):561-4. doi: 10.1515/BC.2004.068. PMID: 15255191. 9: Krupina NA, Khlebnikova NN, Orlova IN. [Emotional Motivational Disorders in Rats as a Result of Diprotin A and Sitagliptin Administration in the First Postnatal Week]. Zh Vyssh Nerv Deiat Im I P Pavlova. 2016 May;66(3):367-381. Russian. PMID: 30695419. 10: Francis P, Chakraborty K. Clathriketal, a new tricyclic spiroketal compound from marine sponge Clathria prolifera attenuates serine exopeptidase dipeptidyl peptidase-IV. Nat Prod Res. 2022 Jun;36(12):3069-3077. doi: 10.1080/14786419.2021.1956491. Epub 2021 Jul 27. PMID: 34315292. 11: Krupina NA, Khlebnikova NN. Omega-3 polyunsaturated fatty acids when administered to lactating rats modify the development of experimental anxiety- depressive state in the rat pups exposed to the dipeptidyl peptidase-IV inhibitor diprotin A on the second - third weeks after the birth. Patol Fiziol Eksp Ter. 2016 Oct-Dec;60(4):9-19. PMID: 29244917. 12: Chakraborty C, Hsu MJ, Agoramoorthy G. Understanding the molecular dynamics of type-2 diabetes drug target DPP-4 and its interaction with Sitagliptin and inhibitor Diprotin-A. Cell Biochem Biophys. 2014 Nov;70(2):907-22. doi: 10.1007/s12013-014-9998-0. PMID: 24809328. 13: Zhang D, Huang W, Dai B, Zhao T, Ashraf A, Millard RW, Ashraf M, Wang Y. Genetically manipulated progenitor cell sheet with diprotin A improves myocardial function and repair of infarcted hearts. Am J Physiol Heart Circ Physiol. 2010 Nov;299(5):H1339-47. doi: 10.1152/ajpheart.00592.2010. Epub 2010 Aug 27. PMID: 20802132; PMCID: PMC2993193. 14: Bagosi Z, Jászberényi M, Bujdosó E, Szabó G, Telegdy G. The effects of endomorphins and diprotin A on striatal dopamine release induced by electrical stimulation-an in vitro superfusion study in rats. Neurochem Int. 2006 Dec;49(7):665-8. doi: 10.1016/j.neuint.2006.05.006. Epub 2006 Jul 3. PMID: 16815593. 15: Wyss BK, Donnelly AF, Zhou D, Sinn AL, Pollok KE, Goebel WS. Enhanced homing and engraftment of fresh but not ex vivo cultured murine marrow cells in submyeloablated hosts following CD26 inhibition by Diprotin A. Exp Hematol. 2009 Jul;37(7):814-23. doi: 10.1016/j.exphem.2009.03.005. PMID: 19540435; PMCID: PMC2700780. 16: Singla RK, Kumar R, Khan S, Mohit, Kumari K, Garg A. Natural Products: Potential Source of DPP-IV Inhibitors. Curr Protein Pept Sci. 2019;20(12):1218-1225. doi: 10.2174/1389203720666190502154129. PMID: 31057098. 17: Sakurada C. [Development of a new analgesic based on metabolism of endomorphin, an endogenous opioid peptide]. Yakugaku Zasshi. 2004 Aug;124(8):549-54. Japanese. doi: 10.1248/yakushi.124.549. PMID: 15297724. 18: Gu LH, Liao LP, Hu HJ, Annie Bligh SW, Wang CH, Chou GX, Wang ZT. A thin- layer chromatography-bioautographic method for detecting dipeptidyl peptidase IV inhibitors in plants. J Chromatogr A. 2015 Sep 11;1411:116-22. doi: 10.1016/j.chroma.2015.07.123. Epub 2015 Aug 5. PMID: 26283532. 19: Kumar D, Hamse VK, Neema KN, Babu Shubha P, Chetan DM, Shivananju NS. Purification and biochemical characterization of a novel secretory dipeptidyl peptidase IV from porcine serum. Mol Cell Biochem. 2020 Aug;471(1-2):71-80. doi: 10.1007/s11010-020-03766-y. Epub 2020 Jun 23. PMID: 32577945. 20: Paulose SK, Chakraborty K. Anti-hyperglycemic Δ5 steroids, marginoids A-C from marine veined octopus Amphioctopus marginatus (Octopodidae): Prospective natural leads inhibit serineexopeptidase dipeptidyl peptidase-4. Steroids. 2022 Oct;186:109090. doi: 10.1016/j.steroids.2022.109090. Epub 2022 Jul 16. PMID: 35850257.