Pexiganan acetate | CAS#172820-23-4 | Antimicrobial peptide

MedKoo Cat#: 333099 | Name: Pexiganan acetate

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Description:

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

Pexiganan acetate, also known as MSI-78; is a synthetic antimicrobial peptide.1 It is active against various clinical isolates of bacteria from patients with diabetic foot infections, including S. aureus, methicillin-resistant S. aureus (MRSA), and P. aeruginosa (MICs = 16-32, 16-32, and 8-16 µg/ml, respectively). Pexiganan, exhibited bactericidal activity in vitro against Gram-positive and -negative isolates and was also shown to have a low potential for resistance development in broth serial passage experiments.

Chemical Structure

Pexiganan acetate

CAS#172820-23-4 (acetate)

Theoretical Analysis

MedKoo Cat#: 333099

Name: Pexiganan acetate

CAS#: 172820-23-4 (acetate)

Chemical Formula: C124H214N32O24

Exact Mass: 0.0000

Molecular Weight: 2537.28

Elemental Analysis: C, 58.70; H, 8.50; N, 17.67; O, 15.13

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 550.00	2 Weeks
25mg	USD 1,250.00	2 Weeks

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Related CAS #

172820-23-4 (acetate) 147664-63-9 (free base)

Synonym

Cytolex; GIGKFLKKAKKFGKAFVKILKKa; GIGKFLKKAKKFGKAFVKILKK-NH2; MSI-78; MSI 78; MSI78; Pexiganan acetate;

IUPAC/Chemical Name

glycyl-L-isoleucylglycyl-L-lysyl-L-phenylalanyl-L-leucyl-L-lysyl-L-lysyl-L-alanyl-L-lysyl-L-lysyl-L-phenylalanylglycyl-L-lysyl-L-alanyl-L-phenylalanyl-L-valyl-L-lysyl-L-isoleucyl-L-leucyl-L-lysyl-L-lysinamide, acetate

InChi Key

ZYMCXUWEZQKVIO-IJAHCEAPSA-N

InChi Code

InChI=1S/C122H210N32O22.C2H4O2/c1-13-77(9)102(152-98(155)71-132)120(174)135-73-100(157)139-86(50-26-35-59-125)110(164)150-96(69-82-44-20-16-21-45-82)118(172)148-93(66-74(3)4)116(170)145-90(54-30-39-63-129)113(167)142-87(51-27-36-60-126)109(163)137-79(11)105(159)141-88(52-28-37-61-127)112(166)143-91(55-31-40-64-130)114(168)149-95(68-81-42-18-15-19-43-81)107(161)134-72-99(156)138-85(49-25-34-58-124)108(162)136-80(12)106(160)147-97(70-83-46-22-17-23-47-83)119(173)153-101(76(7)8)121(175)146-92(56-32-41-65-131)115(169)154-103(78(10)14-2)122(176)151-94(67-75(5)6)117(171)144-89(53-29-38-62-128)111(165)140-84(104(133)158)48-24-33-57-123;1-2(3)4/h15-23,42-47,74-80,84-97,101-103H,13-14,24-41,48-73,123-132H2,1-12H3,(H2,133,158)(H,134,161)(H,135,174)(H,136,162)(H,137,163)(H,138,156)(H,139,157)(H,140,165)(H,141,159)(H,142,167)(H,143,166)(H,144,171)(H,145,170)(H,146,175)(H,147,160)(H,148,172)(H,149,168)(H,150,164)(H,151,176)(H,152,155)(H,153,173)(H,154,169);1H3,(H,3,4)/t77-,78-,79-,80-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,101-,102-,103-;/m0./s1

SMILES Code

NCCCC[C@@H](C(N)=O)NC([C@H](CCCCN)NC([C@H](CC(C)C)NC([C@H]([C@@H](C)CC)NC([C@H](CCCCN)NC([C@H](C(C)C)NC([C@H](CC1=CC=CC=C1)NC([C@H](C)NC([C@H](CCCCN)NC(CNC([C@H](CC2=CC=CC=C2)NC([C@H](CCCCN)NC([C@H](CCCCN)NC([C@H](C)NC([C@H](CCCCN)NC([C@H](CCCCN)NC([C@H](CC(C)C)NC([C@H](CC3=CC=CC=C3)NC([C@H](CCCCN)NC(CNC([C@H]([C@@H](C)CC)NC(CN)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O.CC(O)=O

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

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

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 2,537.28 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

1: Teixeira MA, Antunes JC, Seabra CL, Fertuzinhos A, Tohidi SD, Reis S, Amorim MTP, Ferreira DP, Felgueiras HP. Antibacterial and hemostatic capacities of cellulose nanocrystalline-reinforced poly(vinyl alcohol) electrospun mats doped with Tiger 17 and pexiganan peptides for prospective wound healing applications. Biomater Adv. 2022 Jun;137:212830. doi: 10.1016/j.bioadv.2022.212830. Epub 2022 Apr 29. PMID: 35929263. 2: Teixeira MA, Antunes JC, Seabra CL, Tohidi SD, Reis S, Amorim MTP, Felgueiras HP. Tiger 17 and pexiganan as antimicrobial and hemostatic boosters of cellulose acetate-containing poly(vinyl alcohol) electrospun mats for potential wound care purposes. Int J Biol Macromol. 2022 Jun 1;209(Pt A):1526-1541. doi: 10.1016/j.ijbiomac.2022.04.130. Epub 2022 Apr 22. PMID: 35469947. 3: Gomes D, Santos R, S Soares R, Reis S, Carvalho S, Rego P, C Peleteiro M, Tavares L, Oliveira M. Pexiganan in Combination with Nisin to Control Polymicrobial Diabetic Foot Infections. Antibiotics (Basel). 2020 Mar 20;9(3):128. doi: 10.3390/antibiotics9030128. PMID: 32244862; PMCID: PMC7148459. 4: Cirioni O, Simonetti O, Morroni G, Brescini L, Kamysz W, Kamysz E, Orlando F, Pierpaoli E, Caffarini M, Orciani M, Agostinelli C, Offidani A, Provinciali M, Giacometti A. Efficacy of Pexiganan Combination with Tigecycline in a Mouse Model of Pseudomonas aeruginosa Sepsis. Curr Top Med Chem. 2018;18(24):2127-2132. doi: 10.2174/1568026619666181219123431. PMID: 30569865. 5: Sun B, Wibowo D, Middelberg APJ, Zhao CX. Cost-effective downstream processing of recombinantly produced pexiganan peptide and its antimicrobial activity. AMB Express. 2018 Jan 24;8(1):6. doi: 10.1186/s13568-018-0541-3. PMID: 29368022; PMCID: PMC5783979. 6: Goldstein EJC, Citron DM, Tyrrell KL, Leoncio ES. In Vitro Activities of Pexiganan and 10 Comparator Antimicrobials against 502 Anaerobic Isolates Recovered from Skin and Skin Structure Infections. Antimicrob Agents Chemother. 2017 Nov 22;61(12):e01401-17. doi: 10.1128/AAC.01401-17. PMID: 28993327; PMCID: PMC5700356. 7: Goldstein EJC, Citron DM, Tyrrell KL, Leoncio ES. In Vitro Activity of Pexiganan and 10 Comparator Antimicrobials against 234 Isolates, Including 93 Pasteurella Species and 50 Anaerobic Bacterial Isolates Recovered from Animal Bite Wounds. Antimicrob Agents Chemother. 2017 May 24;61(6):e00246-17. doi: 10.1128/AAC.00246-17. PMID: 28373186; PMCID: PMC5444131. 8: Flamm RK, Rhomberg PR, Farrell DJ, Jones RN. In vitro spectrum of pexiganan activity; bactericidal action and resistance selection tested against pathogens with elevated MIC values to topical agents. Diagn Microbiol Infect Dis. 2016 Sep;86(1):66-9. doi: 10.1016/j.diagmicrobio.2016.06.012. Epub 2016 Jun 16. PMID: 27352729. 9: Jepson AK, Schwarz-Linek J, Ryan L, Ryadnov MG, Poon WC. What Is the 'Minimum Inhibitory Concentration' (MIC) of Pexiganan Acting on Escherichia coli?-A Cautionary Case Study. Adv Exp Med Biol. 2016;915:33-48. doi: 10.1007/978-3-319-32189-9_4. PMID: 27193536. 10: Cirioni O, Simonetti O, Pierpaoli E, Barucca A, Ghiselli R, Orlando F, Pelloni M, Minardi D, Trombettoni MM, Guerrieri M, Offidani A, Giacometti A, Provinciali M. Enhanced Efficacy of Combinations of Pexiganan with Colistin Versus Acinetobacter Baumannii in Experimental Sepsis. Shock. 2016 Aug;46(2):219-25. doi: 10.1097/SHK.0000000000000584. PMID: 26849630. 11: Zhang XL, Jiang AM, Ma ZY, Li XB, Xiong YY, Dou JF, Wang JF. The synthetic antimicrobial peptide pexiganan and its nanoparticles (PNPs) exhibit the anti- helicobacter pylori activity in vitro and in vivo. Molecules. 2015 Mar 2;20(3):3972-85. doi: 10.3390/molecules20033972. PMID: 25738539; PMCID: PMC6272436. 12: Flamm RK, Rhomberg PR, Simpson KM, Farrell DJ, Sader HS, Jones RN. In vitro spectrum of pexiganan activity when tested against pathogens from diabetic foot infections and with selected resistance mechanisms. Antimicrob Agents Chemother. 2015 Mar;59(3):1751-4. doi: 10.1128/AAC.04773-14. Epub 2015 Jan 12. PMID: 25583717; PMCID: PMC4325814. 13: Zhao CX, Dwyer MD, Yu AL, Wu Y, Fang S, Middelberg AP. A simple and low-cost platform technology for producing pexiganan antimicrobial peptide in E. coli. Biotechnol Bioeng. 2015 May;112(5):957-64. doi: 10.1002/bit.25505. Epub 2015 Jan 2. PMID: 25425208. 14: Kulkarni MM, Karafova A, Kamysz W, McGwire BS. Design of protease-resistant pexiganan enhances antileishmanial activity. Parasitol Res. 2014 May;113(5):1971-6. doi: 10.1007/s00436-014-3847-3. PMID: 24658630. 15: Cirioni O, Silvestri C, Ghiselli R, Kamysz W, Minardi D, Castelli P, Orlando F, Kamysz E, Provinciali M, Muzzonigro G, Guerrieri M, Giacometti A. In vitro and in vivo effects of sub-MICs of pexiganan and imipenem on Pseudomonas aeruginosa adhesion and biofilm development. Infez Med. 2013 Dec;21(4):287-95. PMID: 24335459. 16: Lee DK, Brender JR, Sciacca MF, Krishnamoorthy J, Yu C, Ramamoorthy A. Lipid composition-dependent membrane fragmentation and pore-forming mechanisms of membrane disruption by pexiganan (MSI-78). Biochemistry. 2013 May 14;52(19):3254-63. doi: 10.1021/bi400087n. Epub 2013 Apr 29. PMID: 23590672; PMCID: PMC3795814. 17: Gottler LM, Ramamoorthy A. Structure, membrane orientation, mechanism, and function of pexiganan--a highly potent antimicrobial peptide designed from magainin. Biochim Biophys Acta. 2009 Aug;1788(8):1680-6. doi: 10.1016/j.bbamem.2008.10.009. Epub 2008 Oct 29. PMID: 19010301; PMCID: PMC2726618. 18: Lipsky BA, Holroyd KJ, Zasloff M. Topical versus systemic antimicrobial therapy for treating mildly infected diabetic foot ulcers: a randomized, controlled, double-blinded, multicenter trial of pexiganan cream. Clin Infect Dis. 2008 Dec 15;47(12):1537-45. doi: 10.1086/593185. PMID: 18990064. 19: Gopinath D, Kumar MS, Selvaraj D, Jayakumar R. Pexiganan-incorporated collagen matrices for infected wound-healing processes in rat. J Biomed Mater Res A. 2005 Jun 1;73(3):320-31. doi: 10.1002/jbm.a.30303. PMID: 15800884. 20: Shanmugam G, Polavarapu PL, Gopinath D, Jayakumar R. The structure of antimicrobial pexiganan peptide in solution probed by Fourier transform infrared absorption, vibrational circular dichroism, and electronic circular dichroism spectroscopy. Biopolymers. 2005;80(5):636-42. doi: 10.1002/bip.20132. PMID: 15657879.