 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C270H401N73O83S7 |
| Molecular Weight | 6221.96723999994 |
| Exact Mass | 6219.751 |
| CAS # | 62253-63-8 |
| Related CAS # | Epidermal growth factor (EGF) (phosphate) |
| PubChem CID | 16143379 |
| Appearance | Typically exists as solid at room temperature |
| LogP | -17.3 |
| Hydrogen Bond Donor Count | 94 |
| Hydrogen Bond Acceptor Count | 98 |
| Rotatable Bond Count | 203 |
| Heavy Atom Count | 433 |
| Complexity | 15800 |
| Defined Atom Stereocenter Count | 51 |
| SMILES | CC[C@H](C)[C@@H](C(=O)NCC(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)N[C@@H](CC4=CNC5=CC=CC=C54)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)[C@H](CC6=CC=C(C=C6)O)NC(=O)CNC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CC7=CC=C(C=C7)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC8=CC=C(C=C8)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC9=CN=CN9)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC1=CC=C(C=C1)O)NC(=O)CNC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CS)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)N)N |
| InChi Key | GVUGOAYIVIDWIO-UFWWTJHBSA-N |
| InChi Code | InChI=1S/C270H401N73O83S7/c1-24-134(19)217(262(420)293-112-201(355)298-161(69-74-205(359)360)229(387)301-160(45-35-82-286-269(279)280)228(386)333-192(119-428)255(413)307-162(68-73-198(274)352)230(388)316-176(94-141-54-64-150(350)65-55-141)241(399)304-159(44-34-81-285-268(277)278)227(385)325-186(105-212(373)374)248(406)313-169(87-127(5)6)235(393)302-158(43-31-33-80-272)226(384)318-179(97-144-108-289-156-41-29-27-39-153(144)156)243(401)319-178(96-143-107-288-155-40-28-26-38-152(143)155)242(400)305-164(71-76-207(363)364)231(389)312-170(88-128(7)8)236(394)310-167(267(425)426)46-36-83-287-270(281)282)341-250(408)174(92-139-50-60-148(348)61-51-139)300-203(357)113-292-261(419)214(131(13)14)340-264(422)216(133(17)18)339-259(417)195(122-431)335-246(404)182(101-200(276)354)322-257(415)191(118-427)332-220(378)137(22)297-234(392)175(93-140-52-62-149(349)63-53-140)315-225(383)157(42-30-32-79-271)303-247(405)185(104-211(371)372)326-237(395)168(86-126(3)4)311-219(377)136(21)296-224(382)163(70-75-206(361)362)309-265(423)218(135(20)25-2)342-251(409)177(95-142-56-66-151(351)67-57-142)317-233(391)166(78-85-433-23)308-256(414)194(121-430)336-263(421)215(132(15)16)338-204(358)114-291-223(381)184(103-210(369)370)323-244(402)180(98-145-109-283-124-294-145)320-238(396)171(89-129(9)10)314-258(416)193(120-429)334-240(398)173(91-138-48-58-147(347)59-49-138)299-202(356)111-290-222(380)183(102-209(367)368)324-245(403)181(99-146-110-284-125-295-146)321-254(412)190(117-346)330-239(397)172(90-130(11)12)328-260(418)197-47-37-84-343(197)266(424)196(123-432)337-232(390)165(72-77-208(365)366)306-252(410)189(116-345)331-249(407)187(106-213(375)376)327-253(411)188(115-344)329-221(379)154(273)100-199(275)353/h26-29,38-41,48-67,107-110,124-137,154,157-197,214-218,288-289,344-351,427-432H,24-25,30-37,42-47,68-106,111-123,271-273H2,1-23H3,(H2,274,352)(H2,275,353)(H2,276,354)(H,283,294)(H,284,295)(H,290,380)(H,291,381)(H,292,419)(H,293,420)(H,296,382)(H,297,392)(H,298,355)(H,299,356)(H,300,357)(H,301,387)(H,302,393)(H,303,405)(H,304,399)(H,305,400)(H,306,410)(H,307,413)(H,308,414)(H,309,423)(H,310,394)(H,311,377)(H,312,389)(H,313,406)(H,314,416)(H,315,383)(H,316,388)(H,317,391)(H,318,384)(H,319,401)(H,320,396)(H,321,412)(H,322,415)(H,323,402)(H,324,403)(H,325,385)(H,326,395)(H,327,411)(H,328,418)(H,329,379)(H,330,397)(H,331,407)(H,332,378)(H,333,386)(H,334,398)(H,335,404)(H,336,421)(H,337,390)(H,338,358)(H,339,417)(H,340,422)(H,341,408)(H,342,409)(H,359,360)(H,361,362)(H,363,364)(H,365,366)(H,367,368)(H,369,370)(H,371,372)(H,373,374)(H,375,376)(H,425,426)(H4,277,278,285)(H4,279,280,286)(H4,281,282,287)/t134-,135-,136-,137-,154-,157-,158-,159-,160-,161-,162-,163-,164-,165-,166-,167-,168-,169-,170-,171-,172-,173-,174-,175-,176-,177-,178-,179-,180-,181-,182-,183-,184-,185-,186-,187-,188-,189-,190-,191-,192-,193-,194-,195-,196-,197-,214-,215-,216-,217-,218-/m0/s1 |
| Chemical Name | (4S)-5-[[(2S)-1-[[(2R)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(1S)-4-carbamimidamido-1-carboxybutyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-[[2-[[(2S,3S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-4-amino-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-3-carboxy-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-carboxy-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[2-[[(2S)-3-carboxy-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[2-[[(2S)-3-carboxy-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2R)-2-[[(2S)-4-carboxy-2-[[(2S)-2-[[(2S)-3-carboxy-2-[[(2S)-2-[[(2S)-2,4-diamino-4-oxobutanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]-3-hydroxypropanoyl]amino]butanoyl]amino]-3-sulfanylpropanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]propanoyl]amino]acetyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]propanoyl]amino]acetyl]amino]-3-methylbutanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]butanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-3-sulfanylpropanoyl]amino]-4-oxobutanoyl]amino]-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]acetyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]-5-oxopentanoic acid |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Apoptosis, ROS[1][2]. |
| ln Vitro | In A431 cells, epidermal growth factor (EGF) (500 ng/mL; 0–20 minutes) might cause ROS generation [1]. A431 cells expressing exogenous catalase completely inhibited the tyrosine phosphorylation of several cellular proteins caused by epidermal growth factor (EGF) [1]. |
| ln Vivo | In male mice, the application of 10 pg/day of epidermal growth factor (EGF) via an osmotic pump for eight days resulted in a highly substantial stimulatory effect on wound closure [3]. |
| Animal Protocol |
Animal/Disease Models: C57BL6J and CBA mice (0.5-cm2 full-thickness back wound was cut out of the center of the back)[3] Doses: 10 μg /day Route of Administration: Osmotic pump delivered over 8 days at 10 pg/day Experimental Results: demonstrated a highly significant (P < 0.001) stimulatory effect on wound closure over 6 days in male mice. |
| References |
[1]. Bae YS, et al. Epidermal growth factor (EGF)-induced generation of hydrogen peroxide. Role in EGF receptor-mediated tyrosine phosphorylation. J Biol Chem. 1997 Jan 3;272(1):217-21. [2]. Henson ES, Gibson SB. Surviving cell death through epidermal growth factor (EGF) signal transduction pathways: implications for cancer therapy. Cell Signal. 2006 Dec;18(12):2089-97. [3]. Niall M, Ryan GB, O'Brien BM. The effect of epidermal growth factor on wound healing in mice. J Surg Res. 1982 Aug;33(2):164-9. |
| Additional Infomation |
Nepidermin is a recombinant form of the naturally-occurring polypeptide human epidermal growth factor with potential epithelial regenerative and cytoprotective activities. Upon topical application, recombinant human epidermal growth factor (rhEGF) may stimulate epithelial proliferation, differentiation and migration, which may result in the acceleration of epithelial regeneration and wound healing. In addition, rhEGF may attenuate epithelial cytotoxicities related to chemotherapy and/or radiotherapy. See also: Human epidermal growth factor (annotation moved to). |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.1607 mL | 0.8036 mL | 1.6072 mL | |
| 5 mM | 0.0321 mL | 0.1607 mL | 0.3214 mL | |
| 10 mM | 0.0161 mL | 0.0804 mL | 0.1607 mL |